Title: Trilostane
CAS Registry Number: 13647-35-3
CAS Name: (4a,5a,17b)-4,5-Epoxy-3,17-dihydroxyandrost-2-ene-2-carbonitrile
Additional Names: 4,5-epoxy-17-hydroxy-3-oxoandrostane-2-carbonitrile; 2a-cyano-4a,5a-epoxyandrostan-17b-ol-3-one
Manufacturers' Codes: Win-24540
Trademarks: Desopan (Mochida); Modrastane (Winthrop); Modrenal (Winthrop)
Molecular Formula: C20H27NO3
Molecular Weight: 329.43
Percent Composition: C 72.92%, H 8.26%, N 4.25%, O 14.57%
Literature References: Prepn: R. O. Clinton, A. J. Manson, US 3296255 (1967 to Sterling); H. C. Neumann et al., J. Med. Chem. 13, 948 (1970). Inhibition of steroid biosynthesis: G. O. Potts et al., Steroids 32, 257 (1978). Disposition in animals: J. F. Baker et al., Arch. Int. Pharmacodyn. Ther. 243, 4 (1980). Metabolism in rats: Y. Mori et al., Chem. Pharm. Bull. 29, 2646 (1981); in humans: D. T. Robinson et al., J. Steroid Biochem. 21, 601 (1984). HPLC determn in plasma: P. Powles et al., J. Chromatogr. 311, 434 (1984); and of major metabolite, 17-ketotrilostane: R. R. Brown et al., ibid. 339, 440 (1985). Clinical study in Cushing's syndrome: P. Komanicky et al., J. Clin. Endocrinol. Metab. 47, 1042 (1978). Clinical trials in breast cancer: C. G. Beardwell et al., Cancer Chemother. Pharmacol. 10, 158 (1983); C. J. Williams et al., Cancer Treat. Rep. 71, 1197 (1987).
Properties: Tan crystals from pyridine/dioxane, mp 257.8-270° (dec). [a]D25 +137.4° (c = 1 in pyridine). uv max (ethanol): 252 nm (e 8300).
Melting point: mp 257.8-270° (dec)
Optical Rotation: [a]D25 +137.4° (c = 1 in pyridine)
Absorption maximum: uv max (ethanol): 252 nm (e 8300)
Therap-Cat: Adrenocortical suppressant; in treatment of breast cancer.
Keywords: Adrenocortical Suppressant; Antineoplastic (Hormonal); Antiadrenals. |