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Information on EC 1.3.1.22 - 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+) and Organism(s) Homo sapiens

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EC Tree
IUBMB Comments
The enzyme catalyses the conversion of assorted 3-oxo-Delta4 steroids into their corresponding 5alpha form. Substrates for the mammalian enzyme include testosterone, progesterone, and corticosterone. Substrates for the plant enzyme are brassinosteroids such as campest-4-en-3-one and (22alpha)-hydroxy-campest-4-en-3-one. cf. EC 1.3.99.5, 3-oxo-5alpha-steroid 4-dehydrogenase (acceptor).
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This record set is specific for:
Homo sapiens
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Word Map
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
5alphar, 5 alpha-reductase type 2, 5alpha-reductase 1, 5alpha-r2, steroid 5-alpha reductase, steroid 5-alpha-reductase, 5-alpha-reductase type 2, 5 alpha-r2, 5-alpha-reductase type 1, steroid 5alpha-reductase type ii, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3-oxosteroid 5alpha-reductase
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3-oxosteroid DELTA4-dehydrogenase
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-
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4-ene-3-oxosteroid 5alpha-reductase
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4-ene-5alpha-reductase
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-
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5 alpha-R2
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5 alpha-reductase type 2
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5-alpha reductase I
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isozyme
5-alpha reductase II
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isozyme
5-alpha-reductase type 1
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isozyme
5-alpha-reductase type 2
5a-reductase type 1
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5a-reductase type 2
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5alpha-R1
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5alpha-R2
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5alpha-reductase 1
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5alpha-reductase II
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5alpha-reductase type 1
5alpha-reductase type 2
5alpha-SR2
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5alphaR
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5alphaR type 2
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cholest-4-en-3-one 5alpha-reductase
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cortisone alpha-reductase
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cortisone DELTA 4-5alphareductase
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DELTA4-3-ketosteroid 5alpha-oxidoreductase
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DELTA4-3-ketosteroid reductase (5alpha)
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DELTA4-3-oxosteroid-5 alpha-reductase
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DELTA4-5alpha-reductase
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DELTA4-steroid 5alpha-reductase (progesterone)
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microsomal steroid reductase (5alpha)
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NADPH:DELTA4-3-oxosteroid-5alpha-oxidoreductase
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progesterone 5alpha-reductase
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reduced nicotinamide adenine dinucleotide phosphate:DELTA4-3-ketosteroid 5alpha-oxidoreductase
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reductase, cholestenone 5alpha-
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reductase, cortisone DELTA: 4-5alpha-
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reductase, progesterone 5alpha-
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S5alphaR
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SRD5A1
SRD5A2
SRDA1
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steroid 5-alpha reductase
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steroid 5-alpha-reductase
steroid 5alpha reductase type 2
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steroid 5alpha-hydrogenase
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steroid 5alpha-reductase
steroid 5alpha-reductase type II
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testosterone 5alpha-reductase
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testosterone delta4-5alpha-reductase
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testosterone delta4-hydrogenase
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type 1 5alpha-reductase
type 1 5alphaR
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type 1 SR
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type 1 steroid 5alpha reductase
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type 2 5alpha-reductase
type 2 5alphaR
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type 2 SR
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type 2 steroid 5alpha reductase
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type II 5alpha-reductase
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type-1 5alpha-reductase
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type-2 5alpha-reductase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a 3-oxo-5alpha-steroid + NADP+ = a 3-oxo-DELTA4-steroid + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
3-oxo-5alpha-steroid:NADP+ DELTA4-oxidoreductase
The enzyme catalyses the conversion of assorted 3-oxo-Delta4 steroids into their corresponding 5alpha form. Substrates for the mammalian enzyme include testosterone, progesterone, and corticosterone. Substrates for the plant enzyme are brassinosteroids such as campest-4-en-3-one and (22alpha)-hydroxy-campest-4-en-3-one. cf. EC 1.3.99.5, 3-oxo-5alpha-steroid 4-dehydrogenase (acceptor).
CAS REGISTRY NUMBER
COMMENTARY hide
37255-34-8
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72412-84-1
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9029-09-8
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
11alpha-hydroxyprogesterone + NADPH + H+
11alpha-hydroxydihydroprogesterone + NADP+
show the reaction diagram
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-
-
?
11beta,17alpha-dihydroxyprogesterone + NADPH + H+
11beta,17alpha-hydroxydihydroprogesterone + NADP+
show the reaction diagram
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-
-
?
11beta-hydroxyprogesterone + NADPH + H+
11beta-hydroxydihydroprogesterone + NADP+
show the reaction diagram
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?
17alpha-hydroxyprogesterone + NADPH + H+
17alpha-hydroxy-5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
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?
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
show the reaction diagram
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?
3-keto-delta4-abiraterone + NADPH + H+
? + NADP+
show the reaction diagram
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?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
show the reaction diagram
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
show the reaction diagram
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?
corticosterone + NADPH + H+
5alpha-dihydrocorticosterone + NADP+
show the reaction diagram
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r
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
show the reaction diagram
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?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
show the reaction diagram
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
show the reaction diagram
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?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
show the reaction diagram
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
show the reaction diagram
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
additional information
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+/-)-LY191704
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i.e. (4aS,10aR)-7-chloro-1-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-2(1H)-one, non-steroidal, most potent benzoquinoline mimicing 4-azasteroid inhibitors, and specific for isozyme 5alphaR-1, IC50 is 30 nM
(10bR)-8-chloro-4,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
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isoform II, 49% inhibition at 0.02 mM
(10bR)-8-chloro-4,5,10b-trimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
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isoform II, 57% inhibition at 0.029 mM
(10bR)-8-chloro-5,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
