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11alpha-hydroxyprogesterone + NADPH + H+
11alpha-hydroxydihydroprogesterone + NADP+
-
-
-
?
11beta,17alpha-dihydroxyprogesterone + NADPH + H+
11beta,17alpha-hydroxydihydroprogesterone + NADP+
-
-
-
?
11beta-hydroxyprogesterone + NADPH + H+
11beta-hydroxydihydroprogesterone + NADP+
-
-
-
?
17-epitestosterone + NADPH
?
-
-
-
-
?
17alpha,21-dihydroxypregn-4-ene-3,11,20-trione + NADPH
17alpha,21-dihydroxy-5alpha-pregnan-3,11,20-trione + NADP+
-
trivial name cortisone
-
ir
17alpha,21-dihydroxypregn-4-ene-3,20-dione + NADPH
17alpha,21-dihydroxy-5alpha-pregnane-3,20-dione
-
-
-
?
17alpha-hydroxyprogesterone + NADPH
17alpha-hydroxy-5alpha-pregnan-3,20-dione + NADP+
-
-
-
-
ir
17alpha-hydroxyprogesterone + NADPH + H+
17alpha-hydroxy-5alpha-pregnan-3,20-dione + NADP+
-
-
-
?
17beta-methyl-androsta-4,9-dien-3-one + NADPH
17beta-methyl-5alpha-androst-9-en-3-one + NADP+
-
-
-
?
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
20alpha-hydroxy-4-pregnen-3-one + NADPH
20alpha-hydroxy-5-beta-pregnan-3-one + NADP+
-
more reactive than progesterone
-
-
?
21-hydroxypregn-4-ene-3,20-dione + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione + NADP+
-
-
-
?
3-keto-delta4-abiraterone + NADPH + H+
? + NADP+
-
-
-
?
5alpha-pregnan-3,20-dione + NADP+
progesterone + NADPH + H+
-
-
-
-
r
androstenediol + NADPH
5alpha-androstan-3beta,17beta-diol + NADP+
-
-
-
-
ir
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
campestenone + NADPH
5alpha-campestan-3-one + NADP+
reduction at very low levels
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
cortexolone + NADPH
17alpha,21-dihydroxy-5alpha-pregnan-3,20-dione + NADP+
-
-
-
-
ir
corticosterone + NADPH + H+
5alpha-dihydrocorticosterone + NADP+
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
epitestosterone + NADPH
?
-
-
-
-
ir
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
testosterone + NADPH + H+
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
testosterone + NADPH + H+
dihydrotestosterone + NADP+
-
-
-
?
additional information
?
-
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
-
-
-
-
?
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
-
-
-
-
?
20-alpha-hydroxypregn-4-ene-3one + NADPH
20-alpha-hydroxy-5alpha-pregnan-3-one + NADP+
-
-
-
-
ir
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
-
-
-
-
?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
-
-
-
?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
-
-
-
-
?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
-
-
-
-
?
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
-
-
-
-
ir
androstenedione + NADPH + H+
5alpha-androstan-3,17-dione + NADP+
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
390592, 396192, 396196, 396199, 396200, 396201, 396203, 396204, 396205, 396209, 396210 -
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
mammalian enzymes: no reverse reaction, first step in reverse direction (enolization) occurs, but energy barrier for hydride abstraction is extremely high
-
-
ir
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
-
?
cholest-4-en-3-one + NADPH
5-alpha-cholestan-3-one + NADP+
-
-
-
-
?
corticosterone + NADPH + H+
5alpha-dihydrocorticosterone + NADP+
-
-
-
-
r
corticosterone + NADPH + H+
5alpha-dihydrocorticosterone + NADP+
-
-
-
-
r
corticosterone + NADPH + H+
5alpha-dihydrocorticosterone + NADP+
-
-
-
-
?
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
-
-
-
-
?
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
-
-
-
-
?
