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1.14.14.19: steroid 17alpha-monooxygenase

This is an abbreviated version!
For detailed information about steroid 17alpha-monooxygenase, go to the full flat file.

Word Map on EC 1.14.14.19

Reaction

a C21-steroid
+
[reduced NADPH-hemoprotein reductase]
 +
O2
=
a 17alpha-hydroxy-C21-steroid
 +
[oxidized NADPH-hemoprotein reductase]
 +
H2O

Synonyms

17 alpha-hydroxylase/C17,20-lyase, 17,20-lyase, 17-alpha-hydroxylase/C17-20 lyase, 17-hydroxylase/17,20-lyase, 17-hydroxylase/C17,20-lyase, 17alphahydroxylase, 17alpha-hydroxylase, 17alpha-hydroxylase 17,20 lyase, 17alpha-hydroxylase-17,20-lyase, 17alpha-hydroxylase-C17,20 lyase, 17alpha-hydroxylase-C17,20-lyase, 17alpha-hydroxylase/17,20 lyase, 17alpha-hydroxylase/17,20-lyase, 17alpha-hydroxylase/C(17,20)-lyase, 17alpha-OHase, 17OHD, CYP 17, CYP17, CYP17A1, CYPXVII, cytochrome P-450 (P45017alpha,lyase), cytochrome P-45017alpha, cytochrome P450 17, cytochrome P450 17A1, cytochrome P450 17A2, cytochrome P450 17alpha-hydroxylase, cytochrome P450 17alpha-hydroxylase-17,20-lyase, cytochrome P450 17alpha-hydroxylase/17,20 lyase, cytochrome P450 17alpha-hydroxylase/17,20-lyase, cytochrome p450 17alpha-hydroxylase/C(17,20)-lyase, cytochrome P450 17alpha-hydroxylase/C17,20-lyase, cytochrome P450 17alpha-hydroxylase/c17-20 lyase, cytochrome P45017alpha, cytochrome P450c17, cytochrome P450c17alpha, cytochromeP450 17alpha-hydroxylase/C17-20 lyase, EC 1.14.1.7, EC 1.14.99.9, EC 1.99.1.9, P450 17, P450 17A1, P450(17alpha), P450-17alpha, P450-C17, P45017alpha, P450c17, P450c17-I, Steroid 17-alpha-hydroxylase/17,20 lyase, steroid 17alpha-hydroxylase, steroidogenic cytochrome P450 17A1

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.14.19 steroid 17alpha-monooxygenase

Inhibitors

Inhibitors on EC 1.14.14.19 - steroid 17alpha-monooxygenase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
(+)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
(+)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
(+)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
(-)-7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
(-)-N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
(-)-N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
(1S)-1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropan-1-ol
-
-
(2Z)-3-[3-hydroxy-4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]phenyl]prop-2-enoic acid
-
41.34% inhibition at 0.01 mM
(2Z)-3-[4-methoxy-3-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]phenyl]prop-2-enoic acid
-
43.27% inhibition at 0.01 mM
(2Z)-3-[4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]phenyl]prop-2-enoic acid
-
45.5% inhibition at 0.01 mM
(4-(benzo[b]thiophen-5-yl)phenyl)methanol
-
2% inhibition at 200 nM and 39% inhibition at 0.002 mM
(S)-(-)-1-(4-pyridyl)ethyl 1-adamantanecarboxylate
-
at 1.8 nM 50% C17,20-lyase inhibition, at 3.3 nM 50% 17alpha-hydroxylase inhibition
(S)-orteronel
three times more inhibitory toward the conversion of 17alpha-hydroxypregnenolone to dehydroepiandrosterone than toward the 17alpha-hydroxylation of pregnenolone. The (S)-enantiomer of orteronel is more inhibitory than the (R) enantiomer
1-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)-1H-imidazole
-
-
1-((4-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-methyl)-1H-imidazole
-
19% inhibition at 200 nM and 74% inhibition at 0.002 mM
1-((9H-fluoren-2-yl)ethyl)-1H-imidazole
-
-
1-((9H-fluoren-2-yl)methyl)-1H-imidazole