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isoform II, 42% inhibition at 0.03 mM
(1E,4E,6E)-1,7-bis(3-hydroxy-4-methoxyphenyl)hepta-1,4,6-trien-3-one
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(1E,4E,6E)-1,7-bis(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
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(1E,4E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
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(1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
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(1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-one
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(1E,4E,6E)-1-(2-chlorophenyl)-7-phenylhepta-1,4,6-trien-3-one
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(1E,4E,6E)-1-(3-hydroxy-4-methoxyphenyl)-7-(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
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(1E,4E,6E)-1-(3-nitrophenyl)-7-phenylhepta-1,4,6-trien-3-one
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(1E,4E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
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(1E,4E,6E)-1-(4-methoxyphenyl)-7-phenylhepta-1,4,6-trien-3-one
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(1E,4E,6E)-7-(3-hydroxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
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(1E,4E,6E)-7-[3-(cycloprop-2-en-1-yloxy)phenyl]-1-(2-hydroxyphenyl)hepta-1,4,6-trien-3-one
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(1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione
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(2E)-3-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]prop-2-enamide
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(2E)-3-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
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(2E)-3-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-N-[2-(4-methoxyphenyl)ethyl]prop-2-enamide
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(4aS)-7-chloro-4a-methyl-2,3,4,4a-tetrahydrophenanthrene-2-carboxylic acid
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(4aS,10bS)-4,10b-dimethyl-8-[(E)-2-naphthylylvinyl]-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 6 nM, isoform II, 50% inhibition at 0.00134 mM
(4aS,10bS)-4,10b-dimethyl-8-[(E)-2-phenylvinyl]-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 6 nM, isoform II, 50% inhibition at 0.0014 mM
(4aS,10bS)-4,8-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 11 nM
(4aS,10bS)-8-(2-furyl)-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 59 nM, isoform II, 50% inhibition above 10 nM
(4aS,10bS)-8-bromo-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 35 nM
(4aS,10bS)-8-chloro-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 60 nM
(4aS,10bS)-8-chloro-4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 17 nM
(4aS,10bS)-8-chloro-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 8 nM, isoform II, 50% inhibition above 0.01 mM
(4aS,10bS)-8-fluoro-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 35 nM
(4aS,10bS)-8-methoxy-4-methyl-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
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isoform I, 50% inhibition at 120 nM
(4E,6E)-1-(4-hydroxyphenyl)-7-phenylhepta-4,6-dien-3-one
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(4R)-4,8-dimethyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
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isoform I, 50% inhibition at 312 nM
(4R)-8-chloro-4-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
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isoform I, 50% inhibition at 141 nM
(4S)-4,8-dimethyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
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isoform I, 50% inhibition at 137 nM
(6E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one
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(6R)-8-chloro-6-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
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isoform I, 50% inhibition at 188 nM
1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
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isoform I, 50% inhibition at 298 nM
1-methyl-5-(4-(2-phenylacetyl)phenyl)pyridin-2(1H)-one
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61% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
10-azasteroids
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several
17-diisopropylcarbamoyl-2-androsten-3-carboxylate
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17-diisopropylcarbamoyl-3,5-androstadien-3-carboxylate
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17-diisopropylcarbamoyl-3-androsten-3-carboxyate
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17-diisopropylcarbamoyl-androstan-3-carboxylate
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17-tert-butylcarbamoyl-3,5-androstadien-3-carbaldehyde
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17-tert-butylcarbamoyl-3,5-androstadien-3-carboxylate
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dead-end inhibition versus testosterone
17-tert-butylcarbamoyl-3,5-androstadien-3-ol
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17a-(2-propionoxyethyl)-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 100% inhibition; 0.01 mM, 8.5% inhibition
17a-allyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 0.4% inhibition; 0.01 mM, 99% inhibition
17a-ethyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 100% inhibition; 0.01 mM, 32.3% inhibition
17a-methyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
0.01 mM, 18.9% inhibition; 0.01 mM, 99% inhibition
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3 20-dione
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17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3,20-dione
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17alpha-phenylcarbamoyloxy-4-pregnen-3,20-dione
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17beta-(N-tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid
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17beta-Carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids
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formation of enzyme-NADP+-inhibitor complex
17beta[3-(N-4-bromophenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
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17beta[3-(N-4-chlorophenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
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17beta[3-(N-4-ethoxyphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
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17beta[3-(N-4-ethylphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
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17beta[3-(N-4-methoxyphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
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17beta[3-(N-4-phenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
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17beta[3-(N-4-tolyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
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slight inhibition
2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
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2,5-dihydroxy-1,4-benzoquinone
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inhibitor isolated from Thai mangrove Avicennia marina
-
2,6,4'-methoxybenzophenone
from Anemarrhena aspholoides rhizomes
2-(16-(acetylthio)hexadecanamido)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate
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43% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
2-(2-(16-(acetylthio)hexadecanamido)ethoxy)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate
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33% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
2-(2-hydroxypropan-2-yl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
-
inhibitor isolated from Thai mangrove Avicennia marina
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2-acetyl-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
-
inhibitor isolated from Thai mangrove Avicennia marina
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2-acetylnaphtho[2,3-b]furan-4,9-dione
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inhibitor isolated from Thai mangrove Avicennia marina
-
2-hydroxy-4-[(4E,6E)-3-oxo-7-phenylhepta-4,6-dien-1-yl]phenyl acetate
-
-
2-methoxy-5-[(6E)-3-methoxy-7-phenylhept-6-en-1-yl]benzene-1,4-diol
-
-
2-propanoylnaphtho[2,3-b]furan-4,9-dione
-
inhibitor isolated from Thai mangrove Avicennia marina
-
3-Androstene-3-carboxylic acids
-
-
3-keto-5alpha-abiraterone
-
-
3-keto-Delta4-abiraterone
-
-
3beta-(3'-oxapentanoyloxy)-androst-5-en-17-one