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
-
-
-
-
?
deoxycorticosterone + NADPH
21-hydroxy-5alpha-pregnan-3,20-dione
-
-
-
-
ir
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
-
ir
progesterone + NADPH + H+
5alpha-pregnan-3,20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
ir
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
biosynthesis of cardenolides
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
activity is higher in hypothalamus of non-lactating female rats than in lactating
-
r
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
riboflavin-deficient diet decreases the enzyme activity, after 5 weeks no activity is remaining
-
-
?
progesterone + NADPH + H+
5alpha-pregnan-3-20-dione + NADP+
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
ir
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
ir
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
17beta-hydroxy-5alpha-androstan-3-one + NADP+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
655182, 657354, 684816, 686332, 687319, 688684, 688720, 689849, 697392, 740941, 743212 -
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
r
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
5alpha-dihydrotestosterone is a potent androgen, abnormal overproduction is associated with pathologies of mainly prostate and skin, e.g. benign prostatic hyperplasia, prostate cancer, acne, androgenetic alopecia in men, and hirsutism in women, with different involvement of the isozymes
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
dihydrotestosterone is a more potent androgen, regulatory function, overview
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
reaction mechanism
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
the enzyme performs conversion of testosterone to dihydrotestosterone
-
-
r
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
5alpha-dihydrotestosterone is a more potent androgen, regulatory function, overview
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
very low activity
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
-
-
-
-
ir
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
-
-
-
-
?
testosterone + NADPH + H+
5alpha-dihydrotestosterone + NADP+ + H+
-
-
-
-
?
testosterone + NADPH + H+
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
-
-
-
r
testosterone + NADPH + H+
androstan-3alpha,17beta-diol + androstan-3beta,17beta-diol + 5alpha-dihydrotestosterone
-
reversible in the presence of coenzyme Q10 as electron-acceptor, electrons are transferred from NADPH to coenzyme Q10 via the enzyme NADPH:coenzyme Q10-oxidoreductase and then to testosterone
-
r
additional information
?
-
-
no activity for campestenone
-
-
?
additional information
?
-
-
testosterone and 20alpha-hydroxy-4-pregnen-3-one can act in place of progesterone
-
-
?
additional information
?
-
-
testosterone is less effective
-
-
?
additional information
?
-
-
testosterone is less effective
-
-
?
additional information
?
-
-
role of enzyme in initiation of spermatogenensis
-
-
?
additional information
?
-
-
neither Km nor Vmax for both corticosterone and testosterone are significantly different among reproductive periods
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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(+/-)-LY191704
-
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
(-)-epigallocatechin-3-gallate
-
i.e. EGCG, from Thea sativa, slightly inhibits the liver microsomal enzyme
(10bR)-8-chloro-4,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform II, 49% inhibition at 0.02 mM
(10bR)-8-chloro-4,5,10b-trimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
isoform II, 57% inhibition at 0.029 mM
(10bR)-8-chloro-5,10b-dimethyl-4a,5,6,10b-tetrahydrophenanthridin-2(1H)-one
-
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
-
-
(1E,4E,6E)-1,7-bis(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(2-chlorophenyl)-7-phenylhepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(3-hydroxy-4-methoxyphenyl)-7-(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(3-nitrophenyl)-7-phenylhepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(3-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-1-(4-methoxyphenyl)-7-phenylhepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-7-(3-hydroxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,4E,6E)-7-[3-(cycloprop-2-en-1-yloxy)phenyl]-1-(2-hydroxyphenyl)hepta-1,4,6-trien-3-one
