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Literature summary extracted from

  • Hille, U.E.; Hu, Q.; Vock, C.; Negri, M.; Bartels, M.; Mueller-Vieira, U.; Lauterbach, T.; Hartmann, R.W.
    Novel CYP17 inhibitors: synthesis, biological evaluation, structure-activity relationships and modelling of methoxy- and hydroxy-substituted methyleneimidazolyl biphenyls (2009), Eur. J. Med. Chem., 44, 2765-2775.
    View publication on PubMed

Application

EC Number Application Comment Organism
1.14.14.19 drug development CYP17 is a target for inhibitor design as a target in treatment of prostate cancer Homo sapiens

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.14.19 CYP17, expression in Escherichia coli, co-expression with NADPH-P450 reductase Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.14.19 1-[1-(3',4'-dimethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
Homo sapiens
1.14.14.19 1-[1-(3'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
-
Homo sapiens
1.14.14.19 1-[1-(3'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
Homo sapiens
1.14.14.19 1-[1-(4'-ethoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
Homo sapiens
1.14.14.19 1-[1-(4'-methoxy-biphenyl-4-yl)-ethyl]-1H-imidazole
-
Homo sapiens
1.14.14.19 1-[1-(4'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
-
Homo sapiens
1.14.14.19 3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
Homo sapiens
1.14.14.19 3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
Homo sapiens
1.14.14.19 3-chloro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
Homo sapiens
1.14.14.19 4'-(1-imidazol-1-yl-propyl)-3,5-dimethyl-biphenyl-4-ol
-
Homo sapiens
1.14.14.19 4'-(1-imidazol-1-yl-propyl)-3-methyl-biphenyl-4-ol
-
Homo sapiens
1.14.14.19 4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
-
Homo sapiens
1.14.14.19 4'-(1-imidazol-1-yl-propyl)-biphenyl-3,5-diol
-
Homo sapiens
1.14.14.19 4'-(1-imidazol-1-yl-propyl)-biphenyl-3-ol
-
Homo sapiens
1.14.14.19 4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
-
Homo sapiens
1.14.14.19 abiraterone
-
Homo sapiens
1.14.14.19 ketoconazole unspecific inhibitor Homo sapiens
1.14.14.19 additional information inhibitor design and synthesis via Suzuki-cross-coupling, Grignard reaction and CDI-assisted SNt-reaction with imidazole, overview Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.14.19 additional information Homo sapiens CYP17 is the cytochrome b5 modulated key enzyme for the biosynthesis of androgens, catalyzing the 17alpha-hydroxylation of pregnenolone and progesterone and the subsequent cleavage of the C 20,21-acetyl group to yield the corresponding androgens dehydroepiandrosterone and androstendione ?
-
?
1.14.14.19 pregnenolone + ferrocytochrome b5 + O2 Homo sapiens
-
?
-
?
1.14.14.19 progesterone + ferrocytochrome b5 + O2 Homo sapiens
-
?
-
?

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.19 Homo sapiens
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.14.14.19 adrenal gland
-
Homo sapiens
-
1.14.14.19 testis
-
Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.19 additional information CYP17 is the cytochrome b5 modulated key enzyme for the biosynthesis of androgens, catalyzing the 17alpha-hydroxylation of pregnenolone and progesterone and the subsequent cleavage of the C 20,21-acetyl group to yield the corresponding androgens dehydroepiandrosterone and androstendione Homo sapiens ?
-
?
1.14.14.19 pregnenolone + ferrocytochrome b5 + O2
-
Homo sapiens ?
-
?
1.14.14.19 progesterone + ferrocytochrome b5 + O2
-
Homo sapiens ?
-
?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.19 17alpha-hydroxylase-17,20-lyase
-
Homo sapiens
1.14.14.19 CYP17
-
Homo sapiens

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.14.19 ferrocytochrome b5
-
Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.14.19 0.000052
-
-
Homo sapiens 3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
1.14.14.19 0.000072
-
-
Homo sapiens abiraterone
1.14.14.19 0.00009
-
-
Homo sapiens 3'-fluoro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
1.14.14.19 0.000152
-
-
Homo sapiens 4'-(1-imidazol-1-yl-propyl)-biphenyl-3,4-diol
1.14.14.19 0.000164
-
-
Homo sapiens 4'-(1-imidazol-1-yl-propyl)-biphenyl-3-ol
1.14.14.19 0.000188
-
-
Homo sapiens 1-[1-(3'-methoxy-biphenyl-4-yl)-propyl]-1H-imidazole
1.14.14.19 0.000195
-
-
Homo sapiens 4'-(1-imidazol-1-yl-propyl)-biphenyl-3,5-diol
1.14.14.19 0.000217
-
-
Homo sapiens 3-chloro-4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
1.14.14.19 0.000231
-
-
Homo sapiens 4'-(1-imidazol-1-yl-propyl)-biphenyl-4-ol
1.14.14.19 0.000261
-
-
Homo sapiens 4'-(1-imidazol-1-yl-propyl)-3-methyl-biphenyl-4-ol
1.14.14.19 0.000379
-
-
Homo sapiens 4'-(1-imidazol-1-yl-propyl)-3,5-dimethyl-biphenyl-4-ol
1.14.14.19 0.00278
-
-
Homo sapiens ketoconazole

General Information

EC Number General Information Comment Organism
1.14.14.19 metabolism CYP17 catalyzes the last step in androgen biosynthesis Homo sapiens