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
3beta-acetoxyandrost-5-en-17-one
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
3beta-hexanoyloxyandrost-5-en-17-one
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
4,6,8-trimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 15.8 nM
4,8-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 20 nM
4-(1-[4-[acetyl(methyl)amino]-3-methylphenyl]-1-ethylpropyl)-2-methylphenyl diethylcarbamate
-
22% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]-3-methylphenyl]-1-ethylpropyl)phenyl diethylcarbamate
-
25% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)-2-methylphenyl diethylcarbamate
-
56% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl 4-methylpiperazine-1-carboxylate
-
17% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl azepane-1-carboxylate
-
70% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl azocane-1-carboxylate
-
20% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl bis(1-methylethyl)carbamate
-
72% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl bis(1-methylpropyl)carbamate
-
22% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dibenzylcarbamate
-
51% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dibutylcarbamate
-
32% inhibition at 0.001 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl diethylcarbamate
-
57% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dimethylcarbamate
-
29% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl dipropylcarbamate
-
77% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl morpholine-4-carboxylate
-
15% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl piperidine-1-carboxylate
-
68% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-ethylpropyl)phenyl pyrrolidine-1-carboxylate
-
57% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-methylethyl)phenyl diethylcarbamate
-
16% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]-1-propylbutyl)phenyl diethylcarbamate
-
27% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]cyclobutyl)phenyl diethylcarbamate
-
16% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]cycloheptyl)phenyl diethylcarbamate
-
25% inhibition at 0.01 mM; 46% inhibition at 0.01 mM
4-(1-[4-[acetyl(methyl)amino]phenyl]cyclopentyl)phenyl diethylcarbamate
-
5% inhibition at 0.01 mM
4-(2-[5-[(diphenylmethyl)carbamoyl]-1-benzofuran-2-yl]phenoxy)butanoic acid
-
isoform I, 50% inhibition at 310 nM, isoform II, 50% inhibition above 0.1 mM
4-(2-[6-[(diphenylmethyl)carbamoyl]-1-benzofuran-2-yl]phenoxy)butanoic acid
-
isoform I, 50% inhibition at 62 nM, isoform II, 50% inhibition at 270 nM
4-(3-(4-(N-methylacetamido)phenyl)pentan-3-yl)phenyl dibenzylcarbamate
-
competitive inhibitor
4-(4'-formylphenoxy)benzoic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.007 mM
4-(biphenyl-4'-yloxy)phenylacetic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.00006 mM
4-(biphenyl-4'-yloxy)phenylformic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.000006 mM
4-(N-(diphenyl)acetyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0013 mM
4-(N-(diphenyl)carbamoyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37°C, DU145 cells, 10% inhibition at 0.01 mM, BPH tissue, 68% inhibition at 0.01 mM
4-(N-(tert-butyloxycarbonyl)-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37°C, DU145 cells, 2% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.0078 mM
4-(N-adamantanoyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37°C, DU145 cells, 7% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00043 mM
4-Androsten-3-one-17beta-carboxylic acid
-
competitive
4-azasteroids
4-carboxy-4'-(N,N-dicyclohexyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0047 mM, DU145 cells, 44% inhibition at 0.001 mM
4-carboxy-4'-(N,N-diisobutyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.004 mM, DU145 cells, 16% inhibition at 0.001 mM
4-carboxy-4'-(N,N-diisopropyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 15% inhibition at 0.001 mM, DU145 cells, 9% inhibition at 0.001 mM
4-carboxy-4'-(N,N-diphenyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.00233 mM, DU145 cells, 28% inhibition at 0.001 mM
4-carboxy-4'-(N-adamantyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0019 mM, DU145 cells, 16% inhibition at 0.001 mM
4-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 185 nM
4-methyl-4-azasteroids
-
4-methyl-5,6-dihydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 1400 nM
4-methyl-azasteroid
-
-
4-[(6E)-3-oxo-7-phenylhept-6-en-1-yl]phenyl acetate
-
-
4-[1-[4-(acetylamino)-3-methylphenyl]-1-ethylpropyl]-2-methylphenyl diethylcarbamate
-
17% inhibition at 0.01 mM
4-[2-(6-[[bis(4-fluorophenyl)methyl]carbamoyl]-1-benzofuran-2-yl)phenoxy]butanoic acid
-
isoform I, 50% inhibition at 50 nM, isoform II, 50% inhibition at 340 nM
4-[2-(6-[[bis(4-methoxyphenyl)methyl]amino]-1-benzofuran-2-yl)phenoxy]butanoic acid
-
isoform I, 50% inhibition at 42 nM, isoform II, 50% inhibition at 480 nM
4-[2-(6-[[bis(4-methoxyphenyl)methyl]carbamoyl]-1-benzofuran-2-yl)phenoxy]butanoic acid
-
isoform I, 50% inhibition at 130 nM, isoform II, 50% inhibition at 930 nM
4-[3-[(2,2-diphenyl-1,3-benzodioxol-5-yl)oxy]-2-methyl-1H-indol-1-yl]butanoic acid
-
isoform I, 50% inhibition at 10 nM, isoform II, 50% inhibition at 6300 nM
6,8-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 14.3 nM
6-azasteroids
-
several
7-bromo-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
-
7-chloro-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
-
8-bromo-4-methyl-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 60 nM, isoform I
8-chloro-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 49 nM
8-chloro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 460 nM, isoform I
8-chloro-1-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 204 nM
8-chloro-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 459 nM
8-chloro-4,5-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 15.6 nM
8-chloro-4,6-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 8.5 nM
8-chloro-4-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 7.6 nM
8-chloro-4-methyl-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 30 nM, isoform I
8-chloro-5-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 346 nM
8-chloro-6-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 14.4 nM
8-fluoro-1,4,5,6-tetrahydrobenzo[f]quinolin-3(2H)-one
-
50% inhibition at 600 nM, isoform I
8-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 376 nM
8-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 176 nM
acrylate episteride
-
-
alpha-4-azasteroids
-
substitution of finasteride N-group by 6-azasteroids increased the rate of inhibition of type-1 5-alpha-reductases
avicequinone C
-
inhibitor isolated from Thai mangrove Avicennia marina
-
benzoquilizin-3-ones
-
diverse, mimics of 10-azasteroids, overview, structure-activity relationships
benzoquinolines
-
compounds as mimics of 4-azasteroid inhibitors, diverse, overview, compounds derived from 6-azasteroids, overview
bisdemethoxycurcumin
-
22.2% inhibition at 0.3 mM
cis-hinokiresinol
from Anemarrhena aspholoides rhizomes
curcumin
-
complete inhibition at 0.3 mM
dehydroepiandrosterone
-
good in vitro inhibitory activity, but compound does not bind to the androgen receptors
demethoxycurcumin
-
complete inhibition at 0.3 mM
deoxycorticosterone acetate
-
competitive
docosanol
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
dutasteride
epristeride
-
-
estradiol
-
in female genital skin fibroblasts
estradiol-17beta
-
-
finasteride
FK143
-
i.e. 4-[3-(3-[[bis-(4-isobutyl-phenyl)-methyl]amino]-benzoyl)-indol-1-yl]-butyric acid, a non-steroidal bi-substrate inhibitor
Lapachol
-
inhibitor isolated from Thai mangrove Avicennia marina
lauric acid
-
isoform 1, 50% inhibition at 0.0167 mM, isoform 2, 50% inhibition at 0.0186 mM
lauric acid ethyl ester
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
Lawsone
-
inhibitor isolated from Thai mangrove Avicennia marina
linoleic acid
-
isoform 1, 50% inhibition at 0.013 mM, isoform 2, 50% inhibition at 0.035 mM
LY306089
-
a non steroid, non-competitive inhibitor of type I 5alpha-reductase in DU145 cells
mangiferin
a 1,3,6,7-tetrahydroxyxanthone-C2-beta-D-glucoside, from Anemarrhena aspholoides rhizomes, directly inhibits SRD5A2 binding to a complex of enzyme and substrate
MK386
myristic acid
-
isoform 2, 50% inhibition at 0.004 mM
N,N-bis(1-methylethyl)-4-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yl)benzamide
-
isoform I, 50% inhibition at 510 nM, isoform II, 9% inhibition at 0.01 mM
N,N-dicyclohexyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0067 mM, DU145 cells, 4% inhibition at 0.001 mM
N,N-diisobutyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 46% inhibition at 0.01 mM
N,N-diisopropyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide
-
8% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