-
-
(1E,6E)-1,7-bis(3,4-dihydroxyphenyl)hepta-1,6-diene-3,5-dione
-
-
(2E)-3-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-N-[2-(4-hydroxy-3-methoxyphenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
-
-
(2E)-3-(4-hydroxy-3-methoxycyclohexa-1,5-dien-1-yl)-N-[2-(4-methoxyphenyl)ethyl]prop-2-enamide
-
-
(2E,4E,6E,8E)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate
-
compound shows moderate anti-tumour activity in vivo
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl palmitoate
-
activity of 3-O-acylated (e)-epigallocatechins increases with the increasing carbon numbers of the fatty acid moiety, reaching maximum for palmitoate
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-6-ylmethyl)tetrahydrofuran-2-ol
-
-
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(1,3,5-benzotrioxepin-7-ylmethyl)tetrahydrofuran-2-ol
-
i.e. (-)-cubebin
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(2,3-dimethoxybenzyl)tetrahydrofuran-2-ol
-
-
(3R,4R)-3-(1,3-benzodioxol-5-ylmethyl)-4-(3,4-dimethoxybenzyl)tetrahydrofuran-2-ol
-
i.e. (-)-3,4-dimethoxy-3,4-desmethylenedioxycubebin
(4aS)-7-chloro-4a-methyl-2,3,4,4a-tetrahydrophenanthrene-2-carboxylic acid
-
-
(4aS,10bS)-4,10b-dimethyl-8-[(E)-2-naphthylylvinyl]-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
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
-
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
-
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
-
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
-
isoform I, 50% inhibition at 35 nM
(4aS,10bS)-8-chloro-1,4,4a,5,6,10b-hexahydrobenzo[f]quinolin-3(2H)-one
-
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
-
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
-
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
-
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
-
isoform I, 50% inhibition at 120 nM
(4E,6E)-1-(4-hydroxyphenyl)-7-phenylhepta-4,6-dien-3-one
-
-
(4R)-4,8-dimethyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
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
-
isoform I, 50% inhibition at 141 nM
(4S)-4,8-dimethyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 137 nM
(5'S)-17beta-(2-chlorophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one
-
-
(5'S)-17beta-(4-bromophenyl-4,5-dihydrooxazol-5-yl)androst-5-en-3-one
-
-
(5alpha,20-R)-4-Diazo-21-hydroxy-20-methylpregnan-3-one
-
RMI18,341
(6E)-1-(4-hydroxyphenyl)-7-phenylhept-6-en-3-one
-
-
(6R)-8-chloro-6-methyl-4,4a,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 188 nM
(Z)-((2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl) hexadec-9-enoate
-
-
1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 298 nM
1-methyl-5-(4-(2-phenylacetyl)phenyl)pyridin-2(1H)-one
-
61% inhibition of type 1 steroid 5alpha reductase at 0.01 mM
11-ketoprogesterone
-
complete inhibition
17-diisopropylcarbamoyl-2-androsten-3-carboxylate
-
-
17-diisopropylcarbamoyl-3,5-androstadien-3-carboxylate
-
-
17-diisopropylcarbamoyl-3-androsten-3-carboxyate
-
-
17-diisopropylcarbamoyl-androstan-3-carboxylate
-
-
17-tert-butylcarbamoyl-3,5-androstadien-3-carbaldehyde
-
-
17-tert-butylcarbamoyl-3,5-androstadien-3-carboxylate
-
dead-end inhibition versus testosterone
17-tert-butylcarbamoyl-3,5-androstadien-3-ol
-
-
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-hydroxyprogesterone
-
-
17alpha-methyltestosterone
-
-
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3 20-dione
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3,20-dione
17alpha-phenylcarbamoyloxy-4-pregnen-3,20-dione
17beta-(N-tert-butylcarbamoyl)androsta-3,5-diene-3-carboxylic acid
-
-
17beta-Carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids
17beta-hydroxyandrosta-1,4-dien-3-one
-
50% inhibition
17beta[3-(N-4-bromophenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-chlorophenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-ethoxyphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-ethylphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-methoxyphenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-phenyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
