6694. Norelgestromin

Nomenclature

CAS number: 53016-31-2
(17α)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one oxime; 17-deacetylnorgestimate; 18-methylnorethindrone oxime; levonorgestrel 3-oxime; RWJ-10553.
C21H29NO2; mol wt 327.46.
C 77.02%, H 8.93%, N 4.28%, O 9.77%.

Description and references

Bioactive metabolite of norgestimate, q.v. Prepd as intermediate of norgestrel, q.v.: NL 7306609 (1973 to Richter Gedeon). Prepn and identification as norgestimate metabolite: S. F. Sisenwine et al., Contraception 15, 25 (1977). Pharmacology: J. L. McGuire et al., Am. J. Obstet. Gynecol. 163, 2127 (1990). Use as contraceptive patch: J. Jona et al., WO 9640355; eidem, US 5876746 (1996, 1999 both to Cygnus). Clinical pharmacokinetics: L. S. Abrams et al., Br. J. Clin. Pharmacol. 53, 141 (2002). Review of clinical pharmacology and efficacy: R. T. Burkman, Int. J. Fertil. 47, 69-76 (2002); B. L. Sicat, Pharmacotherapy 23, 472-480 (2003).

Chemical structure

Properties

Crystals, mp 112°.

Derivative

Combination with ethinyl estradiol.

Nomenclature

CAS number: 396715-57-4
Evra (Janssen-Cilag); Ortho Evra (Ortho).

Therapeutic Category

Progestogen; in combination with estrogen as transdermal contraceptive.

Keywords

Progestogen; Contraceptive (Transdermal)