N,N-diisopropyl-2-(4-(1-methyl-6-oxopiperidin-3-yl)phenoxy)acetamide
-
6% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
N,N-diisopropyl-2-(4-(2-methyl-4-oxo-3,4-dihydropyridin-1(2H)-yl)phenoxy)acetamide
-
3% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
N,N-diisopropyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 36% inhibition at 0.01 mM, DU145 cells, 4% inhibition at 0.001 mM
N,N-diphenyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.00085 mM
N-(1-adamantanoyl)piperdine-4-(2-methoxybenzyliden-4-carboxylic acid)
-
pH 5.5, 37°C, DU145 cells, 10% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.0012 mM
N-(1-adamantanoyl)piperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
pH 5.5, 37°C, DU145 cells, 20% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00021 mM
N-(3,3-diphenyl)propanoylpiperidine-4-(benzylidene-4-carboxylic acid)
-
pH 5.5, 37°C, DU145 cells, 8% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.0011 mM
N-(dicyclohexyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
pH 5.5, 37°C, DU145 cells, 12% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.000011 mM
N-(dicyclohexyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)
-
pH 5.5, 37°C, DU145 cells, 5% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00013 mM
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-3-carboxylic acid)
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0007mM
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-acetic acid)
-
pH 5.5, 37°C, DU145 cells, 6% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.000006 mM
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-carboxylic acid)
-
pH 5.5, 37°C, DU145 cells, 46% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00006 mM
N-(diphenyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
pH 5.5, 37°C, DU145 cells, 2% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.00041 mM
N-(diphenyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)
-
pH 5.5, 37°C, DU145 cells, 8% inhibition at 0.01 mM, BPH tissue, 50% inhibition at 0.0035 mM
N-(diphenyl)acetylpiperidine-4-(benzylidene-3-carboxylic acid)
-
pH 5.5, 37°C, DU145 cells, 6% inhibition at 0.01 mM, BPH tissue, 57% inhibition at 0.01 mM
N-(diphenyl)acetylpiperidine-4-(benzylidene-4-acetic acid)
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.000075 mM
N-adamantyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.00038 mM
N-allyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide
-
6% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
N-allyl-2-(4-(2-methyl-4-oxo-3,4-dihydropyridin-1(2H)-yl)phenoxy)acetamide
-
8% inhibition of type 1 steroid 5alpha reductase at 0.01 mM and 12% inhibition of type 2 steroid 5alpha reductase at 0.01 mM
N-cyclohexyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0023 mM
N-phenyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.001 mM
N-tert-butyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0028 mM
naphtho[2,3-b]furan-4,9-dione
-
inhibitor isolated from Thai mangrove Avicennia marina
non-steroidal bi-substrate inhibitors
-
several, structures, overview
-
oleic acid
-
isoform 1, 50% inhibition at 0.004 mM, isoform 2, 50% inhibition above 0.1 mM
oleic acid ethyl ester
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
ONO 3805
-
-
ONO-3805
-
a non-steroidal bi-substrate inhibitor
palmitic acid
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
penta-O-galloyl-beta-D-glucose
-
from Thea sativa, inhibits the expression of androgen receptor and reduce secretion of prostate-specific antigen in LNCaP prostate cancer cells
progesterone
-
competitive
sitosterol
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
SKF105657
-
a steroidal type II 5alpha-reductase specific inhibitor
stearic acid
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
steroid carboxylic acid compounds
-
diverse, tricyclic aryl acid mimics of, overview
theaflavin-3,3'-digallate
-
from Thea sativa, inhibits the expression of androgen receptor and reduce secretion of prostate-specific antigen in LNCaP prostate cancer cells
tocopherol
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
turosteride
-
-
Unsaturated 3-carboxysteroids
-
-
-
Zn2+
-
0.1 mM ZnCl2
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
androstandione
-
in male foreskin fibroblasts
androstenedione
-
in male foreskin fibroblasts
Oxytocin
-
increases activity in human prostate epithelial cells
testosterone
-
in female genital skin fibroblasts
additional information
-
oxytocin does not stimulate enzyme activity or expression in human prostate epithelial cells
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0061 - 0.0088
17alpha-hydroxyprogesterone
0.0002 - 0.0004
20alpha-hydroxyprogesterone
0.003
3-keto-Delta4-abiraterone
pH 7.4, 37°C
-
0.0008 - 0.0031
androstenedione
0.004 - 0.018
corticosterone
0.011 - 0.65
NADPH
0.0001 - 0.00069
progesterone
0.0000013 - 0.0156
testosterone
additional information
additional information
-
variations of Km with various concentrations of zearaleone, zearalanol or estradiol-17beta
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000006
(+)-LY191704
-
-
0.000004
(-)-LY191704
-
-
0.00092
(10bR)-8-chloro-4,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform I
0.0011
(10bR)-8-chloro-4,5,10b-trimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform I
0.00026 - 0.0012
(4aS)-7-chloro-4a-methyl-2,3,4,4a-tetrahydrophenanthrene-2-carboxylic acid
0.000085
17-diisopropylcarbamoyl-2-androsten-3-carboxylate
-
-
0.000007 - 0.000018
17-diisopropylcarbamoyl-3,5-androstadien-3-carboxylate
-
-
0.00003
17-diisopropylcarbamoyl-3-androsten-3-carboxyate
-
-
0.0022
17-diisopropylcarbamoyl-androstan-3-carboxylate
-
-
0.0045
17-tert-butylcarbamoyl-3,5-androstadien-3-carbaldehyde
-
-
0.000033
17-tert-butylcarbamoyl-3,5-androstadien-3-carboxylate
-
-
0.0042
17-tert-butylcarbamoyl-3,5-androstadien-3-ol
-
-
0.000036 - 0.0093
17beta-(N-tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid
0.000315 - 0.01
2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
0.0000058
4,8-dimethyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I
0.000003 - 0.000004
4-methyl-azasteroid
0.000026 - 0.01
7-bromo-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
0.00032 - 0.0025
7-chloro-2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
0.0000027
8-chloro-4-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I
0.0000003 - 0.0041
acylate episteride
-
0.0000043 - 0.000017
dutasteride
0.000001 - 0.005
finasteride
0.000004
LY306089
-
-
additional information
additional information
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00003
(+/-)-LY191704
Homo sapiens
-
i.e. (4aS,10aR)-7-chloro-1-methyl-3,4,4a,9,10,10a-hexahydrophenanthren-2(1H)-one, non-steroidal, most potent benzoquinoline mimicing 4-azasteroid inhibitors, and specific for isozyme 5alphaR-1, IC50 is 30 nM
0.00892
(1E,4E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
Homo sapiens
-
at pH 7.4 and 37°C
0.0935
(1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
Homo sapiens
-
at pH 7.4 and 37°C
0.0788
(1E,4E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
Homo sapiens
-
at pH 7.4 and 37°C
0.0886
(1E,4E,6E)-7-(3-hydroxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
Homo sapiens
-
at pH 7.4 and 37°C
0.0153
(1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione
Homo sapiens
-
at pH 7.4 and 37°C
0.000026
17a-(2-propionoxyethyl)-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
Homo sapiens
pH not specified in the publication, 37°C
0.000073
17a-allyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
Homo sapiens
pH not specified in the publication, 37°C
0.000022
17a-ethyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
Homo sapiens
pH not specified in the publication, 37°C
0.000054
17a-methyl-17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acid
Homo sapiens
pH not specified in the publication, 37°C
0.00005
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3 20-dione
Homo sapiens
-
in the presence of 1 mM dithiothreitol, in 40 mM sodium phosphate buffer, at pH 6.5
0.00005
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3,20-dione
Homo sapiens
-
with 1 mM dithiothreitol in 40 mM sodium phosphate buffer, at pH 6.5 and 37°C
0.00001
17alpha-phenylcarbamoyloxy-4-pregnen-3,20-dione
0.2
2,5-dihydroxy-1,4-benzoquinone
Homo sapiens
-
cell-based assay, 37°C, pH not specified in the publication
-
0.0096
2-(2-hydroxypropan-2-yl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
Homo sapiens
-
cell-based assay, 37°C, pH not specified in the publication
-
0.0012
2-acetyl-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
Homo sapiens
-
cell-based assay, 37°C, pH not specified in the publication
-
0.0002
2-propanoylnaphtho[2,3-b]furan-4,9-dione
Homo sapiens
-
cell-based assay, 37°C, pH not specified in the publication
-
0.0000011
3beta-(3'-oxapentanoyloxy)-androst-5-en-17-one
Homo sapiens
-
pH 6.5, 37°C
0.0000052
3beta-acetoxyandrost-5-en-17-one