-
17beta[3-(N-4-tolyl)tetrahydrooxazin-2-on-6-yl]androst-4-en-3-one
-
slight inhibition
19-norandrost-4-ene-3,17-dione
-
complete inhibition
19-nortestosterone
-
complete inhibition
2,4a,9,10-tetrahydrophenanthrene-2-carboxylic acid
-
-
2,5-dihydroxy-1,4-benzoquinone
-
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
-
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
-
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
-
2-acetyl-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
-
inhibitor isolated from Thai mangrove Avicennia marina
-
2-acetylnaphtho[2,3-b]furan-4,9-dione
-
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
-
20alpha-hydroxypregn-4-en-3-one
-
competitive
21,21-pentamethylene-4-aza-5alpha-pregn-1-ene-3,20-dione
-
i.e. L685,273, suppresses testicular enzyme activity during puberty by 75-86%
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
4,16-androstadien-3-one
-
-
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
4-(biphenyl-4'-yloxy)phenylacetic acid
4-(biphenyl-4'-yloxy)phenylformic acid
4-(N-(diphenyl)acetyl-4-piperidinyloxy)benzoic acid
4-(N-(diphenyl)carbamoyl-4-piperidinyloxy)benzoic acid
4-(N-(tert-butyloxycarbonyl)-4-piperidinyloxy)benzoic acid
4-(N-adamantanoyl-4-piperidinyloxy)benzoic acid
4-Androsten-3-one-17beta-carboxylic acid
-
competitive
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
4-bromo-17alpha-(p-fluorobenzoyloxy)-4-pregnene-3,20-dione
-
competitive
4-carboxy-4'-(N,N-dicyclohexyl)-aminobiphenyl
4-carboxy-4'-(N,N-diisobutyl)-aminobiphenyl
4-carboxy-4'-(N,N-diisopropyl)-aminobiphenyl
4-carboxy-4'-(N,N-diphenyl)-aminobiphenyl
4-carboxy-4'-(N-adamantyl)-aminobiphenyl
4-Ene-3-keto-steroids
-
17beta-estradiol in high concentrations functions as an uncompetitive inhibitor
4-methyl-1,2,5,6-tetrahydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 185 nM
4-methyl-5,6-dihydro-3H-pyrido[1,2-a]quinolin-3-one
-
isoform I, 50% inhibition at 1400 nM
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
5alpha-androstane-3,17-dione
-
30% inhibition
5beta-cholestan-3-one
-
-
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-methylene-17alpha-(2-cyclohexylacetoxy)-pregn-4-ene-3,20-dione
-
-
6-methylene-17alpha-(3-cyclohexylpropionyloxy)-pregn-4-ene-3,20-dione
-
-
6-methylene-17alpha-(3-cyclopentylpropionyloxy)-pregn-4-ene-3,20-dione
-
-
6-methylene-17alpha-(4-cyclohexylbutyryloxy)-pregn-4-ene-3,20-dione
-
-
6alpha-methyl-11-ketoprogesterone
-
25% inhibition
6beta-methyl-11-ketoprogesterone
-
50% inhibition
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
AFA76
active at 0.01 mM, most potent inhibitor among non-steroid compounds tested
alpha-4-azasteroids
-
substitution of finasteride N-group by 6-azasteroids increased the rate of inhibition of type-1 5-alpha-reductases
androst-1-ene-3,17dione
-
55% inhibition
androst-4-en-3,17-dione
-
-
androst-4-ene-3,17-dione
-
complete inhibition
AS601811
active at 0.01 mM
asclepic acid
-
50% inhibition at 0.50 mM
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
Cd2+
-
1 mM: less than 20% inhibition
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
Detergents
-
e.g.: Lubrol WX, Nonidet P-40, octyl D-glucopyranoside, L-alpha-lysophosphatidylcholine, CHAPS, concentration-dependent inhibition
dihydrotestosterone
-
significantly decreases 5alpha-R1 mRNA and 5alpha-R2 mRNA expression in female rats
docosanol
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
EDTA
-
slightly inhibitory
estradiol
-
in female genital skin fibroblasts
FK143
-
i.e. 4-[3-(3-[[bis-(4-isobutyl-phenyl)-methyl]amino]-benzoyl)-indol-1-yl]-butyric acid, a non-steroidal bi-substrate inhibitor
flavins
-
and flavin analogs, high concentration
-
ginsenoside Rg3
-
a unique ginsenoside in red ginseng
kaikasaponin III
-
0.1 mM, 66.8% inhibition
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
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
Mn2+
-
1 mM: less than 20% inhibition
myristic acid
-
isoform 2, 50% inhibition at 0.004 mM
N(dicyclohexyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 55% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 43% inhibition at 0.01 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
