Medroxyprogesterone
Title: Medroxyprogesterone
CAS Registry Number: 520-85-4
CAS Name: (6a)-17-Hydroxy-6-methylpregn-4-ene-3,20-dione
Additional Names: 17a-hydroxy-6a-methylprogesterone; 6a-methyl-17a-hydroxyprogesterone; 6a-methyl-4-pregnen-17a-ol-3,20-dione
Molecular Formula: C22H32O3
Molecular Weight: 344.49
Percent Composition: C 76.70%, H 9.36%, O 13.93%
Literature 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).
Properties: Crystals from chloroform, mp 220-223.5°. [a]D25 +75° (in chloroform). uv max (ethanol): 241 nm (e 16000).
Melting point: mp 220-223.5°
Optical Rotation: [a]D25 +75° (in chloroform)
Absorption maximum: uv max (ethanol): 241 nm (e 16000)
 
Derivative Type: 17-Acetate
CAS Registry Number: 71-58-9
Additional Names: 17a-Acetoxy-6a-methylprogesterone; 6-a-methyl-17a-acetoxyprogesterone; MAP
Trademarks: 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)
Molecular Formula: C24H34O4
Molecular Weight: 386.52
Percent Composition: C 74.58%, H 8.87%, O 16.56%
Properties: Crystals from methanol, mp 207-209°. [a]D +61° (in chloroform). uv max (ethanol): 240 nm (e 15900). Freely sol in chloroform; sol in acetone, dioxane; sparingly sol in ethanol, methanol; slightly sol in ether. Insol in water.
Melting point: mp 207-209°
Optical Rotation: [a]D +61° (in chloroform)
Absorption maximum: uv max (ethanol): 240 nm (e 15900)
 
Therap-Cat: Progestogen; contraceptive (injectable); antineoplastic (hormonal).
Therap-Cat-Vet: Progestogen; estrus regulator.
Keywords: Antineoplastic (Hormonal); Progestogens; Contraceptive (Injectable); Progestogen.

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