-
-
1-(1-(4'-(methylsulfanyl)biphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4'-(trifluoromethoxy)biphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4'-ethylbiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4'-fluorobiphenyl-4-yl)allyl)-1H-imidazole
-
-
1-(1-(4'-methylbiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(1-(4-(benzo[b]thiophen-5-yl)phenyl)propyl)-1H-imidazole
-
21% inhibition at 200 nM and 75% inhibition at 0.002 mM
1-(1-(4-(naphthalen-2-yl)phenyl)propyl)-1H-imidazole
-
-
1-(1-(4-thiophen-3-yl-phenyl)ethyl)-1H-imidazole
-
-
1-(1-(4-thiophen-3-yl-phenyl)propyl)-1H-imidazole
-
-
1-(1-(biphenyl-4-yl)allyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2,2-dimethyl-propyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2-methyl-propyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2-phenyl-ethyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-2-phenyl-methyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-3-methyl-butyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-butyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-cyclohexyl-methyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-pentyl)-1H-imidazole
-
-
1-(1-biphenyl-4-yl-propyl)-1H-imidazole
-
-
1-(1-bis-biphenyl-4-yl-methyl)-1H-imidazole
-
-
1-(1-[4-[5-(methylsulfanyl)thiophen-2-yl]phenyl]propyl)-1H-imidazole
-
-
1-(10-phenyl-decyl)-1H-imidazole
-
65.2% inhibition at 0.01 mM
1-(10-phenyldecyl)-1H-1,2,4-triazole
-
79.6% inhibition at 0.1 mM
1-(1H-imidazol-4-yl)-1-(4'-methoxy-[1,10-biphenyl]-3-yl)-2-methyl-1-propanol
1-(1H-imidazol-4-yl)-1-(4'-methoxy[1,1'-biphenyl]-4-yl)-2-methyl-1-propanol
1-(1H-imidazol-4-yl)-2-methyl-1-[4-(2-pyridinyl)phenyl]-1-propanol
1-(1H-imidazol-5-yl)-2-methyl-1-(4-thiophen-3-ylphenyl)propan-1-ol
-
-
1-(2-(4'-fluorobiphenyl-4-yl)propan-2-yl)-1H-imidazole
-
-
1-(2-phenyl-ethyl)-1H-imidazole
-
10.6% inhibition at 0.01 mM
1-(2-phenylethyl)-1H-1,2,4-triazole
-
10.9% inhibition at 0.1 mM
1-(3,4-dichlorobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0122 mM, of 17,20-lyase activity at 0.0021 mM
1-(3,5-dibromobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0259 mM, of 17,20-lyase activity at 0.00316 mM
1-(3,5-dichlorobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0226 mM, of 17,20-lyase activity at 0.0033 mM
1-(3-(4'-fluorobiphenyl-4-yl)pentan-3-yl)-1H-imidazole
-
-
1-(3-(4-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)phenyl)pentan-3-yl)-1H-imidazole
-
-
1-(3-chloro-1-(4'-fluorobiphenyl-4-yl)propyl)-1H-imidazole
-
-
1-(3-phenyl-propyl)-1H-imidazole
-
23.4% inhibition at 0.01 mM
1-(3-phenylpropyl)-1H-1,2,4-triazole
-
17.2% inhibition at 0.1 mM
1-(4'-chloro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
1-(4'-chloro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
1-(4'-fluoro[1,1'-biphenyl]-3-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
1-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
1-(4-(6-methoxynaphthalen-2-yl)phenyl)propan-1-ol
-
7% inhibition at 200 nM and 43% inhibition at 0.002 mM
1-(4-(benzofuran-5-yl)benzyl)-1H-imidazole
-
no inhibition at 200 nM and 21% inhibition at 0.002 mM
1-(4-bromobenzyl)-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0165 mM, of 17,20-lyase activity at 0.0028 mM
1-(4-chlorobenzyl)-1H-imidazole
1-(4-fluorobenzyl)-1H-imidazole
-
-
1-(4-furan-3-ylbenzyl)-1H-imidazole
-
-
1-(4-iodobenzyl)-1H-imidazole
1-(4-methylbenzyl)-1H-imidazole
-
-
1-(4-nitrobenzyl)-1H-imidazole
1-(4-phenyl-butyl)-1H-imidazole
-