Homo sapiens
-
pH 6.5, 37°C
0.000000002
3beta-hexanoyloxyandrost-5-en-17-one
Homo sapiens
-
pH 6.5, 37°C
0.00084
4-(3-(4-(N-methylacetamido)phenyl)pentan-3-yl)phenyl dibenzylcarbamate
Homo sapiens
-
-
0.0045
avicequinone C
Homo sapiens
-
cell-based assay, 37°C, pH not specified in the publication
-
0.3
bisdemethoxycurcumin
Homo sapiens
-
at pH 7.4 and 37°C
0.0134
curcumin
Homo sapiens
-
at pH 7.4 and 37°C
0.000025
dehydroepiandrosterone
Homo sapiens
-
pH 6.5, 37°C
0.0225
demethoxycurcumin
Homo sapiens
-
at pH 7.4 and 37°C
0.0000085 - 0.008
finasteride
0.2
Lapachol
Homo sapiens
-
cell-based assay, 37°C, pH not specified in the publication
0.2
Lawsone
Homo sapiens
-
cell-based assay, 37°C, pH not specified in the publication
0.0005
MK386
Homo sapiens
-
-
0.0043
naphtho[2,3-b]furan-4,9-dione
Homo sapiens
-
cell-based assay, 37°C, pH not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
significant differences in 5 alpha-R2 activity levels between the cancerous and non-cancerous groups are observed
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.2 - 5.6
-
mutant G34R
6 - 6.5
-
mutant P181L
6.2
-
female
6.5
-
assay at
7 - 9
-
human: 2 forms, 1. pH-optimum 5.5 (only in fibroblasts derived from genital skin), 2. pH-optimum 7-9 (in both genital and nongenital skin regions and in fibroblast from all skin regions)
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 9
-
recombinant human 5alpha-reductase isozyme 1
4.5 - 9.5
-
recombinant human 5alpha-reductase isozyme 2
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
from beard and axillary hair and frontal scalp hair
Manually annotated by BRENDA team
-
the enzyme is detected in biopsies of pelvic endometriosis
Manually annotated by BRENDA team
-
both type 1 and type 2 isoenzyme, copy number of mRNA and activity of type 1 isoenzyme is significantly higher than type 2
Manually annotated by BRENDA team
-
type 2 isoenzyme
Manually annotated by BRENDA team
additional information
-
isozymes show different tissue distribution in androgen target organs
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
additional information
mutations of the SRD5A2 gene, e.g. Leu55Gln, cause 5alpha-reductase type 2 deficiency and masculinization defects of varying degree as a result of a prenatal lack of 5alpha-dihydrotestosterone to predominantly female phenotype newborn patient, detailed overview
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
S5A1_HUMAN
259
4
29459
Swiss-Prot
other Location (Reliability: 5)
S5A2_HUMAN
254
6
28393
Swiss-Prot
Secretory Pathway (Reliability: 3)
PORED_HUMAN
318
6
36521
Swiss-Prot
Secretory Pathway (Reliability: 3)
A0A7P0T816_HUMAN
236
4
26588
TrEMBL
Secretory Pathway (Reliability: 3)
H0Y9P9_HUMAN
182
3
21036
TrEMBL
Secretory Pathway (Reliability: 1)
A0A7P0TBH6_HUMAN
273
5
31217
TrEMBL
Secretory Pathway (Reliability: 3)
A0A7P0T9P9_HUMAN
284
5
31861
TrEMBL
Secretory Pathway (Reliability: 3)
A0A7P0T9J3_HUMAN
175
2
19982
TrEMBL
Secretory Pathway (Reliability: 3)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
24000
-
5alphaR2, immunoblotting
26000
-
5alphaR1, SDS-PAGE
42000
-
5alpha-reductase isoenzyme 2, SDS-PAGE, after treatment with O-glycosidase and neuraminidase a protein of an apparent molecular weight of 30 kDa appears
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
molecular docking of inhibitors. The furanonaphthoquinones reside closely adjacent to NADPH and likely interact with Tyr95 of the enzyme as well as NADPH
-
structure of SRD5A2 with finasteride at 2.8 A, reveals a 7-TM structural topology and an intermediate adduct of finasteride and NADPH as NADP-dihydrofinasteride in a largely enclosed binding cavity inside the transmembrane domain. The molecular mechanisms of the reaction and of finasteride inhibition involve residues E57 and Y91. The cytosolic region that regulates NADPH/NADP+ exchange displays high conformational dynamics
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A207D
-
the mutation is associated with 5alpha-reductase type 2 deficiency
A248V
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
A51T
-
constitutional variant, reduction of the apparent Ki for both finasteride and dutasteride
C133G
-
the mutation is associated with 5alpha-reductase type 2 deficiency
C5R
-
constitutional variant, reduction of the apparent Ki for both finasteride and dutasteride
F118L
-
somatic variant, no significant change of the apparent Ki for both finasteride and dutasteride
F194L
-
constitutional variant, time-independent inhibition, displays lower apparent Ki for finasteride than dutasteride
F234L
-
constitutional variant, reduction of the apparent Ki for finasteride but not for dutasteride
G183D
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
G183S
-
mutant of 5alpha-reductase isozyme type-2
G191E
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
G196S
G34R
-
mutant of 5alpha-reductase isozyme type-2
G34W
-
the mutation is associated with 5alpha-reductase type 2 deficiency
H231R
-
mutant of 5alpha-reductase isozyme type-2
H264Q
-
mutant of 5alpha-reductase isozyme type-2
L221P
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
L226P
-
somatic variant, reduction of the apparent Ki for finasteride but not for dutasteride
L55Q
the naturally occuring homozygote point mutation causes SRD5A2 deficiency and leads to leading to an impaired conversion of testosterone to 5alpha-dihydrotestosterone, and thus to predominantly female phenotype at 3 days of age with ambiguous external genitalia: testes palpable in the extended labia resembling a scrotum bipartitum, micropenis with hypospadias and lack of an introitus vaginae but a perineal dimple in accordance with steroid 5alpha-reductase deficiency type III
N193S
-
mutant of 5alpha-reductase isozyme type-2
P181L
-
mutant of 5alpha-reductase isozyme type-2
P30L
-
constitutional variant, more than 100fold lower apparent Ki for dutasteride than for finasteride
P48R
-
constitutional variant, displays lower apparent Ki for finasteride than dutasteride in the 10 min reaction
R145W
-
mutant of 5alpha-reductase isozyme type-2
R171S
-
mutant of 5alpha-reductase isozyme type-2
R227Q
-
constitutional variant, reduction of the apparent Ki for both finasteride and dutasteride
R246W
-
mutant of 5alpha-reductase isozyme type-2
T187M
-
constitutional variant, reduction of the apparent Ki for both finasteride and dutasteride
V189A
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
V3I
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
V63M
-
somatic variant, reduction of the apparent Ki for both finasteride and dutasteride
W53X
-
the mutation is associated with 5alpha-reductase type 2 deficiency
Y235F
-
the mutation is associated with 5alpha-reductase type 2 deficiency
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
0.5% n-octyl beta-D-glucopyranoside stabilizes
-
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
5alpha-reductase 2 purified using a four-step chromatographic procedure
-
recombinant His-tagged SRD5A2 from CHO cells by nickel affinity chromatography and anion exchange chromatography
recombinant protein, use of detergents Triton X-100 and Nonidet P-40 for solubilization
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in HEK-293 cell
expression in Sf9 cell
expression of polyhistidine-tagged, codon-optimized cDNA in Escherichia coli
gene SRD5A2, DNA and amino acid sequence determination, expression of His-tagged enzyme in Escherichia coli strain DH5alpha and in CHO cells
into pCMV7 and transfered to COS-1 cells
-
recombinant expression of isozymes 5alphaR-1 and 5alphaR-2 in e.g. human DU145 cells, in COS-1 cells, and in CHO 1827 and CHO 1829 cells, isozymes are chromosomal differently localized
-
transfection of HEK-293 cell
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
androgen regulates the mRNA level of 5alpha reductase isoenzymes in a cell type-specific manner. Regulation occurs at the transcriptional level, and the androgen receptor is necessary for this regulation
androgen regulates the mRNA level of 5alpha reductase isoenzymes in a cell type-specific manner. Regulation occurs at the transcriptional level, and the androgen receptor is necessary for this regulation. The androgen receptor is recruited to a negative androgen response element on the promoter of isoform SRD5A3 in vivo and directly binds to the negative androgen response element in vitro
RENATURED/Commentary
ORGANISM
UNIPROT
LITERATURE
functional reconstitution of recombinant enzyme, incorporation of the purified isoenzymes into Triton X-100-saturated dioleoylphosphatidylcholine liposomes and removal of excess detergent with polystyrene beads
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
pharmacology
-
enzyme is a target for drug developement
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Holt, D.A.; Levy, M.A.; Oh, H.J.; Erb, J.M.; Heaslip, J.I.; Brandt, M.; Lan-Hargest, H.Y.; Metcalf, B.W.