N,N-diisobutyl-4-(4'-carboxyphenoxy)benzamide
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
N,N-diphenyl-4-(4'-carboxyphenoxy)benzamide
N-(1-adamantanoyl)piperdine-4-(2-methoxybenzyliden-4-carboxylic acid)
N-(1-adamantanoyl)piperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
N-(3,3-diphenyl)propanoylpiperidine-4-(benzylidene-4-carboxylic acid)
N-(dicyclohexyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
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)
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-acetic acid)
N-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-carboxylic acid)
N-(diphenyl)acetylpiperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
N-(diphenyl)acetylpiperidine-4-(2-methoxybenzylidene-4-carboxylic acid)
N-(diphenyl)acetylpiperidine-4-(benzylidene-3-carboxylic acid)
N-(diphenyl)acetylpiperidine-4-(benzylidene-4-acetic acid)
N-adamantyl-4-(4'-carboxyphenoxy)benzamide
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
N-phenyl-4-(4'-carboxyphenoxy)benzamide
N-tert-butyl-4-(4'-carboxyphenoxy)benzamide
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 ethyl ester
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
ONO-3805
-
a non-steroidal bi-substrate inhibitor
penta-O-galloyl-beta-D-glucose
Piper betle ethanolic whole plant extract
-
42.3% inhibition at 2 mg/ml
-
Piper cueba ethanolic fruit extract
-
28.0% inhibition at 2 mg/ml
-
Piper kadsura ethanolic leaf extract
-
19.0% inhibition at 2 mg/ml
-
Piper kadsura ethanolic rhizome extract
-
36.5% inhibition at 2 mg/ml
-
Piper kadsura ethanolic root extract
-
39.2% inhibition at 2 mg/ml
-
Piper kadsura ethanolic stem extract
-
16.9% inhibition at 2 mg/ml
-
Piper longum ethanolic whole plant extract
-
12.3% inhibition at 2 mg/ml
-
Piper methysticum ethanolic leaf extract
-
28.4% inhibition at 2 mg/ml
-
Piper methysticum ethanolic rhizome extract
-
42.5% inhibition at 2 mg/ml
-
Piper methysticum ethanolic stem extract
-
21.9% inhibition at 2 mg/ml
-
Piper nigrum ethanolic fruit extract
-
63% inhibition at 2 mg/ml
-
Piper nigrum ethanolic leaf extract
-
53.0% inhibition at 2 mg/ml
-
Piper nigrum ethanolic stem extract
-
40.8% inhibition at 2 mg/ml
-
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
soyasaponin I
-
0.1 mM, 66.8% inhibition
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
tert-butyl-4-hydroxyanisole
a mixture of two isomers of tert-butyl-4-hydroxyanisole. Competitive inhibitor
theaflavin-3'-gallate
-
i.e. TF2b, from Thea sativa, inhibits the liver microsomal enzyme
theaflavin-3,3'-digallate
theaflavin-3-gallate
-
i.e. TF2a, from Thea sativa, inhibits the liver microsomal enzyme
tocopherol
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
Unsaturated 3-carboxysteroids
-
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3 20-dione
-
-
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3 20-dione
-
-
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3,20-dione
-
-
17alpha-p-bromophenylcarbamoyloxy-4-pregnen-3,20-dione
-
-
17alpha-phenylcarbamoyloxy-4-pregnen-3,20-dione
-
-
17alpha-phenylcarbamoyloxy-4-pregnen-3,20-dione
-
-
17beta-Carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids
-
formation of enzyme-NADP+-inhibitor complex
17beta-Carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids
-
formation of enzyme-NADP+-inhibitor complex
17beta-estradiol
-
-
17beta-estradiol
-
noncompetitive inhibition
3-Androstene-3-carboxylic acids
-
-
3-Androstene-3-carboxylic acids
-
uncompetitive
4-(4'-formylphenoxy)benzoic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.007 mM
4-(4'-formylphenoxy)benzoic acid
-
37°C, pH 6.6, 7% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 16% inhibition at 0.01 mM, isoform II
4-(biphenyl-4'-yloxy)phenylacetic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.00006 mM
4-(biphenyl-4'-yloxy)phenylacetic acid
-
37°C, pH 6.6, 29% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.0096 mM, isoform II
4-(biphenyl-4'-yloxy)phenylformic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.000006 mM
4-(biphenyl-4'-yloxy)phenylformic acid
-
37°C, pH 6.6, 21% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 15% inhibition at 0.01 mM, isoform II
4-(N-(diphenyl)acetyl-4-piperidinyloxy)benzoic acid
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0013 mM