40.7% inhibition at 0.01 mM
1-(4-phenylbutyl)-1H-1,2,4-triazole
-
29% inhibition at 0.1 mM
1-(5-phenyl-pentyl)-1H-imidazole
-
59.7% inhibition at 0.01 mM
1-(5-phenylpentyl)-1H-1,2,4-triazole
-
55% inhibition at 0.1 mM
1-(6-phenyl-hexyl)-1H-imidazole
-
61.3% inhibition at 0.01 mM
1-(6-phenylhexyl)-1H-1,2,4-triazole
-
60.4% inhibition at 0.1 mM
1-(7-phenyl-heptyl)-1H-imidazole
-
67.5% inhibition at 0.01 mM
1-(7-phenylheptyl)-1H-1,2,4-triazole
-
73.2% inhibition at 0.1 mM
1-(8-phenyl-octyl)-1H-imidazole
-
70.2% inhibition at 0.01 mM
1-(8-phenyloctyl)-1H-1,2,4-triazole
-
76.6% inhibition at 0.1 mM
1-(9-phenyl-nonyl)-1H-imidazole
-
64.5% inhibition at 0.01 mM
1-(9-phenylnonyl)-1H-1,2,4-triazole
-
79.1% inhibition at 0.1 mM
1-(bis-biphenyl-4-yl-methyl)-1H-imidazole
-
-
1-(imidazol-1-ylmethyl)-4-bromo-9H-9-xanthenone
-
at 0.0025 mM 98% inhibition
1-(imidazol-1-ylmethyl)-4-nitro-9H-9-xanthenone
-
at 0.0025 mM 94% inhibition
1-(imidazol-1-ylmethyl)-9-oxo-9H-4-xanthenecarbonitrile
-
at 0.0025 mM 92% inhibition
1-benzyl-1H-1,2,4-triazole
-
6.8% inhibition at 0.1 mM
1-benzyl-1H-imidazole
1-chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
1-[(4-phenylthiophen-2-yl)methyl]-1H-imidazole
-
-
1-[(5,7-dibromobenzofuran-2-yl)methyl]imidazole
1-[(5,7-dichlorobenzofuran-2-yl)methyl]imidazole
1-[(5-bromobenzofuran-2-yl)methyl]imidazole
1-[(5-chlorobenzofuran-2-yl)methyl]imidazole
1-[1,1'-biphenyl]-3-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
1-[1,1'-biphenyl]-4-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol
1-[1-(3',4'-dimethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(3'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
-
-
1-[1-(3'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4'-ethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4'-fluoro-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4'-fluoro-biphenyl-4-yl)propyl]-1H-imidazole
-
-
1-[1-(4'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
-
-
1-[1-(4'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
-
1-[1-(4-thiophen-3-ylphenyl)ethyl]-1H-imidazole
-
-
1-[1-(4-thiophen-3-ylphenyl)propyl]-1H-imidazole
-
-
1-[1-(7-fluoro-9H-fluoren-2-yl)-ethyl]-1H-imidazole
-
-
1-[1-(7-fluoro-9H-fluoren-2-yl)ethyl]-1H-imidazole
-
-
1-[1-[2-fluoro-4-(4-methylthiophen-3-yl)phenyl]propyl]-1H-imidazole
-
-
1-[1-[4-(2-chlorothiophen-3-yl)phenyl]propyl]-1H-imidazole
-
-
1-[1-[4-(3,4-difluorophenyl)thiophen-2-yl]propyl]-1H-imidazole
-
-
1-[1-[4-(4-methylthiophen-3-yl)phenyl]propyl]-1H-imidazole
-
-
1-[3-(4-bromophenyl)propyl]-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.00295 mM, of 17,20-lyase activity at 0.00033 mM
1-[3-(4-chlorophenyl)propyl]-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.0058 mM, of 17,20-lyase activity at 0.00055 mM
1-[3-(4-fluorophenyl)propyl]-1H-imidazole
-
50% inhibition of hydroxylase activity at 0.02781 mM, of 17,20-lyase activity at 0.00196 mM
1-[4-(1H-imidazol-1-ylmethyl)phenyl]methanimine
-
-
1-[4-(4-methylthiophen-3-yl)benzyl]-1H-imidazole
-
-
1-[4-(4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl)piperazin-1-yl]ethanone
-
-
1-[4-[5-(methylsulfanyl)thiophen-2-yl]benzyl]-1H-imidazole
-
-
1-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-1-ethanone
1-[[4-(3,4-difluorophenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(3,4-dimethoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(3-methoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(4-fluorophenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