Inhibition of steroid 5alpha-reductase by unsaturated 3-carboxysteroids
J. Med. Chem.
33
943-950
1990
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Holt, D.A.; Levy, M.A.; Ladd, D.L.; Oh, H.J.; Erb, J.M.; Heaslip, J.I.; Brandt, M.; Metcalf, B.M.
Steroidal A ring aryl carboxylic acids: a new class of steroid 5alpha-reductase inhibitors
J. Med. Chem.
33
937-942
1990
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Metcalf, B.W.; Holt, D.A.; Levy, M.A.; Erb, J.M.; Heaslip, J.I.; Brandt, M.; Oh, H.J.
Potent inhibition of human steroid 5alpha-reductase (EC 1.3.1.30) by 3-androstene-3-carboxylic acids
Bioorg. Chem.
17
372-376
1989
Homo sapiens
-
Manually annotated by BRENDA team
Graef, V.; Golf, S.W.; Tuschen, M.
NADPH: 4-ene-3-oxosteroid-5alpha-reductase and NADH: 4-ene-3-oxosteroid-5alpha-reductase in liver microsomes of different species of animals
J. Steroid Biochem.
14
883-887
1981
Gallus gallus, Chinchilla chinchilla, Oryctolagus cuniculus, Homo sapiens, Mesocricetus auratus, Mus musculus, Rattus norvegicus, Sus scrofa
Manually annotated by BRENDA team
Thouvenot, D.; Morfin, R.F.
Interferences of zearalenone, zearalanol or estradiol-17beta with the steroid-metabolizing enzymes of the human prostate gland
J. Steroid Biochem.
13
1337-1345
1980
Homo sapiens
Manually annotated by BRENDA team
Voigt, W.; Hsia, S.I.
Further studies on testosterone 5 -reductase of human skin. Structural features of steroid inhibitors
J. Biol. Chem.
248
4280-4285
1973
Homo sapiens
Manually annotated by BRENDA team
Moore, R.J.; Wilson, J.D.
Steroid 5alpha-reductase in cultured human fibroblasts. Biochemical and genetic evidence for two distinct enzyme activities
J. Biol. Chem.
251
5895-5900
1976
Homo sapiens
Manually annotated by BRENDA team
Wallace, A.M.; Grant, J.K.
Effect of zinc on androgen metabolism in the human hyperplastic prostate
Biochem. Soc. Trans.
3
540-542
1975
Homo sapiens
Manually annotated by BRENDA team
Cowan, R.A.; Cook, B.; Cowan, S.K.; Grant, J.K.; Sirett, D.A.N.; Wallace, A.M.
Testosterone 5alpha-reductase and the accumulation of dihydrotestosterone in benign prostatic hyperplasia
J. Steroid Biochem.
11
609-613
1979
Homo sapiens
Manually annotated by BRENDA team
Tian, G.; Mook, R.; Moss, M.L.; Frye, S.V.
Mechanism of time-dependent inhibition of 5alpha-reductases by delta 1-4-azasteroids: Toward perfection of rates of time-dependent inhibition by using ligand-binding energies
Biochemistry
34
13453-13459
1995
Homo sapiens
Manually annotated by BRENDA team
Wigley, W.C.; Prihoda, J.S.; Mowszowicz, I.; Mendonca, B.B.; New, M.I.; Wilson, J.D.; Russel, D.W.
Natural mutagenesis study of the human steroid 5alpha-reductase 2 isozyme
Biochemistry
33
1265-1270
1994
Homo sapiens
Manually annotated by BRENDA team
Quemener, E.; Amet, Y.; Fournier, G.; Di Stefano, S.; Abalain, J.H.; Floch, H.H.
Glyosylated nature of testosterone 5alpha-reductase 2 purified from human prostate
Biochem. Biophys. Res. Commun.
205
296-274
1994
Homo sapiens
-
Manually annotated by BRENDA team
Delos, S.; Iehle, C.; Martin, M.; Raynaud, J.P.
Inhibition of the activity of basic 5alpha-reductase (type 1) detected in DU 145 cells and expressed in insect cells
J. Steroid Biochem. Mol. Biol.
48
347-352
1994
Homo sapiens, Spodoptera frugiperda
Manually annotated by BRENDA team
Levy, M.A.; Brandt, M.; Sheedy, K.M.; Holt, D.A.; Heaslip, J.I.; Trill, J.J.; Ryan, P.J.; Morris, R.A.; Garrison, L.M.; Bergsma, D.J.
Cloning, expression and functional characterization of type 1 and type 2 steroid 5alpha-reductase from cynomolgus monkey: comparison with human and rat isoenzymes
J. Steroid Biochem. Mol. Biol.
52
307-319
1995
Homo sapiens, Macaca fascicularis, Rattus norvegicus
Manually annotated by BRENDA team
Beckmann, M.W.; Wieacker, P.; Dereser, M.M.; Flecken, U.; Breckwoldt, M.
Influence of steroid hormones on 5alpha-reductase activity in female and male genital skin fibroblats in culture
Acta Endocrinol.
128
161-167
1993
Homo sapiens
Manually annotated by BRENDA team
Cooke, G.M.; Pothier, F.; Murphy, B.D.
The effects of progesterone, 4,16-androstadien-3-one and MK-434 on the kinetics of pig testis microsomal testosterone-4-ene 5alpha-reductase activity
J. Steroid Biochem. Mol. Biol.
60
353-359
1997
Homo sapiens, Sus scrofa
Manually annotated by BRENDA team
Kaefer, M.; Audia, J.E.; Bruchovsky, N.; Goode, R.L.; Hsiao, K.C.; Leibovitch, I.Y.; Krushinski, J.H.; Lee, C; Steidle, C.P.; et al.
Charaterization of type I 5alpha-reductase activity in DU145 human prostatic adenocarcinoma cells
J. Steroid Biochem. Mol. Biol.
58
195-205
1996
Homo sapiens
Manually annotated by BRENDA team
Baxter, F.O.; Trivic, S.; Lee, I.R.
Structure-function studies of human 5alpha-reductase type 2 using site directed mutagenesis
J. Steroid Biochem. Mol. Biol.
77
167-175
2001
Homo sapiens
Manually annotated by BRENDA team
Lee, H.H.; Ho, C.T.; Lin, J.K.
Theaflavin-3,3'-digallate and penta-O-galloyl-beta-D-glucose inhibit rat liver microsomal 5alpha-reductase activity and the expression of androgen receptor in LNCaP prostate cancer cells
Carcinogenesis
25
1109-1118
2004
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Picard, F.; Hartmann, R.W.
N-Substituted 4-(4-carboxyphenoxy)benzamides.: Synthesis and evaluation as inhibitors of steroid 5alpha-reductase type 1 and 2
J. Enzyme Inhib. Med. Chem.
17
187-196
2002
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Picard, F.; Barassin, S.; Mokhtarian, A.; Hartmann, R.W.