4-(N-(diphenyl)acetyl-4-piperidinyloxy)benzoic acid
-
isoform 1, pH 6.6, 37°C, 62% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 58% inhibition at 0.01 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-(diphenyl)carbamoyl-4-piperidinyloxy)benzoic acid
-
isoform 1, pH 6.6, 37°C, 53% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 50% 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-(tert-butyloxycarbonyl)-4-piperidinyloxy)benzoic acid
-
isoform 1, pH 6.6, 37°C, 4% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 12% inhibition at 0.01 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-(N-adamantanoyl-4-piperidinyloxy)benzoic acid
-
isoform 1, pH 6.6, 37°C, 18% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 21% inhibition at 0.01 mM
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
-
competitive against progesterone, reversible, transition state analog
4-Aza-4-methyl-5alpha-pregnane-3,20-dione
-
-
4-azasteroids
-
competitive inhibition
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-dicyclohexyl)-aminobiphenyl
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0014 mM, DU145 cells, 44% inhibition at 0.003 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-diisobutyl)-aminobiphenyl
-
37°C, pH 6.6, 24% inhibition at 0.001 mM, isoform I, 37°C, pH 5.5, 37% inhibition at 0.001 mM, isoform II
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-diisopropyl)-aminobiphenyl
-
37°C, pH 6.6, 4% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 10% inhibition at 0.01 mM, isoform II
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,N-diphenyl)-aminobiphenyl
-
37°C, pH 6.6, 50% inhibition at 0.00046 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.003 mM, isoform II
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-carboxy-4'-(N-adamantyl)-aminobiphenyl
-
37°C, pH 6.6, 50% inhibition at 0.0056 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.01 mM, isoform II
4-methyl-4-azasteroids
-
4-MA is a 90-fold more potent inhibitor than finasteride in the DU 145 cell-line; competitive
-
4-methyl-4-azasteroids
-
competitive
-
4-methyl-4-azasteroids
-
competitive
-
4-methyl-4-azasteroids
-
competitive
-
4-methyl-4-azasteroids
-
competitive
-
4-methyl-azasteroid
-
-
acrylate episteride
-
-
Ca2+
-
-
Ca2+
-
1 mM: less than 20% inhibition
Cu2+
-
-
dutasteride
-
inhibits both isozymes, used in treatment of benign protstate hyperplasia, reduction of serum dihydrotestosterone levels
dutasteride
-
slow, time-dependent inhibitor, more efficient than finasteride
dutasteride
-
90% inhibition of type-2 and type-1 5alpha-reductases at clinical dosage of 0.5 mg/day
dutasteride
-
inhibitor of isoenzymes 5-alpha-reductase type 1 and type 2
dutasteride
-
0.5 mg/day, dual 5alpha-reductase inhibitor
dutasteride
-
dual 5alpha-reductase inhibitor, 45fold more effective in inhibiting type 1 5alpha-reductase and 2fold more effective in inhibiting type 2 5alpha-reductase than finasteride
dutasteride
-
0.5 mg/day, inhibitor of type 1 and type 2 5alpha reductase; treatment with 0.5 mg daily for 1 year leads to reduced enzyme activity
dutasteride
-
dual 5alpha-reductase inhibitor
estradiol-17beta
-
-
estradiol-17beta
-
high concentration
ethinylestradiol
-
50% inhibition at 0.81 mM
ethinylestradiol
-
63.3% inhibition at 1 mM
finasteride
-
17-beta-N-tert-butylcarbonyl-4-aza-5alpha-androstan-1-en-3-one is a time-dependent, apparently irreversible inhibitor of 5alpha-reductases, but does not fully inhibit the activity of 5alpha-reductase in vivo
finasteride
-
replacement of residues 26-29 (AVFA) from isozyme 1 with residues 21-24 (GALA) from isozyme 2 increases the resistance to finasteride, what confirms that residues 26-29 from isozyme 1 are involved in the inhibitor/substrate binding but suggest residues 21-29 from isozyme 2 are not. More findings indicate that residues 15-17 of human 5 alpha-reductase 2 participate in inhibitor/substrate binding
finasteride
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.000003 mM, DU145 cells, 50% inhibition at 0.00041 mM
finasteride
-
4-azasteroid, specific for isozyme 5alphaR-2, used in treatment of benign protstate hyperplasia, reduction of serum dihydrotestosterone levels
finasteride
-
