6704. Norgestrel

Nomenclature

CAS number: 6533-00-2
(17α)-(±)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one; Wy-3707; Neogest (Schering AG); Ovrette (Wyeth).
C21H28O2; mol wt 312.45.
C 80.72%, H 9.03%, O 10.24%.

Description and 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).

Chemical structure

Properties

Crystals from methanol, mp 205-207°. uv max (ethanol): 241 nm (ε 16700).

Derivative

Mixture with ethinyl estradiol.

Nomenclature

CAS number: 8056-51-7
Lo/Ovral (Wyeth); Ovral (Wyeth); Stédiril (Wyeth).

Description and references

Clinical efficiacy as oral contraceptive: T. R. Dunson et al., Contraception 48, 109 (1993)

Derivative

(+)-Form.

Nomenclature

CAS number: 797-64-8
(8α,9β,10α,13α,14β)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one; dextronorgestrel.

Description and references

Crystal structure determn: N. J. DeAngelis et al., Acta Crystallogr. 31B, 2040 (1975).

Properties

Crystals, mp 238-242°. [α]D25 +40.7° (CHCl3).

Derivative

(-)-Form.

Nomenclature

CAS number: 797-63-7
17-Ethynyl-18-methyl-19-nortestosterone; 13β-ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-one; levonorgestrel; d-norgestrel; dexnorgestrel (obsolete); Levonelle (Schering AG); Levonova (Schering AG); Microlut (Schering AG); Microval (Wyeth); Mirena (Schering AG); Norgeston (Schering AG); Norlevo (HRA Pharma); Norplant (Wyeth).

Description and 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"ahteenm"aki et al., Steroids 65, 693-697 (2000); T. Luukkainen, ibid. 699-702.

Properties

Crystals from methanol, mp 235-237°. [α]D20 -32.4° (c = 0.496 in CHCl3). uv max (methanol): 241 nm (ε 16770).

Derivative

Mixture of levonorgestrel with ethinyl estradiol.

Nomenclature

CAS number: 39366-37-5
Levlen (Berlex); Logynon (Schering AG); Microgynon (Schering AG); Nordette (Wyeth); Ovran (Wyeth); Ovranette (Wyeth); Tetragynon (Schering AG); Tri-Levlen (Berlex); Trinordiol (Wyeth); Triphasil (Wyeth).

Description and references

Clinical trial in acne treatment: L. J. Diaz-Sandoval et al., Fertil. Steril. 76, 461 (2001).

Therapeutic Category

Progestogen; oral contraceptive; as contraceptive implant.

Keywords

Contraceptive (Oral); Progestogen

Levonorgestrel: Contraceptive (Implantable)