3471. Dutasteride
Nomenclature
CAS number: 164656-23-9
(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; 17β-N-[2,5-Bis(trifluoromethyl)phenyl]carbamoyl-4-aza-5α-androst-1-en-3-one; GG-745; GI-198745; Avodart (GSK); Avolve (GSK). C27H30F6N2O2; mol wt 528.53.
C 61.36%, H 5.72%, F 21.57%, N 5.30%, O 6.05%.
Description and references
Dual inhibitor of 5α-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°.Therapeutic Category
In treatment of benign prostatic hyperplasia.
Keywords
5α-Reductase Inhibitor; Antiprostatic Hypertrophy