Synthesis and evaluation of 2'-substituted 4-(4'-carboxy- or 4'-carboxymethylbenzylidene)-N-acylpiperidines: highly potent and in vivo active steroid 5alpha-reductase type 2 inhibitors
J. Med. Chem.
45
3406-3417
2002
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Raynaud, J.P.; Cousse, H.; Martin, P.M.
Inhibition of type 1 and type 2 5alpha-reductase activity by free fatty acids, active ingredients of Permixon
J. Steroid Biochem. Mol. Biol.
82
233-239
2002
Homo sapiens
Manually annotated by BRENDA team
Occhiato, E.G.; Guarna, A.; Danza, G.; Serio, M.
Selective non-steroidal inhibitors of 5alpha-reductase type 1
J. Steroid Biochem. Mol. Biol.
88
1-16
2004
Homo sapiens
Manually annotated by BRENDA team
Ranjan, M.; Diffley, P.; Stephen, G.; Price, D.; Walton, T.J.; Newton, R.P.
Comparative study of human steroid 5alpha-reductase isoforms in prostate and female breast skin tissues: sensitivity to inhibition by finasteride and epristeride
Life Sci.
71
115-126
2002
Homo sapiens
Manually annotated by BRENDA team
Shirakawa, T.; Okada, H.; Acharya, B.; Zhang, Z.; Hinata, N.; Wada, Y.; Uji, T.; Kamidono, S.; Gotoh, A.
Messenger RNA levels and enzyme activities of 5alpha-reductase types 1 and 2 in human benign prostatic hyperplasia (BPH) tissue
Prostate
58
33-40
2004
Homo sapiens
Manually annotated by BRENDA team
Woelfling, J.; Hackler, L.; Mernyak, E.; Schneider, G.; Toth, I.; Szecsi, M.; Julesz, J.; Sohar, P.; Csampai, A.
Neighboring group participation. Part 15. Stereoselective synthesis of some steroidal tetrahydrooxazin-2-ones, as novel presumed inhibitors of human 5alpha-reductase
Steroids
69
451-460
2004
Homo sapiens
Manually annotated by BRENDA team
Goodarzi, M.O.; Shah, N.A.; Antoine, H.J.; Pall, M.; Guo, X.; Azziz, R.
Variants in the 5alpha-reductase type 1 and type 2 genes are associated with polycystic ovary syndrome and the severity of hirsutism in affected women
J. Clin. Endocrinol. Metab.
91
4085-4091
2006
Homo sapiens
Manually annotated by BRENDA team
Makridakis, N.; Reichardt, J.K.
Pharmacogenetic analysis of human steroid 5alpha reductase type II: Comparison of finasteride and dutasteride
J. Mol. Endocrinol.
34
617-623
2005
Homo sapiens
Manually annotated by BRENDA team
Thomas, L.N.; Lazier, C.B.; Gupta, R.; Norman, R.W.; Troyer, D.A.; OBrien, S.P.; Rittmaster, R.S.
Differential alterations in 5alpha-reductase type 1 and type 2 levels during development and progression of prostate cancer
Prostate
63
231-239
2005
Homo sapiens
Manually annotated by BRENDA team
Rittmaster, R.S.
5alpha-reductase inhibitors in benign prostatic hyperplasia and prostate cancer risk reduction
Best Pract. Res. Clin. Endocrinol. Metab.
22
389-402
2008
Homo sapiens
Manually annotated by BRENDA team
Liu, S.; Yamauchi, H.
Different patterns of 5alpha-reductase expression, cellular distribution, and testosterone metabolism in human follicular dermal papilla cells
Biochem. Biophys. Res. Commun.
368
858-864
2008
Homo sapiens
Manually annotated by BRENDA team
McCarthy, A.R.; Hartmann, R.W.; Abell, A.D.
Evaluation of 4-substituted bicyclic pyridones as non-steroidal inhibitors of steroid 5alpha-reductase
Bioorg. Med. Chem. Lett.
17
3603-3607
2007
Homo sapiens
Manually annotated by BRENDA team
Hosoda, S.; Hashimoto, Y.
3,3-diphenylpentane skeleton as a steroid skeleton substitute: novel inhibitors of human 5alpha-reductase 1
Bioorg. Med. Chem. Lett.
17
5414-5418
2007
Homo sapiens
Manually annotated by BRENDA team
Carneiro, M.M.; Morsch, D.M.; Camargos, A.F.; Reis, F.M.; Spritzer, P.M.
Androgen receptor and 5alpha-reductase are expressed in pelvic endometriosis
BJOG
115
113-117
2008
Homo sapiens
Manually annotated by BRENDA team
Appell, R.A.
Male lower urinary tract symptoms: treatment with alpha-blockers, 5-alpha-reductase inhibitors, antimuscarinics, or a combination
Curr. Urol. Rep.
8
370-372
2007
Homo sapiens
Manually annotated by BRENDA team
Onen, I.H.; Ekmekci, A.; Eroglu, M.; Polat, F.; Biri, H.
The association of 5alpha-reductase II (SRD5A2) and 17 hydroxylase (CYP17) gene polymorphisms with prostate cancer patients in the Turkish population
DNA Cell Biol.
26
100-107
2007
Homo sapiens
Manually annotated by BRENDA team
Cussenot, O.; Azzouzi, A.R.; Nicolaiew, N.; Mangin, P.; Cormier, L.; Fournier, G.; Valeri, A.; Cancel-Tassin, G.
Low-activity V89L variant in SRD5A2 is associated with aggressive prostate cancer risk: an explanation for the adverse effects observed in chemoprevention trials using 5-alpha-reductase inhibitors
Eur. Urol.
52
1082-1087
2007
Homo sapiens
Manually annotated by BRENDA team
Baldinotti, F.; Majore, S.; Fogli, A.; Marrocco, G.; Ghirri, P.; Vuerich, M.; Tumini, S.; Boscherini, B.; Vetri, M.; Scommegna, S.; Rinaldi, R.; Simi, P.; Grammatico, P.
Molecular characterization of 6 unrelated Italian patients with 5alpha-reductase type 2 deficiency
J. Androl.
29
20-28
2008
Homo sapiens
Manually annotated by BRENDA team
Amory, J.K.; Wang, C.; Swerdloff, R.S.; Anawalt, B.D.; Matsumoto, A.M.; Bremner, W.J.; Walker, S.E.; Haberer, L.J.; Clark, R.V.
The effect of 5alpha-reductase inhibition with dutasteride and finasteride on semen parameters and serum hormones in healthy men
J. Clin. Endocrinol. Metab.
92
1659-1665
2007
Homo sapiens
Manually annotated by BRENDA team
Bratoeff, E.; Sainz, T.; Cabeza, M.; Heuze, I.; Recillas, S.; Perez, V.; Rodriguez, C.; Segura, T.; Gonzales, J.; Ramirez, E.
Steroids with a carbamate function at C-17, a novel class of inhibitors for human and hamster steroid 5alpha-reductase
J. Steroid Biochem. Mol. Biol.
107
48-56
2007
Homo sapiens, Mesocricetus auratus
Manually annotated by BRENDA team
Serfling, R.; Shulman, M.; Thompson, G.L.; Xiao, Z.; Benaim, E.; Roehrborn, C.G.; Rittmaster, R.
Quantifying the impact of prostate volumes, number of biopsy cores and 5alpha-reductase inhibitor therapy on the probability of prostate cancer detection using mathematical modeling
J. Urol.
177
2352-2356
2007
Homo sapiens
Manually annotated by BRENDA team
Tindall, D.J.; Rittmaster, R.S.
