Title: Norgestrel
CAS Registry Number: 6533-00-2
CAS Name: (17a)-(±)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
Manufacturers' Codes: Wy-3707
Trademarks: Neogest (Schering AG); Ovrette (Wyeth)
Molecular Formula: C21H28O2
Molecular Weight: 312.45
Percent Composition: C 80.72%, H 9.03%, O 10.24%
Literature References: The bioactive enantiomer is levorotatory. Prepn: H. Smith,
BE 623844 (1963),
C.A. 61, 4427c (1964); G. A. Hughes, H. Smith,
US 3959322 (1976 to Herchel Smith); H. Smith
et al., Experientia 19, 394 (1963);
eidem, J. Chem. Soc. 1964, 4472; M. Rosenberger
et al., Helv. Chim. Acta 54, 2857 (1971). Comprehensive description: A. M. Sopirak, L. F. Cullen,
Anal. Profiles Drug Subs. 4, 294-318 (1975).
Properties: Crystals from methanol, mp 205-207°. uv max (ethanol): 241 nm (e 16700).
Melting point: mp 205-207°
Absorption maximum: uv max (ethanol): 241 nm (e 16700)
Derivative Type: Mixture with ethinyl estradiol
CAS Registry Number: 8056-51-7
Trademarks: Lo/Ovral (Wyeth); Ovral (Wyeth); Stédiril (Wyeth)
Literature References: Clinical efficiacy as oral contraceptive: T. R. Dunson
et al., Contraception 48, 109 (1993)
Derivative Type: (+)-Form
CAS Registry Number: 797-64-8
Synonyms: (8a,9b,10a,13a,14b)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one; dextronorgestrel
Literature References: Crystal structure determn: N. J. DeAngelis
et al., Acta Crystallogr. 31B, 2040 (1975).
Properties: Crystals, mp 238-242°. [a]D25 +40.7° (CHCl3).
Melting point: mp 238-242°
Optical Rotation: [a]D25 +40.7° (CHCl3)
Derivative Type: (-)-Form
CAS Registry Number: 797-63-7
Synonyms: 17-Ethynyl-18-methyl-19-nortestosterone; 13b-ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-one; levonorgestrel; D-norgestrel; dexnorgestrel (obsolete)
Trademarks: Levonelle (Schering AG); Levonova (Schering AG); Microlut (Schering AG); Microval (Wyeth); Mirena (Schering AG); Norgeston (Schering AG); Norlevo (HRA Pharma); Norplant (Wyeth)
Literature References: Prepn: C. Rufer
et al., Ann. 702, 141 (1967); H. Baier
et al., Helv. Chim. Acta 68, 1054 (1985). Metabolism: F. Z. Stanczyk, S. Roy,
Contraception 42, 67 (1990). Comparative clinical trial with mifepristone,
q.v., in emergency contraception: H. von Hertzen
et al., Lancet 360, 1803 (2002). Review of clinical pharmacokinetics: K. Fotherby,
Clin. Pharmacokinet. 28, 203-215 (1995); of clinical efficacy of subdermal implant: A. J. Coukell, J. A. Balfour,
Drugs 55, 861-887 (1998); of intrauterine implant: P. L?hteenm?ki
et al., Steroids 65, 693-697 (2000); T. Luukkainen,
ibid. 699-702.
Properties: Crystals from methanol, mp 235-237°. [a]D20 -32.4° (c = 0.496 in CHCl3). uv max (methanol): 241 nm (e 16770).
Melting point: mp 235-237°
Optical Rotation: [a]D20 -32.4° (c = 0.496 in CHCl3)
Absorption maximum: uv max (methanol): 241 nm (e 16770)
Derivative Type: Mixture of levonorgestrel with ethinyl estradiol
CAS Registry Number: 39366-37-5
Trademarks: Levlen (Berlex); Logynon (Schering AG); Microgynon (Schering AG); Nordette (Wyeth); Ovran (Wyeth); Ovranette (Wyeth); Tetragynon (Schering AG); Tri-Levlen (Berlex); Trinordiol (Wyeth); Triphasil (Wyeth)
Literature References: Clinical trial in acne treatment: L. J. Diaz-Sandoval
et al., Fertil. Steril. 76, 461 (2001).
Therap-Cat: Progestogen; oral contraceptive; as contraceptive implant.
Keywords: Contraceptive (Oral); Progestogen.
