1200. Bicalutamide

Nomenclature

CAS number: 90357-06-5
N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide; 4-cyano-3-trifluoromethyl-N-(3-p-fluorophenylsulfonyl-2-hydroxy-2-methylpropionyl)aniline; (±)-4′-cyano-α,α,α-trifluoro-3-[(p-fluorophenyl)sulfonyl]-2-methyl-m-lactotoluidide; ICI-176334; Casodex (AstraZeneca).
C18H14F4N2O4S; mol wt 430.37.
C 50.23%, H 3.28%, F 17.66%, N 6.51%, O 14.87%, S 7.45%.

Description and references

Non-steroidal peripherally active antiandrogen. Prepn: H. Tucker, EP 100172; idem, US 4636505 (1984, 1987 both to ICI); and structure-activity: H. Tucker et al., J. Med. Chem. 31, 954 (1988). Resolution and activity of enantiomers: H. Tucker, G. J. Chesterson, ibid. 885. Pharmacokinetics: I. D. Cockshott et al., Eur. Urol. 18, Suppl. 3, 10 (1990). Clinical trials in prostate cancer: G. Lunglmayr, Horm. Res. 32, Suppl. 1, 77 (1989); D. W. W. Newling, Eur. Urol. 18 Suppl. 3, 18 (1990). Review of pharmacology: B. J. A. Furr in Hormonal Therapy of Prostatic Diseases: Basic and Clinical Aspects, M. Motta, M. Serio, Eds. (Mediocom Europe, Milan, 1987) 148-161.

Chemical structure

Properties

Crystals from a 1:1 (v/v) mix of ethyl acetate and petroleum ether, mp 191-193°.

Therapeutic Category

Antiandrogen; antineoplastic (hormonal).

Keywords

Antiandrogen; Antineoplastic (Hormonal); Antiandrogens