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1.3.1.22: 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+)

This is an abbreviated version!
For detailed information about 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+), go to the full flat file.

Word Map on EC 1.3.1.22

Reaction

a 3-oxo-5alpha-steroid
+
NADP+
=
a 3-oxo-DELTA4-steroid
 +
NADPH
 +
H+

Synonyms

3-oxosteroid 5alpha-reductase, 3-oxosteroid DELTA4-dehydrogenase, 4-ene-3-oxosteroid 5alpha-reductase, 4-ene-5alpha-reductase, 5 alpha-R2, 5 alpha-reductase type 2, 5-alpha reductase I, 5-alpha reductase II, 5-alpha-reductase type 1, 5-alpha-reductase type 2, 5a-reductase type 1, 5a-reductase type 2, 5A2, 5alpha-R1, 5alpha-R2, 5alpha-reductase 1, 5alpha-reductase II, 5alpha-reductase type 1, 5alpha-reductase type 2, 5alpha-reductase type II, 5alpha-SR2, 5alphaR, 5alphaR type 2, 5alphaR1, 5alphaR2, AtDET2, brainneurosteroidogenic 5x02-reductase 1, cholest-4-en-3-one 5alpha-reductase, cortisone alpha-reductase, cortisone DELTA 4-5alphareductase, DCC71_03205, DELTA4-3-ketosteroid 5alpha-oxidoreductase, DELTA4-3-ketosteroid reductase (5alpha), DELTA4-3-oxosteroid-5 alpha-reductase, DELTA4-5alpha-reductase, DELTA4-steroid 5alpha-reductase (progesterone), EC 1.3.1.30, EC 1.3.1.4, LeDET2, microsomal steroid reductase (5alpha), More, NADPH:DELTA4-3-oxosteroid-5alpha-oxidoreductase, neurosteroidogenic 5alpha-reductase 1, progesterone 5alpha-reductase, reduced nicotinamide adenine dinucleotide phosphate:DELTA4-3-ketosteroid 5alpha-oxidoreductase, reductase, cholestenone 5alpha-, reductase, cortisone DELTA: 4-5alpha-, reductase, progesterone 5alpha-, S5alphaR, SRD5A1, SRD5A2, SRDA1, SRDA2, SRDA3, steroid 5-alpha reductase, steroid 5-alpha-reductase, steroid 5alpha reductase type 2, steroid 5alpha-hydrogenase, steroid 5alpha-reductase, steroid 5alpha-reductase type II, testosterone 5alpha-reductase, testosterone delta4-5alpha-reductase, testosterone delta4-hydrogenase, type 1 5alpha-reductase, type 1 5alphaR, type 1 SR, type 1 steroid 5alpha reductase, type 1 steroid 5alpha-reductase, type 2 5alpha-reductase, type 2 5alphaR, type 2 SR, type 2 steroid 5alpha reductase, type 2 steroid 5alpha-reductase, type II 5alpha-reductase, type-1 5alpha-reductase, type-2 5alpha-reductase

ECTree

     1 Oxidoreductases
         1.3 Acting on the CH-CH group of donors
             1.3.1 With NAD+ or NADP+ as acceptor
                1.3.1.22 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+)

Inhibitors

Inhibitors on EC 1.3.1.22 - 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+)

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-methysticin
-
-
(+/-)-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
10-azasteroids
-
several
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-estradiol
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-azasteroids
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-MA
active at 0.01 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
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-azasteroids
-
several
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
acrylate episteride
AFA131
active at 0.01 mM
AFA192
active at 0.01 mM
AFA27
active at 0.01 mM
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
androst-4-enedione
-
-
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
beta-sitosterol
-
-
Biochanin A
-
-
bisdemethoxycurcumin
-
22.2% inhibition at 0.3 mM
Cd2+
-
1 mM: less than 20% inhibition
cholest-5-en-3-one
-
-
cholestanone
-
-
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
dutasteride
EDTA
-
slightly inhibitory
epristeride
-
-
estradiol
-
in female genital skin fibroblasts
estradiol-17beta
ethinylestradiol
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
flavins
-
and flavin analogs, high concentration
-
genistein
-
-
ginsenoside Rg3
-
a unique ginsenoside in red ginseng
ginsenoside Ro
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
linoleic acid
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
MK434
-
-
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
NADP+
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
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
p-chloromercuribenzoate
palmitic acid
PD17
active at 0.01 mM
PD91
active at 0.01 mM
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
-
piperine
-
-
progesterone
riboflavin
-
-
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
testosterone
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
turosteride
Unsaturated 3-carboxysteroids
-
VG106
active at 0.01 mM
yangonin
-
-
additional information
-