i.e. 17beta-(N-tert-butylcarbamoyl)-4-aza-5alpha-androst-1-en-3-one
finasteride
-
slow, time-dependent inhibitor
finasteride
-
70% inhibition of type-2 5alpha-reductase at clinical dosage of 5.0 mg/day
finasteride
-
5alphaR2 inhibitor
finasteride
-
5 mg/day, selective inhibitor of isoenzyme 5-alpha-reductase type 2
finasteride
-
5.0 mg/day, effective inhibitor of type 2 5alpha-reductase
finasteride
-
type 2 5alpha-reductase inhibitor
finasteride
-
5.0 mg/day, inhibits type 2 5alpha-reductase; treatment with 5 mg daily for 1 year leads to reduced enzyme activity
finasteride
-
competitive
finasteride
-
37°C, pH 6.6, 50% inhibition at 0.00001 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.00001 mM, isoform II
finasteride
-
type 2 5alpha-reductase inhibitor
finasteride
-
0.025 mM, 78.3% inhibition
finasteride
active at 0.01 mM
ginsenoside Ro
-
topical administration of ginsenoside Ro at 0.2 mg/mouse to shaved skin inhibits hair regrowth suppression after shaving in the testosterone-treated C57BL/6 mice
ginsenoside Ro
-
predominant ginsenoside in the rhizome of ginseng
linoleic acid
-
isoform 1, 50% inhibition at 0.013 mM, isoform 2, 50% inhibition at 0.035 mM
linoleic acid
-
50% inhibition at 0.37 mM
MK386
-
steroidal inhibitor
MK386
-
potent inhibitory effect on 5alphaR1
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-dicyclohexyl-4-(4'-carboxyphenoxy)benzamide
-
37°C, pH 6.6, 50% inhibition at 0.0041 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.01 mM, isoform II
N,N-diisobutyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 46% inhibition at 0.01 mM
N,N-diisobutyl-4-(4'-carboxyphenoxy)benzamide
-
37°C, pH 6.6, 18% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 22% inhibition at 0.01 mM, isoform II
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-diisopropyl-4-(4'-carboxyphenoxy)benzamide
-
37°C, pH 6.6, 4% inhibition at 0.01 mM, isoform I
N,N-diphenyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.00085 mM
N,N-diphenyl-4-(4'-carboxyphenoxy)benzamide
-
37°C, pH 6.6, 50% inhibition at 0.0045 mM, isoform I, 37°C, pH 5.5, 26% inhibition at 0.001 mM, isoform II
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)piperdine-4-(2-methoxybenzyliden-4-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0011 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.0011 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-(1-adamantanoyl)piperidine-4-(2-fluorobenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 52% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 51% inhibition at 0.01 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-(3,3-diphenyl)propanoylpiperidine-4-(benzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0016 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.00088 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-fluorobenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0018 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.003 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-3-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 35% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 25% inhibition at 0.01 mM
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-acetic acid)
-
isoform 1, pH 6.6, 37°C, 66% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 56% inhibition at 0.01 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-(dicyclohexyl)acetylpiperidine-4-(benzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 51% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.00008 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-fluorobenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0011 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.0011 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-(2-methoxybenzylidene-4-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0019 mM, isoform 2, pH 5.5, 37°C, 50% inhibition at 0.00094 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-3-carboxylic acid)
-
isoform 1, pH 6.6, 37°C, 49% inhibition at 0.01 mM, isoform 2, pH 5.5, 37°C, 43% 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-(diphenyl)acetylpiperidine-4-(benzylidene-4-acetic acid)
-
isoform 1, pH 6.6, 37°C, 50% inhibition at 0.0045 mM, isoform 2, pH 5.5, 37°C, 63% inhibition at 0.01 mM
