Clogestone acetate

Clogestone acetate (USAN) (developmental code name AY-11440), also known as chlormadinol acetate or as 3β,17α-diacetoxy-6-chloropregna-4,6-diene-20-one,[1] is a steroidal progestin which was investigated as a progestin-only contraceptive and postcoital contraceptive but was never marketed.[2][3][4][5] It is the diacetate ester of clogestone, which, similarly was never marketed.[2] Clogestone acetate produces chlormadinone acetate as an active metabolite.[6][7]

Clogestone acetate

Clinical data
Other names	Chlormadinol acetate; AY-11440; 3β,17α-Diacetoxy-6-chloropregna-4,6-diene-20-one
Drug class	Progestogen; Progestogen ester
Identifiers
IUPAC name (1S,2R,5S,10R,11S,14R,15S)-14-acetyl-5-(acetyloxy)-8-chloro-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl acetate
CAS Number	3044-32-4
PubChem CID	20055455
ChemSpider	16736894
UNII	6RU186S3NO
KEGG	D03549
ChEMBL	ChEMBL2106484
CompTox Dashboard (EPA)	DTXSID70184523
Chemical and physical data
Formula	C25H33ClO5
Molar mass	448.98 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(CCC34C)OC(=O)C)Cl)C)OC(=O)C
InChI InChI=1S/C25H33ClO5/c1-14(27)25(31-16(3)29)11-8-20-18-13-22(26)21-12-17(30-15(2)28)6-9-23(21,4)19(18)7-10-24(20,25)5/h12-13,17-20H,6-11H2,1-5H3/t17-,18+,19-,20-,23+,24-,25-/m0/s1 Key:KSCZWFXQKITHSL-OKCNGXCSSA-N

See also

• List of progestogens
• List of progestogen esters

References

1. Gerald Litwack (2 December 2012). Biochemical Actions of Hormones. Elsevier. pp. 323–. ISBN 978-0-323-15189-4.
2. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 297–. ISBN 978-1-4757-2085-3.
3. D F Hawkins; M G Elder (22 October 2013). Human Fertility Control: Theory and Practice. Elsevier Science. pp. 3–. ISBN 978-1-4831-6361-1.
4. JUCKER (8 March 2013). Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des rechersches pharmaceutiques. Birkhäuser. pp. 321–. ISBN 978-3-0348-7098-6.
5. Hinselmann M, Jürgensen O, Hasselblatt I, Otten U, Prinz W, Taubert HD (1970). "[Clogestone acetate, a new orally effective progestagen]". Arch Gynakol (in German). 209 (2): 136–48. PMID 5537778.
6. Stern, Michael D.; Givner, Morris L. (1975). "MEASUREMENT OF SERUM CLOGESTONE ACETATE (AY-11, 440) BY A RADIORECEPTOR ASSAY: PRACTICAL APPROACH TO THE QUANTITATIVE DETERMINATION OF SYNTHETIC PROGESTINS". The Journal of Clinical Endocrinology & Metabolism. 40 (4): 728–731. doi:10.1210/jcem-40-4-728. ISSN 0021-972X.
7. Nuclear Science Abstracts. Oak Ridge Directed Operations, Technical Information Division. July 1975. p. 127.