The rationale for inhibiting 5alpha-reductase isoenzymes in the prevention and treatment of prostate cancer
J. Urol.
179
1235-1242
2008
Homo sapiens, Rattus norvegicus
Manually annotated by BRENDA team
Amory, J.K.; Anawalt, B.D.; Matsumoto, A.M.; Page, S.T.; Bremner, W.J.; Wang, C.; Swerdloff, R.S.; Clark, R.V.
The effect of 5alpha-reductase inhibition with dutasteride and finasteride on bone mineral density, serum lipoproteins, hemoglobin, prostate specific antigen and sexual function in healthy young men
J. Urol.
179
2333-2338
2008
Homo sapiens
Manually annotated by BRENDA team
Assinder, S.J.
Oxytocin increases 5alpha -reductase activity of human prostate epithelial cells, but not stromal cells
Prostate
68
115-121
2008
Homo sapiens
Manually annotated by BRENDA team
Thevis, M.; Geyer, H.; Mareck, U.; Flenker, U.; Schaenzer, W.
Doping-control analysis of the 5alpha-reductase inhibitor finasteride: determination of its influence on urinary steroid profiles and detection of its major urinary metabolite
Ther. Drug Monit.
29
236-247
2007
Homo sapiens
Manually annotated by BRENDA team
Oliveira, O.L.; Koff, W.J.; Muraro, F.; Santos, E.B.; Gomes Soares, D.F.; Trindade, V.M.
Steroid 5-alpha reductase type 2 activity in biopsies from malignant and normal prostatic tissues
Clin. Chim. Acta
391
36-40
2008
Homo sapiens
Manually annotated by BRENDA team
Signorelli, S.S.; Barresi, V.; Musso, N.; Anzaldi, M.; Croce, E.; Fiore, V.; Condorelli, D.F.
Polymorphisms of steroid 5-alpha-reductase type I (SRD5A1) gene are associated to peripheral arterial disease
J. Endocrinol. Invest.
31
1092-1097
2008
Homo sapiens (P18405), Homo sapiens (P31213), Homo sapiens
Manually annotated by BRENDA team
Walter, K.N.; Kienzle, F.B.; Frankenschmidt, A.; Hiort, O.; Wudy, S.A.; van der Werf-Grohmann, N.; Superti-Furga, A.; Schwab, K.O.
Difficulties in diagnosis and treatment of 5 alpha-reductase type 2 deficiency in a newborn with 46,XY DSD
Horm. Res. Paediatr.
74
67-71
2010
Homo sapiens (P31213)
Manually annotated by BRENDA team
Wang, X.; Liao, J.; Yin, D.; Zhan, F.; Dai, S.; Xie, G.; Sang, X.
Establishment of a novel model for studying the effects of extracts of Chinese herb medicine on human type II 5alpha-reductase in vitro.
Yakugaku Zasshi
130
1207-1214
2010
Homo sapiens (P31213), Homo sapiens
Manually annotated by BRENDA team
Gillespie, C.; Almli, L.; Smith, A.; Bradley, B.; Kerley, K.; Crain, D.; Mercer, K.; Weiss, T.; Phifer, J.; Tang, Y.; Cubells, J.; Binder, E.; Conneely, K.; Ressler, K.
Sex dependent influence of a functional polymorphism in steroid 5-alpha-reductase type 2 (SRD5A2) on post-traumatic stress symptoms
Am. J. Med. Genet. B Neuropsychiatr. Genet.
162
283-292
2013
Homo sapiens (P31213)
Manually annotated by BRENDA team
Aggarwal, S.; Thareja, S.; Bhardwaj, T.R.; Haupenthal, J.; Hartmann, R.W.; Kumar, M.
Synthesis and biological evaluation of novel unsaturated carboxysteroids as human 5alpha-reductase inhibitors: a legitimate approach
Eur. J. Med. Chem.
54
728-739
2012
Homo sapiens (P18405), Homo sapiens (P31213)
Manually annotated by BRENDA team
Li, J.; Ding, Z.; Wang, Z.; Lu, J.F.; Maity, S.N.; Navone, N.M.; Logothetis, C.J.; Mills, G.B.; Kim, J.
Androgen regulation of 5alpha-reductase isoenzymes in prostate cancer: implications for prostate cancer prevention
PLoS ONE
6
e28840
2011
Homo sapiens, Homo sapiens (P31213), Homo sapiens (Q9H8P0)
Manually annotated by BRENDA team
Arellano, Y.; Bratoeff, E.; Garrido, M.; Soriano, J.; Heuze, Y.; Cabeza, M.
New ester derivatives of dehydroepiandrosterone as 5alpha-reductase inhibitors
Steroids
76
1241-1246
2011
Homo sapiens
Manually annotated by BRENDA team
Srivilai, J.; Rabgay, K.; Khorana, N.; Waranuch, N.; Nuengchamnong, N.; Wisuitiprot, W.; Chuprajob, T.; Changtam, C.; Suksamrarn, A.; Chavasiri, W.; Sornkaew, N.; Ingkaninan, K.
Anti-androgenic curcumin analogues as steroid 5-alpha reductase inhibitors
Med. Chem. Res.
26
1550-1556
2017
Homo sapiens, Homo sapiens CRL-1740
-
Manually annotated by BRENDA team
Srivilai, J.; Rabgay, K.; Khorana, N.; Waranuch, N.; Nuengchamnong, N.; Wisuitiprot, W.; Chuprajob, T.; Changtam, C.; Suksamrarn, A.; Chavasiri, W.; Sornkaew, N.; Ingkaninan, K.
Anti-androgenic curcumin analogues as steroid 5-alpha reductase inhibitors
Med. Chem. Res.
26
1550-1556
2017
Homo sapiens, Homo sapiens CRL-1740
-
Manually annotated by BRENDA team
Karnsomwan, W.; Netcharoensirisuk, P.; Rungrotmongkol, T.; De-Eknamkul, W.; Chamni, S.
Synthesis, biological evaluation and molecular docking of avicequinone C analogues as potential steroid 5alpha-reductase inhibitors
Chem. Pharm. Bull.
65
253-260
2017
Homo sapiens
Manually annotated by BRENDA team
Peng, H.M.; Valentin-Goyco, J.; Im, S.C.; Han, B.; Liu, J.; Qiao, J.; Auchus, R.J.
Expression in Escherichia Coli, purification, and functional reconstitution of human steroid 5alpha-reductases
Endocrinology
161
bqaa117
2020
Homo sapiens (P18405), Homo sapiens (P31213)
Manually annotated by BRENDA team
Gent, R.; du Toit, T.; Swart, A.C.
11alpha-Hydroxyprogesterone, a potent 11alpha-hydroxysteroid dehydrogenase inhibitor, is metabolised by steroid-5alpha-reductase and cytochrome P450 17alpha-hydroxylase/17,20-lyase to produce C11alpha-derivatives of 21-deoxycortisol and 11-hydroxyandrostenedione in vitro
J. Steroid Biochem. Mol. Biol.
191
105369
2019
Homo sapiens (P18405), Homo sapiens (P31213)
Manually annotated by BRENDA team
Xiao, Q.; Wang, L.; Supekar, S.; Shen, T.; Liu, H.; Ye, F.; Huang, J.; Fan, H.; Wei, Z.; Zhang, C.
Structure of human steroid 5alpha-reductase 2 with the anti-androgen drug finasteride
Nat. Commun.
11
5430
2020
Homo sapiens (P31213)
Manually annotated by BRENDA team