N-adamantyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.00038 mM
N-adamantyl-4-(4'-carboxyphenoxy)benzamide
-
37°C, pH 6.6, 50% inhibition at 0.0082 mM, isoform I, 37°C, pH 5.5, 50% inhibition at 0.008 mM, isoform II
N-cyclohexyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0023 mM
N-cyclohexyl-4-(4'-carboxyphenoxy)benzamide
-
37°C, pH 6.6, 17% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 35% inhibition at 0.01 mM, isoform II
N-phenyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.001 mM
N-phenyl-4-(4'-carboxyphenoxy)benzamide
-
37°C, pH 6.6, 22% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 39% inhibition at 0.01 mM, isoform II
N-tert-butyl-4-(4'-carboxyphenoxy)benzamide
-
pH 5.5, 37°C, BPH tissue, 50% inhibition at 0.0028 mM
N-tert-butyl-4-(4'-carboxyphenoxy)benzamide
-
37°C, pH 6.6, 5% inhibition at 0.01 mM, isoform I, 37°C, pH 5.5, 26% inhibition at 0.01 mM, isoform II
NADP+
-
product inhibition
oleic acid
-
isoform 1, 50% inhibition at 0.004 mM, isoform 2, 50% inhibition above 0.1 mM
oleic acid
-
50% inhibition at 0.44 mM
p-chloromercuribenzoate
-
complete inhibition
p-chloromercuribenzoate
-
-
palmitic acid
-
isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
palmitic acid
-
50% inhibition at 1.35 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
penta-O-galloyl-beta-D-glucose
-
i.e. 5GG, from Thea sativa, inhibits the liver microsomal enzyme
progesterone
-
competitive
progesterone
-
complete inhibition
progesterone
-
competitive
progesterone
-
competitive
testosterone
-
poor competitive inhibitor
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
theaflavin-3,3'-digallate
-
i.e. TF3, from Thea sativa, inhibits the liver microsomal enzyme
turosteride
-
-
Unsaturated 3-carboxysteroids
-
-
-
Unsaturated 3-carboxysteroids
-
-
-
Zn2+
-
-
additional information
-
-
-
additional information
-
kinetic inhibition mechanism of steroidal and non-steroidal inhibitors, competitive steroidal inhibitors, type A or type B, act with a substrate-like or a product-like transition state, type C uncompetitive steroidal inhibitors, overview
-
additional information
-
synthesis of diverse steroidal tetrahydrooxazin-2-ones as potential inhibitors of the enzyme, IC50 of inhibitory compounds, overview
-
additional information
-
no inhibition of type 2 steroid 5alpha reductase at 0.01 mM N,N-diisopropyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide, N-allyl-2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamide, N,N-diisopropyl-2-(4-(1-methyl-6-oxopiperidin-3-yl)phenoxy)acetamide, 1-methyl-5-(4-(2-phenylacetyl)phenyl)pyridin-2(1H)-one, N,N-diisopropyl-2-(4-(2-methyl-4-oxo-3,4-dihydropyridin-1(2H)-yl)phenoxy) acetamide, 2-(16-(acetylthio)hexadecanamido)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate, and 2-(2-(16-(acetylthio)hexadecanamido)ethoxy)ethyl 6-(2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenoxy)acetamido)hex-4-enoate
-
additional information
inhibitory effects on SRD5A2 of Chinese medicine herb extracts, of Anemarrhena aspholoides rhizomes, Pellodendron amurense bark, and Cinnamomum cassia bark, collected in China, Korea, and Japan, overview
-
additional information
-
inhibitory effects on SRD5A2 of Chinese medicine herb extracts, of Anemarrhena aspholoides rhizomes, Pellodendron amurense bark, and Cinnamomum cassia bark, collected in China, Korea, and Japan, overview
-
additional information
-
synthesis and inhibitory potency of compounds, IC50 values, and affinity for the androgen receptor in prostate, overview
-
additional information
-
not inhibitory: stearic acid
-
additional information
-
theaflavin, gallic acid, and n-propyl gallate are poor inhibitors, physiological effects of inhibitors in vivo, overview
-
additional information
-
no inhibitory activity of yangonin, (+)-methysticin, (+)-kawain, 5,6-dehydrokawain, and 7,8-epoxyyangonin against 5alpha reductase; yangonin, (+)-methysticin, (+)-kawain, 5,6-dehydrokawain, and 7,8-epoxyyangonin show no significant 5alpha-reductase inhibitory activity
-
additional information
-
flowers of Pueraria thomsonii, 50% ethanolic extract shows inhibitory activity of 60.2%
-
additional information
-
enzyme is not inhibited by finasteride
-
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