2102. Chlormadinone Acetate

Nomenclature

CAS number: 302-22-7
17-(Acetyloxy)-6-chloropregna-4,6-diene-3,20-dione; 6-chloro-17-hydroxypregna-4,6-diene-3,20-dione acetate; 6-chloro-6-dehydro-17α-hydroxyprogesterone acetate; 6-chloro-6-dehydro-17α-acetoxyprogesterone; 17α-acetoxy-6-chloro-6,7-dehydroprogesterone; Chronosyn (Veterinaria); Cyclonorm (Streuli); Fertiletten (Chassot); Gestafortin (Merck KGaA); Lormin (Lilly); Luteran (Cassenne); Matrol; Normenon (Syntex); Menstridyl; Prostal (Teikoku Zoki); Traslan (Gramon).
C23H29ClO4; mol wt 404.93.
C 68.22%, H 7.22%, Cl 8.76%, O 15.80%.

Description and references

Orally active progestogen with antiandrogenic activity; has been used in combinations as an oral contraceptive. Prepn: Brückner, DE 1075114 (1960 to E. Merck, AG); Brückner et al., Ber. 94, 1225 (1961); Sciaky, Gazz. Chim. Ital. 91, 545 (1961); GB 932153; H. J. Ringold, A. Bowers, US 3485852 (1963, 1969 both to Syntex). Endocrinological activities: D. M. Brennan, R. J. Kraay, Acta Endocrinol. 44, 367 (1963). Metabolism: S. Honma et al., Chem. Pharm. Bull. 25, 2019 (1977). Clinical evaluation in prostatic carcinoma: R. Nishimura, K. Shida, Prostate, Suppl. 1, 27 (1981); in benign prostatic hypertrophy: T. Usui et al., Acta Urol. Jpn. 27, 327 (1981), B.A. 73, 27225 (1982). Review of carcinogenicity studies: IARC Monographs 21, 365-375 (1979).

Chemical structure

Properties

Crystals from methanol or ether, mp 212-214°. [α]D +6° (c = 1 in CHCl3). uv max: 283.5, 286 nm (ε 23400, 22100).

Derivative

Mixture with ethinyl estradiol.

Nomenclature

CAS number: 37301-55-6
Amenyl; Lutestral (Cassenne); Menova (Merck KGaA).

Derivative

Mixture with mestranol.

Nomenclature

CAS number: 8065-91-6
C-Quens; Gestamestrol (Hermal); Sequens.

Therapeutic Category

Progestogen; antineoplastic (hormonal).

Therapeutic Category (Veterinary)

Progestogen; estrus regulator.

Keywords

Antineoplastic (Hormonal); Progestogens; Progestogen