5793. Medroxyprogesterone

Nomenclature

CAS number: 520-85-4
(6α)-17-Hydroxy-6-methylpregn-4-ene-3,20-dione; 17α-hydroxy-6α-methylprogesterone; 6α-methyl-17α-hydroxyprogesterone; 6α-methyl-4-pregnen-17α-ol-3,20-dione.
C22H32O3; mol wt 344.49.
C 76.70%, H 9.36%, O 13.93%.

Description and references

Orally active progestogen; formerly used in combinations as oral contraceptive. Prepn: J. C. Babcock et al., J. Am. Chem. Soc. 80, 2904 (1958); GB 866381; G. B. Spero, US 3377364 (1961, 1968 both to Upjohn); P. Ruggieri, C. Ferrari, US 3043832 (1962 to Ormonoterapia Richter); B. Camerino et al., US 3061616 (1962 to Farmitalia). HPLC determn in plasma: J. Read, G. Mould, J. Chromatogr. 341, 437 (1985). Comparative clinical trial with norethisterone as injectable contraceptive: H. K. Toppozada et al., Contraception 28, 1 (1983). Clinical trial in advanced breast cancer: M. Izuo et al., Cancer 56, 2576 (1985). Review of pharmacology and clinical uses: I. S. Fraser, E. Weisberg, Med. J. Aust. 1, Suppl. 1, 3-19 (1981).

Chemical structure

Properties

Crystals from chloroform, mp 220-223.5°. [α]D25 +75° (in chloroform). uv max (ethanol): 241 nm (ε 16000).

Derivative

17-Acetate.

Nomenclature

CAS number: 71-58-9
17α-Acetoxy-6α-methylprogesterone; 6-α-methyl-17α-acetoxyprogesterone; MAP; Amen (Elan); Clinovir (Pharmacia); Cycrin (Wyeth); Depo-Clinovir (Pharmacia); Depo-Prodasone (Pfizer); Depo-Provera (Pharmacia & Upjohn); Farlutal (Pharmacia); Gestoral (Novartis); Hysron (Kyowa); Oragest (Pharmagyn); Perlutex (Leo Pharm); Provera (Pharmacia & Upjohn); Veramix (Pharmacia).
C24H34O4; mol wt 386.52.
C 74.58%, H 8.87%, O 16.56%.

Properties

Crystals from methanol, mp 207-209°. [α]D +61° (in chloroform). uv max (ethanol): 240 nm (ε 15900). Freely sol in chloroform; sol in acetone, dioxane; sparingly sol in ethanol, methanol; slightly sol in ether. Insol in water.

Therapeutic Category

Progestogen; contraceptive (injectable); antineoplastic (hormonal).

Therapeutic Category (Veterinary)

Progestogen; estrus regulator.

Keywords

Antineoplastic (Hormonal); Progestogens; Contraceptive (Injectable); Progestogen