4082. Finasteride

Nomenclature

CAS number: 98319-26-7
(4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(1,1-Dimethylethyl)-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-tert-butylcarbamoyl)-4-aza-5α-androst-1-en-3-one; (5α,17β)-N-(1,1-dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide; MK-906; Chibro-Proscar (Chibret); Finastid (Neopharmed); Propecia (Merck & Co.); Proscar (Merck & Co.); Prostide (Sigma-Tau).
C23H36N2O2; mol wt 372.54.
C 74.15%, H 9.74%, N 7.52%, O 8.59%.

Description and references

Inhibitor of 5α-reductase, the enzyme which converts testosterone to the more potent androgen, 5α-dihydrotestosterone. Prepn: G. H. Rasmusson, G. F. Reynolds, EP 155096; eidem, US 4760071 (1985, 1988 both to Merck & Co.); G. H. Rasmusson et al., J. Med. Chem. 29, 2298 (1986); A. Bhattacharya et al., J. Am. Chem. Soc. 110, 3318 (1988). HPLC determn in plasma and urine: J. R. Carlin et al., J. Chromatogr. 427, 79 (1988). Review of pharmacology and clinical uses: S. L. Sudduth, M. J. Koronkowski, Pharmacotherapy 13, 309-329 (1993). Clinical trials in benign prostatic hyperplasia: J. L. Tenover et al., Clin. Ther. 19, 243 (1997); J. D. McConnell et al., N. Engl. J. Med. 338, 557 (1998); in male pattern hair loss: K. D. Kaufman et al., J. Am. Acad. Dermatol. 39, 578 (1998). Review of use in benign prostatic hyperplasia: J. E. Edwards, R. A. Moore, BMC Urol. 2, 14 (2002); in alopecia: J. F. Libecco, W. F. Bergfeld, Expert Opin. Pharmacother. 5, 933-940 (2004); in prevention of prostate cancer: E. D. Canby-Hagino et al., ibid. 7, 899-905 (2006).

Chemical structure

Properties

White to off-white crystalline solid, mp ≈257° (dried to anhydrous under N2). Also reported as mp 252-254° (Rasmusson, 1988). [α]405 59° (c = 1 in methanol). Freely sol in chloroform, DMSO, ethanol, methanol, n-propanol; sparingly sol in propylene glycol, polyethylene glycol 400; very slightly sol in 0.1N HCl, 0.1N NaOH, water.

Therapeutic Category

In treatment of benign prostatic hypertrophy. Antialopecia agent.

Therapeutic Category (Veterinary)

In treatment of benign prostatic hypertrophy.

Keywords

Antialopecia Agent; Antiprostatic Hypertrophy; 5α-Reductase Inhibitor