CHEBI:521033 - dutasteride

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ChEBI Name dutasteride
ChEBI ID CHEBI:521033
Definition Finasteride in which the tert-butyl group is replaced by a 2,5-bis(trifluoromethyl)phenyl group. A synthetic 4-azasteroid, dutasteride is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5α-reductase, an intracellular enzyme that converts testosterone to 5α-dihydrotestosterone. Dutasteride is used for the treatment of symptomatic benign prostatic hyperplasia in men with an enlarged prostate gland.
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Formula C27H30F6N2O2
Net Charge 0
Average Mass 528.52970
Monoisotopic Mass 528.221
InChI InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1
InChIKey JWJOTENAMICLJG-QWBYCMEYSA-N
SMILES [H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@]([H])(C(=O)Nc5cc(ccc5C(F)(F)F)C(F)(F)F)[C@@]4(C)CC[C@]3([H])[C@@]1(C)C=CC(=O)N2
Roles Classification
Biological Role(s): EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor
An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP+), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.
Application(s): antihyperplasia drug
A drug used for the treatment of hyperplasia (increaced cell production within an organ or tissue).
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ChEBI Ontology
Outgoing dutasteride (CHEBI:521033) has parent hydride 5α-androstane (CHEBI:28859)
dutasteride (CHEBI:521033) has role antihyperplasia drug (CHEBI:59844)
dutasteride (CHEBI:521033) has role EC 1.3.1.22 [3-oxo-5α-steroid 4-dehydrogenase (NADP+)] inhibitor (CHEBI:50781)
dutasteride (CHEBI:521033) is a δ-lactam (CHEBI:77727)
dutasteride (CHEBI:521033) is a (trifluoromethyl)benzenes (CHEBI:83565)
dutasteride (CHEBI:521033) is a aza-steroid (CHEBI:35726)
IUPAC Name
N-[2,5-bis(trifluoromethyl)phenyl]-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
Synonyms Sources
(5α,17β)-N-(2,5-bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide ChemIDplus
α,α,α,α',α',α'-hexafluoro-3-oxo-4-aza-5α-androst-1-ene-17β-carboxy-2',5'-xylidide ChemIDplus
Database Links Databases
973 DrugCentral
D03820 KEGG DRUG
DB01126 DrugBank
Dutasteride Wikipedia
WO9507927 Patent
View more database links
Registry Numbers Types Sources
164656-23-9 CAS Registry Number ChemIDplus
7401530 Beilstein Registry Number Beilstein
Last Modified
22 February 2017