1-[[4-(4-methoxyphenyl)thiophen-2-yl]methyl]-1H-imidazole
-
-
17(E)-picolinyliden-androst-4-en-3-one
-
complete inhibition at 0.05 mM
17(E)-picolinyliden-androst-4-en-3beta-ol
-
52% inhibition at 0.05 mM
17(E)-picolinyliden-androst-5-en-3beta-ol
-
55% inhibition at 0.05 mM
17-((1-(2-(trifluoromethyl)-1H-benzimidazol-5-yl)imino)ethyl)-5-androsten-3beta-ol
-
78.61% inhibition at 0.01 mM
17-((1-(6-methoxybenzothiazol-2-yl)imino)ethyl)-5-androsten-3beta-ol
-
81.99% inhibition at 0.01 mM
17-(1-(n-hexylamino)-1-hydroxyethyl)-5-androsten-3beta-ol
-
62.52% inhibition at 0.01 mM
17-(1H-1,2,3-triazol-1-yl)androsta-4,16-dien-3-one
17-(1H-1,2,4-triazol-1-yl)androsta-4,16-dien-3-one
17-(1H-imidazol-1-yl)androsta-4,16-dien-3-one
17-(2-amino-4-thiazolyl)-androsta-5,16-dien-3beta-ol
-
type II competitive inhibitor
17-(3'-pyrazolyl)androsta-4,16-dien-3beta-one
17-(3'-pyrazolyl)androsta-5,16-dien-3beta-ol
17-(3-pyridyl)-5alpha-androst-16-en-3-one
-
at 3 nM 50% inhibition of C17,20-lyase and at 4.7 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)-5alpha-androst-16-en-3alpha-ol
-
at 2.5 nM 50% inhibition of C17,20-lyase and at 4.3 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)-androst-5-en-3beta-ol
-
at 23 nM 50% inhibition of C17,20-lyase and at 47 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)-androsta-4,16-dien-3,11-dione
-
at 2.9 nM 50% inhibition of C17,20-lyase and at 13 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)androsta-3,5,16-triene
-
at 5.6 nM 50% inhibition of C17,20-lyase and at 12.5 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)androsta-4,16-dien-3-one
-
at 2.1 nM 50% inhibition of C17,20-lyase and at 2.8 nM 50% inhibition of 17alpha-hydroxylase activity
17-(3-pyridyl)androsta-5,6-dien-3beta-ol
17-(3-pyridyl)estra-1,3,5[10],16-tetraen-3-ol
-
at 1.8 nM 50% inhibition of C17,20-lyase and at 2.6 nM 50% inhibition of 17alpha-hydroxylase activity
17-(5'-isooxazoloyl)androsta-4,16-dien-3-one
17-(methylthio)androst-5-en-3beta-ol S-oxide
-
type I competitive inhibitor
17-hydroxypregnenolone
competitive inhibitor of 17alpha-hydrolase activity
17alpha-Hydroxy-4-androsten-3-one
-
competitive inhibitor of 17alpha-hydroxylation of pregnenolone and of the subsequent C17,20-side chain cleavage reaction
17alpha-picolyl-androst-4-en-3beta,17beta-diol
-
10% inhibition at 0.05 mM
17alpha-picolyl-androst-5-en-3beta,17beta-diol
-
5% inhibition at 0.05 mM
17beta-(1-p-chlorophenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-chlorophenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-chlorophenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-chlorophenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-cyanophenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-cyanophenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-cyanophenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-methoxyphenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-methoxyphenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-methoxyphenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-methoxyphenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-tolyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-tolyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-p-tolylphenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-p-tolylphenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-phenyl-3-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-phenyl-3-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(1-phenyl-5-pyrazolyl)androst-4-en-3-one
