3538. Elcometrine

Nomenclature

CAS number: 7759-35-5
17-(Acetyloxy)-16-methylene-19-norpregn-4-ene-3,20-dione; 16-methylene-17α-hydroxy-19-nor-4-pregnene-3,20-dione 17-acetate; 16-methylene-17α-acetoxy-19-norpregn-4-ene-3,20-dione; ST-1435; Nestorone (Pop. Council).
C23H30O4; mol wt 370.48.
C 74.56%, H 8.16%, O 17.27%.

Description and references

Synthetic, non-orally active progestin. Prepn: V. Schwarz et al., Tetrahedron Lett. 1967, 1925; eidem, Collect. Czech. Chem. Commun. 33, 4337 (1968). Pharmacology: N. Kumar et al., Steroids 65, 629 (2000). Clinical pharmacokinetics: G. Noé et al., Contraception 48, 548 (1993). Metabolism: O. Heikinheimo et al., ibid. 50, 275 (1994). Clinical trial of subdermal implant: S. Diaz et al., ibid. 51, 33 (1995). Clinical trial of vaginal rings delivery system: I. Sivin et al., ibid. 69, 137 (2004); idem et al., ibid. 71, 122 (2005).

Chemical structure

Properties

Crystals from methanol, mp 178-179°. [α]D21 -105° (c = 1.2 in chloroform). uv max (methanol): 240 nm (log ε 4.21).

Therapeutic Category

Progestogen; contraceptive (implantable).

Keywords

Progestogen; Contraceptive (Implantable)