1.1.1.145 (+)-gossypol potent inhibitor 6332 1.1.1.145 (+)-gossypol potent inhibitor, competitive 6332 1.1.1.145 (-)-gossypol potent inhibitor 6331 1.1.1.145 (-)-gossypol weak inhibitor, competitive 6331 1.1.1.145 (12S,12aS,14bR)-N,N,12a,14b-tetramethyl-3-oxo-1,2,3,4,5,6,7,9,9a,9b,10,11,12,12a,13,14,14a,14b-octadecahydroazepino[3,2,1-de]cyclopenta[i]phenanthridine-12-carboxamide - 89491 1.1.1.145 (1R,4S,9aR,11aR)-4,9a,11a-trimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one - 15070 1.1.1.145 (1R,9aR,11aR)-9a,11a-dimethyl-1-((R)-6-methylheptan-2-yl)-3,3a,3b,4,5,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridin-7(2H)-one - 15071 1.1.1.145 (1S,8bS,10aS)-N,N-diethyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide - 15067 1.1.1.145 (1S,8bS,10aS)-N-tert-butyl-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,7,7a,8,8a,8b,8c,9,10,10a-hexadecahydrocyclopenta[i]cyclopropa[a]phenanthridine-1-carboxamide - 89494 1.1.1.145 (1S,9aR,11aS)-1-(4,5-diphenyl-4,5-dihydro-1,3-oxazol-2-yl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[i]phenanthridin-7-one - 89483 1.1.1.145 (1S,9aR,11aS)-5-butyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89490 1.1.1.145 (1S,9aR,11aS)-5-hexyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89488 1.1.1.145 (1S,9aR,11aS)-6-ethyl-N,N,9a,11a-tetramethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89487 1.1.1.145 (1S,9aR,11aS)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid - 89479 1.1.1.145 (1S,9aR,11aS)-9a,11a-dimethyl-N-[4-(morpholin-4-yl)phenyl]-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89480 1.1.1.145 (1S,9aR,11aS)-N,N,5,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89486 1.1.1.145 (1S,9aR,11aS)-N,N,6,9a,11a-pentamethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89485 1.1.1.145 (1S,9aR,11aS)-N,N,9a,11a-tetramethyl-7-oxo-5-propyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89489 1.1.1.145 (1S,9aR,11aS)-N-(2,5-di-tert-butylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89482 1.1.1.145 (1S,9aR,11aS)-N-(2-benzoylphenyl)-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89481 1.1.1.145 (1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 89484 1.1.1.145 (1S,9aR,11aS)-N-[2-tert-butyl-5-(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxamide - 15069 1.1.1.145 (4aR,6aS,7S)-7-[2,5-bis(trifluoromethyl)benzoyl]-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-2H-indeno[5,4-f]quinolin-2-one - 89493 1.1.1.145 (4aR,6aS,7S)-N-tert-butyl-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide - 89492 1.1.1.145 +/-gossypol potent, competitive 259761 1.1.1.145 16-cyano-17-keto-trilostane i.e 2,16-dicyano-4,5-epoxy-androstane-3,17-dione. Competitive, selective inhibitor of wild-type enzyme and chimeric S194G-1 mutant of the enzyme (3beta-HSD1). Noncompetitive inhibitor of chimeric R195P-1 mutant of the enzyme. Selective inhibition of 3beta-HSD1 may prevent spontaneous premature birth; i.e 2,16-dicyano-4,5-epoxy-androstane-3,17-dione. noncompetitive inhibitor; selective inhibitor 259755 1.1.1.145 17alpha-hydroxypregnenolone competitive inhibition 2809 1.1.1.145 17beta-acetoxy-trilostane - 74598 1.1.1.145 17beta-estradiol - 745 1.1.1.145 2,16-dicyano-4,5-epoxy-androstane-3,17-dione competitively inhibits 3beta-HSD1 259760 1.1.1.145 20alpha-hydroxy-4-pregnen-3-one - 6435 1.1.1.145 20beta-hydroxy-4-pregnen-3-one - 91214 1.1.1.145 3-Chloroacetylpyridine adenine dinucleotide - 91395 1.1.1.145 4-nonylphenol downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested 7529 1.1.1.145 4alpha,5alpha-epoxy-testosterone - 7759 1.1.1.145 5'-fluorosulfonylbenzoyl adenosine - 91807 1.1.1.145 5,10-Secoestr-4-yne-3,10,17-trione