-
-
17beta-(1-phenyl-5-pyrazolyl)androst-5-en-3beta-ol
-
-
17beta-(cyclopropylamino)-androst-5-en-3beta-ol
-
mechanism-based inhibitor, irreversible inhibition
17beta-acetamidoandrost-4-en-3-one
-
-
17beta-hydroxy-17alpha-picolyl-androst-4-en-3-one
-
13% inhibition at 0.05 mM
17beta-ureidoandrosta-1,4-dien-3-one
-
-
19-azido-androstenedione
-
-
19-thiomethyl-androstenedione
-
-
2'-[[(E)-3-oxoandrost-4-en-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
1 microM, 54% inhibition
2'-[[(E)-3beta-hydroxyandrost-5-en-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
1 microM, 78% inhibition
2'-[[(E)-6-oxo-3alpha,5alpha-cycloandrostan-17-ylidene]methyl]-4',5'-dihydro-1',3'-oxazole
compound strongly depresses electrocatalytic activity of CYP17A1 toward pregnenolone at concentrations of 0.1 microM and 1 microM, but data do not obey the Michaelis-Menten catalytic model
2-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzamide
-
39.38% inhibition at 0.01 mM
2-(1-(1H-imidazol-1-yl)ethyl)-7-fluoro-9H-carbazole
-
-
2-(1-imidazol-1-yl-ethyl)-9H-carbazole
-
-
2-(1H-imidazol-4-ylmethyl)-9H-carbazole
-
suicide inhibitor
2-(4-pyridyl)propan-2-yl 1-adamantanecarboxylate
-
at 2.7 nM 50% C17,20-lyase inhibition, at 8.8 nM 50% 17alpha-hydroxylase inhibition
2-(chloromethyl)-5-[4-(1H-imidazol-1-ylmethyl)phenyl]pyridine
-
-
2-fluoro-4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)phenol hydrobromide
-
-
2-fluoro-4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)phenol hydrobromide
-
-
2-fluoro-4-[5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]phenol
-
-
2-fluoro-4-[5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl]phenol
-
-
2-fluoro-5-[4-(1H-imidazol-1-ylmethyl)phenyl]pyridine
-
-
20(S)-20,21-aziridinylpregn-5-en-3beta-ol
-
type II competitive inhibitor
20-hydroxyiminopregna-4,14,16-trien-3-one
-
at 0.0002 mM 50% inhibition
20-hydroxyiminopregna-4,16-dien-3-one
-
at 0.0001 mM 50% inhibition
20-hydroxyiminopregna-5,14,16-trien-3beta-ol
-
at 0.0002 mM 50% inhibition
20-hydroxyiminopregna-5,16-dien-3beta-ol
-
at 0.00017 mM 50% inhibition
20xi-hydroxy-21-trifluoropregn-4-en-3-one
21-hydroxyimino-21-methylpregn-4-en-3-one
-
at 0.0036 mM 50% inhibition
21-hydroxyiminopregn-4-en-3-one
21-hydroxyiminopregn-5-en-3beta-ol
21-hydroxyiminopregna-4,17(20)-dien-3-one
21-hydroxyiminopregna-5,17(29)-dien-3beta-ol
21-methylpregn-5-en-3beta-ol-21-one
-
at 0.0098 mM 50% inhibition
21-trifluoropregn-4-en-3,20-dione
-
at 0.0021 mM 50% inhibition
21-trifluoropregn-5-en-3beta,20xi-diol
-
at 0.0044 mM 50% inhibition
22-Amino-23,24-bisnor-5-cholen-3beta-ol
-
type II competitive inhibitor
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
-
3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
3,5,4'-triacetylresveratrol
-
3,5,4'-trimethylresveratrol
inhibition by is more selective on the 17,20-lyase activity than hydroxylase activity of CYP17A1
3,5-diacetylresveratrol
-
3,5-dihydroxy-4-[([[(3alpha)-3-methyl-20-oxopregn-5-en-3-yl]oxy]carbonyl)oxy]benzoic acid
-
83.21% inhibition at 0.01 mM
3-(4'-fluorobiphenyl-4-yl)-3-(1H-imidazol-1-yl)propan-1-ol
-
-
3-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
-
-
3-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
3-(6-Chloro-3-methyl-2-indenyl)pyridine
-
competitive inhibitor
3-chloro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
3-pyridyl-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene
-
suicide inhibitor
