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CHEBI:521033 - dutasteride

ChEBI IDCHEBI:521033
ChEBI Namedutasteride
Stars
DefinitionAn aza-steroid that is inasteride 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.
Last Modified16 May 2018
DownloadsMolfile
FormulaC27H30F6N2O2
Net Charge0
Average Mass528.537
Monoisotopic Mass528.22115
SMILES[H][C@@]12CC[C@@]3([H])NC(=O)C=C[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1([H])C(=O)Nc1cc(C(F)(F)F)ccc1C(F)(F)F
InChIInChI=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
InChIKeyJWJOTENAMICLJG-QWBYCMEYSA-N
Wikipedia
Roles Classification
Biological Role:
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-5α-steroid 4-dehydrogenase (NADP+), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5α-dihydrotestosterone.
Application:
antihyperplasia drug  A drug used for the treatment of hyperplasia (increaced cell production within an organ or tissue).
ChEBI Ontology
Outgoing Relation(s)
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 (trifluoromethyl)benzenes (CHEBI:83565)
dutasteride (CHEBI:521033) is a aza-steroid (CHEBI:35726)
dutasteride (CHEBI:521033) is a δ-lactam (CHEBI:77727)
IUPAC Name 
N-[2,5-bis(trifluoromethyl)phenyl]-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
Synonyms  Source
α,α,α,α',α',α'-hexafluoro-3-oxo-4-aza-5α-androst-1-ene-17β-carboxy-2',5'-xylidideChemIDplus
(5α,17β)-N-(2,5-bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamideChemIDplus
Manual XrefsDatabases
D03820KEGG DRUG
DB01126DrugBank
WO9507927Patent
DutasterideWikipedia
973DrugCentral
Registry NumbersSources
Beilstein:7401530Beilstein
CAS:164656-23-9ChemIDplus