irreversible 91828 1.1.1.145 6-hydroxyflavone 0.00056 mM, 50% inhibition; competitive 8461 1.1.1.145 6-hydroxyflavone very potent, competitive 8461 1.1.1.145 abiraterone - 5036 1.1.1.145 AgNO3 - 360 1.1.1.145 androstenedione - 1319 1.1.1.145 apigenin - 515 1.1.1.145 apigenin 0.13 mM, 50% inhibition 515 1.1.1.145 Biochanin A - 1435 1.1.1.145 Biochanin A 0.00094 mM, 50% inhibition 1435 1.1.1.145 Biochanin A very potent 1435 1.1.1.145 bis (2-butoxyethyl) phthalate moderate inhibitor, competitive 259758 1.1.1.145 bisphenol A potent, competitive 3723 1.1.1.145 Cd2+ 1 mM: strong 52 1.1.1.145 Cd2+ - 52 1.1.1.145 Cetylpyridinium chloride - 9125 1.1.1.145 Co2+ 1 mM: weak, 100 mM: strong 23 1.1.1.145 Co2+ - 23 1.1.1.145 corticosterone 0.08 mM, 50% inhibition 1103 1.1.1.145 Cu2+ 1 mM: strong 19 1.1.1.145 Cu2+ - 19 1.1.1.145 cyanoketone 0.0000076 mM, 50% inhibition; competitive 23053 1.1.1.145 daidzein - 848 1.1.1.145 daidzein 0.0033 mM, 50% inhibition 848 1.1.1.145 daidzein very potent 848 1.1.1.145 dehydroepiandrosterone 0.01 mM reduced conversion of pregnenolone to 50% 275 1.1.1.145 deoxycorticosterone - 1753 1.1.1.145 di-heptyl phthalate potent inhibitor, competitive 259757 1.1.1.145 di-n-butyl phthalate potent inhibitor, competitive 26534 1.1.1.145 di-n-octyl phthalate weak inhibitor 74599 1.1.1.145 dicyclohexyl phthalate moderate inhibitor, competitive 4705 1.1.1.145 diethyldicarbonate - 310 1.1.1.145 diethylhexyl phthalate downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested 143590 1.1.1.145 diethylstilbestrol downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested 1679 1.1.1.145 Disulfiram - 986 1.1.1.145 drospirenone - 217229 1.1.1.145 epostane - 2244 1.1.1.145 epostane inhibits the 3beta-HSD activity of the wild-type 1 isozyme with 14–17fold greater affinity compared to the wild-type 2 isozyme and mutant H156Y; inhibits the 3beta-HSD activity of the wild-type 1 isozyme with 14–17fold greater affinity compared to the wild-type 2 isozyme and mutant H156Y 2244 1.1.1.145 epostane competitive inhibition 2244 1.1.1.145 epostane inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD2. Epostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2; inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD. Epostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2 2244 1.1.1.145 estradiol 0.0005 mM, 40% inhibition, 0.001 mM, 62% inhibition 897 1.1.1.145 estradiol-17beta - 1504 1.1.1.145 ethynylestradiol - 12525 1.1.1.145 etomidate very potent, competitive 14447 1.1.1.145 Fe2+ 1 mM: weak, 100 mM: strong 25 1.1.1.145 flavanones diverse derivatives, inhibitory potential determination, overview 132133 1.1.1.145 flavones diverse derivatives, inhibitory potential determination, overview 32220 1.1.1.145 formononetin - 2655 1.1.1.145 formononetin 0.0032 mM, 50% inhibition 2655 1.1.1.145 formononetin potent 2655 1.1.1.145 genistein - 377 1.1.1.145 genistein 0.00026 mM, 50% inhibition; competitive 377 1.1.1.145 genistein very potent, competitive 377 1.1.1.145 Hexestrol - 2407 1.1.1.145 Hg2+ - 33 1.1.1.145 HPTE potent inhibitor, competitive 259759 1.1.1.145 isoflavones diverse derivatives, inhibitory potential determination, overview 20751 1.1.1.145 ketoconazole downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested 483 1.1.1.145 ketoconazole very potent 483 1.1.1.145 lauric acid 0.05 mM, less than 10% inhibition 959 1.1.1.145 medroxyprogesterone potent 49193 1.1.1.145 methoxychlor moderate, noncompetitive 32286 1.1.1.145 methoxychlor insecticide, potent inhibitor, competitive 32286 1.1.1.145 Mn2+ 1 mM: weak 11 1.1.1.145 monooctyltin 0.081 mM, 50% inhibition; inhibition mechanism, overview 55874 