Structural Formula Vector Image
Title: Norethindrone
CAS Registry Number: 68-22-4
CAS Name: (17a)-17-Hydroxy-19-norpregn-4-en-20-yn-3-one
Additional Names: 19-nor-17a-ethynyltestosterone; 17a-ethynyl-19-nortestosterone; 19-nor-17a-ethynyl-17b-hydroxy-4-androsten-3-one; 19-nor-17a-ethynylandrosten-17b-ol-3-one; anhydrohydroxynorprogesterone; 19-norethisterone; norpregneninolone; "mini-pill"
Trademarks: Camila (Barr); Conludag (Searle); Menzol (Schwarz); Micronor (Ortho); Micronovum (Janssen-Cilag); Mini-Pe (Searle); Norcolut (Gedeon Richter); Noriday (Searle); Primolut N (Schering AG); Utovlan (Searle)
Molecular Formula: C20H26O2
Molecular Weight: 298.42
Percent Composition: C 80.50%, H 8.78%, O 10.72%
Literature References: Prepn from 19-nor-4-androstene-3,17-dione: Djerassi et al., J. Am. Chem. Soc. 76, 4092 (1954); US 2744122 (1956 to Syntex); De Ruggieri, US 2849462 (1958). Pharmacokinetics: H. Singh et al., Am. J. Obstet. Gynecol. 135, 409 (1979); M. Humpel, Contraception 26, 83 (1982). Double-blind, comparative clinical trial: S. Koetsawang et al., ibid. 25, 231 (1982); A. Sheth et al., ibid. 243. Multicenter trial of combination with ethinyl estradiol: M. Toews et al., Curr. Ther. Res. 41, 509 (1987). Review of carcinogenicity studies: IARC Monographs 21, 441-460 (1979). Comprehensive description: A. P. Schroff, E. S. Moyer, Anal. Profiles Drug Subs. 4, 268-293 (1975).
Properties: Crystals from ethyl acetate, mp 203-204°. [a]D20 -31.7° (chloroform). First reported as [a]D20 -25° (chloroform). uv max (ethanol): 240 nm (log e 4.24).
Melting point: mp 203-204°
Optical Rotation: [a]D20 -31.7° (chloroform); [a]D20 -25° (chloroform)
Absorption maximum: uv max (ethanol): 240 nm (log e 4.24)
Derivative Type: Mixture with ethinyl estradiol
Trademarks: Binovum (Ortho-Cilag); Brevicon (Watson); Estrostep (Warner-Lambert); Modicon (Ortho); Neocon 1/35 (Ortho-Cilag); Norimin (Searle); Norinyl 1+35 (Watson); Ortho-Novum (Ortho); Ovcon (Warner-Chilcott); Ovysmen (Janssen-Cilag); Tri-Norinyl (Watson); Trinovum (Janssen-Cilag)
Derivative Type: Mixture with mestranol
Trademarks: Norinyl-1+50 (Watson); Ortho-Novin 1/50 (Ortho-Cilag); Ortho-Novum 1/50 (Ortho)
Derivative Type: Acetate
CAS Registry Number: 51-98-9
Trademarks: Aygestin (Barr); Milligynon (Schering AG); Norlutate (Warner-Lambert); Primolut-Nor (Schering AG)
Molecular Formula: C22H28O3
Molecular Weight: 340.46
Percent Composition: C 77.61%, H 8.29%, O 14.10%
Literature References: Prepn: O. Engelfried et al., US 2964537 (1960 to Schering AG).
Properties: Crystals from methylene chloride + hexane, mp 161-162°. uv max: 240 nm (e 18690).
Melting point: mp 161-162°
Absorption maximum: uv max: 240 nm (e 18690)
Derivative Type: Acetate, mixture with ethinyl estradiol
Trademarks: Etalontin (Parke-Davis); Primosiston (Schering AG); Anovlar (Schering AG); Gynovlar (Schering AG); Loestrin (Warner-Lambert); Minovlar (Schering AG); Norlestrin (Warner-Lambert)
Derivative Type: Enanthate
Trademarks: Noristerat (Schering AG)
Molecular Formula: C27H38O3
Molecular Weight: 410.59
Percent Composition: C 78.98%, H 9.33%, O 11.69%
Literature References: Clinical trial as injectable contraceptive: S. K. Banerjee et al., Contraception 30, 561 (1984).
CAUTION: Norethindrone is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-208.
Therap-Cat: Progestogen. Norethindrone and acetate in combination with estrogen as contraceptive (oral). Enanthate as contraceptive (injectable).
Keywords: Contraceptive (Injectable); Contraceptive (Oral); Progestogen.

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