3-[4-(1H-imidazol-1-ylmethyl)phenyl]pyridine
-
-
3-[5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]pyridine
-
-
3-[6-(4-fluorophenyl)-1H-inden-3-yl]pyridine
-
-
3beta-acetoxy-17-(3-pyridyl)androsta-5,16-diene
-
at 17 nM 50% inhibition of C17,20-lyase and at 18 nM 50% inhibition of 17alpha-hydroxylase activity
3beta-hydroxy-17-(1H-1,2,3-triazol-1-yl)androsta-5,16-diene
3beta-hydroxy-17-(1H-1,2,4-triazol-1-yl)androsta-5,16-diene
3beta-hydroxy-17-(1H-imidazol-1-yl)androsta-5,16-diene
3beta-hydroxy-23,24-bisnor-5-cholenic-hydroxamic acid
3beta-hydroxy-5-androsten-17beta-hydroxamic acid
4'-(1-(1H-imidazol-1-yl)propyl)biphenyl-4-carbonitrile
-
-
4'-(1-imidazol-1-yl-propyl)-3,5-dimethyl-biphenyl-4-ol
-
-
4'-(1-imidazol-1-yl-propyl)-3-methyl-biphenyl-4-ol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-3,5-diol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-3-ol
-
-
4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
4'-(1H -imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-ol
-
-
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-carboxamide
4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl[1,1'-biphenyl]-3-sulfonamide
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-3-methoxybenzoic acid
-
43.34% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
-
56.23% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(isoxazol-3-yl)benzenesulfonamide
-
81.78% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide
-
16.27% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzenesulfonamide
-
57.1% inhibition at 0.01 mM; 78.84% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzenesulfonic acid
-
8.37% inhibition at 0.01 mM
4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzoic acid
-
49.21% inhibition at 0.01 mM
4-(1H-imidazol-1-ylmethyl)-7-[(3-methylbenzyl)oxy]-2H-chromen-2-one
-
-
4-(1H-imidazol-1-ylmethyl)-7-[[3-(trifluoromethyl)benzyl]oxy]-2Hchromen-2-one
-
-
4-(1H-imidazol-1-ylmethyl)phenol
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-(trifluoromethyl)benzenesulfonate
4-(1H-imidazol-1-ylmethyl)phenyl 4-bromobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-butylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-chlorobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-ethylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-fluorobenzenesulfonate
4-(1H-imidazol-1-ylmethyl)phenyl 4-iodobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-methoxybenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-methylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-nitrobenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-pentylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl 4-propylbenzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl benzenesulfonate
-
-
4-(1H-imidazol-1-ylmethyl)phenyl biphenyl-4-sulfonate
-
-
4-(5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)pyridine hydrochloride
-
-
4-(5-(4-fluorophenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
4-(5-(4-methoxyphenyl)-3H-inden-1-yl)pyridine hydrochloride
-
-
4-(5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
-
-
4-(5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl)benzene-1,2-diol hydrobromide
-
-
4-(6-(3,4-difluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(6-(3,4-difluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(6-(4-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(6-(4-fluorophenyl)-3,4-dihydronaphthalen-1-yl)pyridine hydrochloride
-
-
4-(8-(1-(1H-imidazol-1-yl)propyl)quinolin-5-yl)phenol
