Gestrinone
Title: Gestrinone
CAS Registry Number: 16320-04-0
CAS Name: (17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one
Additional Names: 13b-ethyl-17a-ethynyl-17b-hydroxy-4,9,11-gonatrien-3-one; 13b-ethyl-17a-ethynyl-D4,9,11-gonatriene-17b-ol-3-one; ethylnorgestrienone
Manufacturers' Codes: A-46745; R-2323; RU-2323
Trademarks: Dimetriose (HMR); Dimetrose (Poli); Nemestran (HMR); Tridomose (HMR)
Molecular Formula: C21H24O2
Molecular Weight: 308.41
Percent Composition: C 81.78%, H 7.84%, O 10.38%
Literature References: Steroidal antiestrogen, antiprogestogen, analog of norgestrienone, q.v. Prepn: G. Nomine et al., US 3257278; NL 6607609 C.A. 67, 44029d (1967); D. Bertin, A. Pierdet, US 3478067 (1966, 1966, 1969 all to Roussel-UCLAF). Radioimmunoassay in human plasma: J. Frick et al., Urol. Res. 5, 55 (1977). HPLC-MS-MS determn in plasma: Q. Wang et al., J. Chromatogr. B 746, 151 (2000). Clinical evaluation of contraceptive efficacy: G. Azadian-Boulanger et al., Am. J. Obstet. Gynecol. 125, 1049 (1976); of use in fibrocystic breast disease: E. M. Coutinho, G. Azadian-Boulanger, Int. J. Gynaecol. Obstet. 22, 363 (1984); in endometriosis: E. J. Thomas, I. D. Cooke, Br. Med. J. 294, 272 (1987); E. M. Coutinho, G. Azadian-Boulanger, Fertil. Steril. 49, 418 (1988).
Properties: Crystals from ethyl acetate and benzene-cyclohexane (1:1), mp 154°. [a]D20 +84.6° (c = 0.41 in methanol).
Melting point: mp 154°
Optical Rotation: [a]D20 +84.6° (c = 0.41 in methanol)
Therap-Cat: Antigonadotropin.
Keywords: Antigonadotropin.

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