440. Aminoglutethimide

Nomenclature

CAS number: 125-84-8
3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione; 2-(p-aminophenyl)-2-ethylglutarimide; 3-ethyl-3-(p-aminophenyl)-2,6-dioxopiperidine; Cytadren (Novartis); Orimeten (Novartis).
C13H16N2O2; mol wt 232.28.
C 67.22%, H 6.94%, N 12.06%, O 13.78%.

Description and references

Aromatase inhibitor; also blocks adrenal steroidogenesis. Formerly used as anticonvulsant. Prepn: K. Hoffmann, E. Urech, US 2848455 (1958 to Ciba). Mass spectrum: G. Ruecker, G. Bohn, Arch. Pharm. 302, 204 (1969). Resolution and abs config of antipodes: N. Finch et al., Experientia 31, 1002 (1975). Comprehensive description: H. Y. Aboul-Enein, Anal. Profiles Drug Subs. 15, 35-69 (1986). Review of pharmacology and clinical use in Cushing's disease and breast cancer: R. J. Santen, R. I. Misbin, Pharmacotherapy 1, 95-120 (1981); in prostate cancer: K. A. Havlin, D. L. Trump, Cancer Treat. Res. 39, 83-96 (1988).

Chemical structure

Properties

Crystals from methanol or ethyl acetate, mp 149-150°. Readily sol in most organic solvents. Poorly sol in ethyl acetate, 0.1N HCl, absolute ethanol. Practically insol in water.

Therapeutic Category

Adrenocortical suppressant; antineoplastic.

Keywords

Anticonvulsant; Antineoplastic (Hormonal); Antiadrenals; Aromatase Inhibitors; Aromatase Inhibitors; Adrenocortical Suppressant