1.1.1.145 additional information structure-inhibition relationship 2 1.1.1.145 additional information no inhibition by quercetin, apigenin, genistein, daidzein, enterodiol, and enterolactone 2 1.1.1.145 myricetin 0.011 mM, 50% inhibition 484 1.1.1.145 myricetin moderate 484 1.1.1.145 myristic acid 0.05 mM, less than 10% inhibition 876 1.1.1.145 N-(Anilino-naphthyl-4)-maleimide - 94160 1.1.1.145 N-Iodoacetyl-N'-(5-sulfo-1-naphthyl)ethylene diamine - 96888 1.1.1.145 NADH mixed type inhibition 8 1.1.1.145 nestorone - 217228 1.1.1.145 Ni2+ 1 mM: weak, 100 mM: strong 38 1.1.1.145 Ni2+ - 38 1.1.1.145 nomegestrol acetate - 23295 1.1.1.145 Norethisterone - 44597 1.1.1.145 Norethisterone acetate - 44598 1.1.1.145 octylphenol downregulation of 3beta-hydroxysteroid dehydrogenase mRNA at all doses tested 143591 1.1.1.145 oestradiol 0.00024 mM, 50% inhibition 55875 1.1.1.145 organotin can inhibit placental HSD3B1 activity, thus blocking the formation of progesterone and disrupting pregnancy 259756 1.1.1.145 p-chloromercuribenzoate - 43 1.1.1.145 phenylhexane - 68827 1.1.1.145 pregnenolone competitive inhibition 525 1.1.1.145 progesterone - 286 1.1.1.145 progesterone 0.026 mM, 50% inhibition 286 1.1.1.145 progesterone 0.025 mM, 44% inhibition, 0.05 mM, 67% inhibition 286 1.1.1.145 prunetin - 16807 1.1.1.145 puerarin - 21884 1.1.1.145 quercetin 0.084 mM, 50% inhibition 137 1.1.1.145 quercetin - 137 1.1.1.145 quercetin potent 137 1.1.1.145 resveratrol potent, competitive 799 1.1.1.145 Stilbestrol - 10783 1.1.1.145 testosterone - 284 1.1.1.145 testosterone 0.0086 mM, 50% inhibition 284 1.1.1.145 tributyltin 0.012 mM, almost complete loss of activity; complete inhibition at 0.012 mM, the inhibition mechanism is not entirely competitive, overview 5717 1.1.1.145 tributyltin potent, competitive 5717 1.1.1.145 tributyltin moderate inhibitor, competitive 5717 1.1.1.145 trilostane i.e. 4alpha,5-epoxy-3,17beta-dihydroxy-5alpha-androst-2-en-2-carbonitrile 1479 1.1.1.145 trilostane 0.004 mM, 50% inhibition 1479 1.1.1.145 trilostane 0.005 mM, 56% inhibition, 0.025 mM, 90% inhibition; potent inhibition 1479 1.1.1.145 trilostane - 1479 1.1.1.145 trilostane specific enzyme inhibitor 1479 1.1.1.145 trilostane competitive 1479 1.1.1.145 trilostane treatment does not affect transcription or translation in liver or adrenal 1479 1.1.1.145 trilostane i.e. 2alpha-cyano-4alpha,5alpha-epoxy-17beta-ol-androstane-3-one 1479 1.1.1.145 trilostane i.e. 2alpha-cyano-4alpha,5alpha-epoxy-17beta-ol-androstane-3-one, competitive inhibition 1479 1.1.1.145 trilostane human adrenal H295R cells treated with the HSD3B2 inhibitor, trilostane, demonstrate a markedly decreased androstenedione production 1479 1.1.1.145 trilostane inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD2. Trilostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2; inhibits the dehydroepiandrosterone-induced proliferation of MCF-7 cells expressing isoform 3beta-HSD1 with 12- to 16fold lower IC50 values compared to the MCF-7 cells expressing isoform 3beta-HSD2. Trilostane also competitively inhibits purified human 3beta-HSD1 with 12fold to 16fold lower Ki values compared to the noncompetitive Ki values measured for human 3beta-HSD2. Trilostane is docked in the active site of isoform 3beta-HSD1, and residue Arg195 in 3beta-HSD1 is a potentially critical residue 1479 1.1.1.145 trilostane specific inhibitor 1479 1.1.1.145 trilostane noncompetitive inhibitor; noncompetitive inhibitor of chimeric S194G-1 mutant and chimeric R195P-1 mutant of the enzyme (3beta-HSD1). Competitive inhibition of wild-type enzyme 1479 1.1.1.145 Triphenyltin potent, competitive 12716 1.1.1.145 Zn2+ 1 mM: strong 14