-
17% inhibition at 200 nM and 71% inhibition at 0.002 mM
4-(benzo[b]thiophen-5-yl)benzaldehyde
-
7% inhibition at 200 nM and 40% inhibition at 0.002 mM
4-amino-17beta-(cyclopropylamino)-androst-4-en-3-one
-
suicide inhibitor
4-amino-17beta-(cyclopropyloxy)-androst-4,6-dien-3-one
-
suicide inhibitor
4-amino-17beta-(cyclopropyloxy)-androst-4-en-3-one
-
suicide inhibitor
4-chloro-3,4-dihydro-2-(3-pyridyl)-1-(2H)-naphthalenone
-
competitive inhibitor
4-hydroxybenzyl imidazole
4-iodobenzyl imidazole
-
-
4-pyridylmethyl 1-adamantanecarboxylate
-
at 18 nM 50% C17,20-lyase inhibition, at 43 nM 50% 17alpha-hydroxylase inhibition
4-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-morpholine
-
-
4-[4-[1-(1H-imidazol-1-yl)ethyl]phenyl]morpholine
-
-
4-[5-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl]pyridine
-
-
4-[5-(pyridin-4-yl)-5,6,7,8-tetrahydronaphthalen-2-yl]benzene-1,2-diol
-
-
4-[5-(pyridin-4-yl)-7,8-dihydronaphthalen-2-yl]benzene-1,2-diol
-
-
4-[6-(3,4-difluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]pyridine
-
-
4-[6-(3,4-difluorophenyl)-3,4-dihydronaphthalen-1-yl]pyridine
-
-
4-[6-(4-fluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]pyridine
-
-
4-[6-(4-fluorophenyl)-1H-inden-3-yl]pyridine
-
-
4-[6-(4-fluorophenyl)-3,4-dihydronaphthalen-1-yl]pyridine
-
-
4-[6-(4-methoxyphenyl)-1H-inden-3-yl]pyridine
-
-
5-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-(4-(1-(1H-imidazol-1-yl)propyl)phenyl)-1H-indole
-
5% inhibition at 200 nM and 27% inhibition at 0.002 mM
5-(4-(1H-imidazol-1-ylmethyl)phenyl)-1H-indole
-
5% inhibition at 200 nM and 39% inhibition at 0.002 mM
5-(4-fluorophenyl)-1-(pyridin-3-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-(4-fluorophenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-(4-methoxyphenyl)-1-(pyridin-4-yl)-2,3-dihydro-1H-inden-1-ol
-
-
5-[(3-chlorophenyl-1H-imidazole-1-yl)methyl]-1H-benzimidazole
-
suicide inhibitor
5-[4-(1H-imidazol-1-ylmethyl)phenyl]pyrimidine
-
-
6-(3,4-difluorophenyl)-1-(pyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3,4-difluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3-fluoro-4-methoxyphenyl)-1-(pyridin-3-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(3-fluoro-4-methoxyphenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-(4-(1H-imidazol-1-ylmethyl)phenyl)benzo[d]thiazole
-
no inhibition at 200 nM and 17% inhibition at 0.002 mM
6-(4-(3-(1H-imidazol-1-yl)pentan-3-yl)phenyl)naphthalen-2-ol
-
16% inhibition at 200 nM and 74% inhibition at 0.002 mM
6-(4-fluorophenyl)-1-(pyridin-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol
-
-
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2,3-dihydro-1H-benzo[f]isoindol-1-one
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-2,3-dihydro-1H-benzo[f]isoindol-1-one
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,1-dimethyl-2-naphthamide
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N,3-dimethyl-2-naphthamide
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-isopropyl-2-naphthamide
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-methyl-2-naphthamide
6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-N-propyl-2-naphthamide
7-(1-(1H-imidazol-1-yl)ethyl)-9H-fluoren-2-ol
-
-
7-[(3-chlorobenzyl)oxy]-4-(1H-imidazol-1-ylmethyl)-2H-chromen-2-one
-
-
7-[(3-fluorobenzyl)oxy]-4-(1H-imidazol-1-ylmethyl)-2H-chromen-2-one
-
-
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one
7-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-methyl-1,2-dihydro-3H-benzo[e]isoindol-3-one
