6697. Norethindrone

Nomenclature

CAS number: 68-22-4
(17α)-17-Hydroxy-19-norpregn-4-en-20-yn-3-one; 19-nor-17α-ethynyltestosterone; 17α-ethynyl-19-nortestosterone; 19-nor-17α-ethynyl-17β-hydroxy-4-androsten-3-one; 19-nor-17α-ethynylandrosten-17β-ol-3-one; anhydrohydroxynorprogesterone; 19-norethisterone; norpregneninolone; “mini-pill”; 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).
C20H26O2; mol wt 298.42.
C 80.50%, H 8.78%, O 10.72%.

Description and 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).

Chemical structure

Properties

Crystals from ethyl acetate, mp 203-204°. [α]D20 -31.7° (chloroform). First reported as [α]D20 -25° (chloroform). uv max (ethanol): 240 nm (log ε 4.24).

Derivative

Mixture with ethinyl estradiol.

Nomenclature

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

Mixture with mestranol.

Nomenclature

Norinyl-1+50 (Watson); Ortho-Novin 1/50 (Ortho-Cilag); Ortho-Novum 1/50 (Ortho).

Derivative

Acetate.

Nomenclature

CAS number: 51-98-9
Aygestin (Barr); Milligynon (Schering AG); Norlutate (Warner-Lambert); Primolut-Nor (Schering AG).
C22H28O3; mol wt 340.46.
C 77.61%, H 8.29%, O 14.10%.

Description and 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 (ε 18690).

Derivative

Acetate, mixture with ethinyl estradiol.

Nomenclature

Etalontin (Parke-Davis); Primosiston (Schering AG); Anovlar (Schering AG); Gynovlar (Schering AG); Loestrin (Warner-Lambert); Minovlar (Schering AG); Norlestrin (Warner-Lambert).

Derivative

Enanthate.

Nomenclature

Noristerat (Schering AG).
C27H38O3; mol wt 410.59.
C 78.98%, H 9.33%, O 11.69%.

Description and 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.

Therapeutic Category

Progestogen. Norethindrone and acetate in combination with estrogen as contraceptive (oral). Enanthate as contraceptive (injectable).

Keywords

Contraceptive (Injectable); Contraceptive (Oral); Progestogen