3454. Drospirenone

Nomenclature

CAS number: 67392-87-4
(2′S,6R,7R,8R,9S,10R,13S,14S,15S,16S)-1,3′,4′,6,7,8,9,10,11,12,13,14,15,16,20,21-Hexadecahydro-10,13-dimethylspiro[17H-dicyclopropa[6,7:15,16]cyclopenta[a]phenanthrene-17,2′(5′H)-furan]-3,5′(2H)-dione; 6β,7β,15β,16β-dimethylene-3-oxo-4-androstene-[17(β-1′)-spiro-5′]perhydrofuran-2′-one; 6β,7β,15β,16β-dimethylen-3-oxo-17α-pregn-4-ene-21,17-carbolactone; dihydrospirorenone; ZK-30595.
C24H30O3; mol wt 366.49.
C 78.65%, H 8.25%, O 13.10%.

Description and references

Synthetic progestogen exhibiting antimineralocorticoid and antiandrogenic activity. Prepn: R. Wiechert et al., DE 2652761; eidem, US 4129564 (both 1978 to Schering AG); D. Bittler et al., Angew. Chem. 94, 718 (1982). HPLC determn in human plasma: W. Krause, U. Jakobs, J. Chromatogr. 230, 37 (1982). Pharmacological profile: P. Muhn et al., Contraception 51, 99 (1995). Review of synthesis: H. Laurent et al., J. Steroid Biochem. 19, 771-776 (1983); of pharmacology and clinical experience: W. Oelkers, Mol. Cell. Endocrinol. 217, 255-261 (2004).

Chemical structure

Properties

mp 201.3°. [α]D22 -182° (c = 0.5 in chloroform). uv (methanol): 265 nm (ε 19000).

Derivative

Mixture with ethinyl estradiol.

Nomenclature

Angeliq (Schering AG); Yasmin (Schering AG); Yaz (Berlex).

Description and references

Clinical trial as oral contraceptive: K. S. Parsey, A. Pong, Contraception 61, 105 (2000); in treatment of menopausal symptoms: R. Schürmann et al., Climacteric 7, 189 (2004).

Therapeutic Category

Progestogen. In combination with estrogen as oral contaceptive and in treatment of menopausal symptoms.

Keywords

Progestogen; Contraceptive (Oral)