abiraterone
abiraterone acetate
benzyl imidazole
-
-
CYP21
direct molecular interactions, with electrostatic interactions playing a crucial role, between steroidogenic enzymes CYP17 and CYP21, EC 1.14.99.10, that are localized in endoplasmic reticulum membranes of adrenal cortex and involved in biosynthesis of corticosteroid hormones. The interaction in vitro reduces the catalytic activities of both enzymes at high ionic strength, i.e. 300 mM NaCl, while it increases activity at low ionic strength, i.e. 100 mM NaCl, overview
-
cytochrome b5
-
supresses 17alpha-hydrolase and C17,20-lyase activity below pH 6.3-6.5
-
diethyl-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-amine
-
-
E-1-methyl-2-(1-hydroxyiminoethyl)-6-methoxy-3,4-dihydronaphthalene
-
at 0.0025 mM 7% inhibition
Emulgen 913
-
at 0.2% w/v 94% inhibition
estradiol-17beta
-
inhibits both and C17,20 lyase activity in testis and duodenum, competitive inhibitor
iodoacetate
-
at 1 mM 100% inhibition of 17alpha-hydroxylation and 50% inhibition of lyase activity
ketoconazole
methyl 6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthoate
N'-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]-N-methylurea
N-(4,6-dimethylpyrimidin-2-yl)-4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)benzene sulfonamide
-
48.37% inhibition at 0.01 mM
N-(4-((1-(5-androsten-3beta-ol-17-yl)ethylidene)amino)phenyl)acetamide
-
40.02% inhibition at 0.01 mM
N-ethyl-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthamide
N-[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-acetamide
-
-
N-[4'-[(1S)-1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]biphenyl-3-yl]acetamide
-
-
N-[4'-[1-hydroxy(1H-imidazol-4-yl)methyl][1,1'-biphenyl]-3-yl]acetamide
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]-N'-methylurea
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-3-yl]acetamide
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl][1,1'-biphenyl]-4-yl]acetamide
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)ethyl][1,1'-biphenyl]-3-yl]acetamide
N-[4'-[1-hydroxy-1-(1H-imidazol-4-yl)propyl][1,1'-biphenyl]-3-yl]acetamide
N-[4'-[cyclopropyl(hydroxy)-1H-imidazol-4-ylmethyl][1,1'-biphenyl]-3-yl]acetamide
N-[6-(4-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]phenyl)-2-pyridyl]acetamide
N-[6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl]-2-naphthyl]acetamide
nitrogen
-
complete inhibition
p-chloromercuribenzoate
-
at 1 mM complete inhibition
pregnenolone
-
-
progesterone
-
-
resveratrol
i.e. trans-3,5,4'-trihydroxystilbene
siRNA
-
siRNA targeting the CYP17 gene
-
sodium cholate
sulfamerazine
-
53.44% inhibition at 0.01 mM
sulfamethazine
-
49.34% inhibition at 0.01 mM
sulfamethoxazole
-
55.23% inhibition at 0.01 mM
TOK-001
toluene-4-sulfonic acid 4-imidazol-1-ylmethyl-phenyl ester
-
-
transforming growth factor-beta1
-
inhibits 17alpha-hydroxylation in vitro by a noncompetitive mechanism
-
VN/124-1
-
a 17alpha-hydroxylase/17,20 lyase inhibitor, is cytotoxic in prostate cancer cells and synergistically induces endoplasmic reticulum stress, mechanism, overview
VN/85-1
-
-
YM-116
Z-1-methyl-2-(1-hydroxyiminoethyl)-6-methoxy-3,4-dihydronaphthalene
-
at 0.0025 mM 5% inhibition
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-carbamic acid tert-butyl ester
-
-
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethyl-amine
-
-
[4'-(1H-imidazol-1-yl-propyl)-biphenyl-4-yl]-dimethylamine
-
-
additional information
-