Dutasteride

Title: Dutasteride
CAS Registry Number: 164656-23-9
CAS Name: (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-[2,5-Bis(trifluoromethyl)phenyl]-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxamide
Additional Names: 17b-N-[2,5-Bis(trifluoromethyl)phenyl]carbamoyl-4-aza-5a-androst-1-en-3-one
Manufacturers' Codes: GG-745; GI-198745
Trademarks: Avodart (GSK); Avolve (GSK)
Molecular Formula: C27H30F6N2O2
Molecular Weight: 528.53
Percent Composition: C 61.36%, H 5.72%, F 21.57%, N 5.30%, O 6.05%
Literature References: Dual inhibitor of 5a-reductase isoenzymes types 1 and 2; structurally related to finasteride, q.v. Prepn: K. W. Batchelor, S. V. Frye, WO 9507927 (1995 to Glaxo). Structure-activity study: R. K. Bakshi et al., J. Med. Chem. 38, 3189 (1995). Clinical pharmacokinetics: P. O. Gisleskog et al., Br. J. Clin. Pharmacol. 47, 53 (1999). Clinical trial in benign prostatic hyperplasia: C. G. Roehrborn et al., Urology 60, 434 (2002). Review of discovery and development: S. V. Frye et al., Pharm. Biotechnol. 11, 393-422 (1998); of clinical experience: B. Djavan et al., Expert Opin. Pharmacother. 6, 311-317 (2005).
Properties: White crystalline solid, mp 245-245.5°.
Melting point: mp 245-245.5°
Therap-Cat: In treatment of benign prostatic hyperplasia.
Keywords: 5a-Reductase Inhibitor; Antiprostatic Hypertrophy.
Duthaler-Hafner Reagent d-Verbenone Dyclonine Dydrogesterone Dymanthine

Dutasteride
Systematic (IUPAC) name
(5α, 17β)-N-{2,5-bis(trifluoromethyl)phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide
Clinical data
Trade names Avodart
AHFS/Drugs.com monograph
MedlinePlus a603001
Pregnancy cat. X (US) Not to be handled by pregnant women
Legal status POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 60%
Protein binding 99%
Metabolism Hepatic (CYP3A4-mediated)
Half-life 5 weeks
Excretion Fecal
Identifiers
CAS number 164656-23-9 YesY
ATC code G04CB02
PubChem CID 6918296
DrugBank DB01126
ChemSpider 5293502 YesY
UNII O0J6XJN02I YesY
KEGG D03820 YesY
ChEBI CHEBI:521033 YesY
ChEMBL CHEMBL1200969 N
Chemical data
Formula C27H30F6N2O2 
Mol. mass 528.53 g/mol
 N (what is this?)  (verify)

Dutasteride (trademark name Avodart, manufactured by GlaxoSmithKline) is a dual 5-α reductase inhibitor that inhibits conversion of testosterone to dihydrotestosterone (DHT). Used for benign prostatic hyperplasia; however, it increases the risk of erectile dysfunction[1] and decreased sexual desire.[2]