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Chemical compound
Clogestone acetate Other names Chlormadinol acetate; AY-11440; 3β,17α-Diacetoxy-6-chloropregna-4,6-diene-20-one Drug class Progestogen ; Progestogen ester
(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 PubChem CID ChemSpider UNII KEGG ChEMBL CompTox Dashboard (EPA ) Formula C 25 H 33 Cl O 5 Molar mass 448.98 g·mol−1 3D model (JSmol )
CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(CCC34C)OC(=O)C)Cl)C)OC(=O)C
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
Clogestone acetate (USAN Tooltip United States Adopted Name ) (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]
^ Litwack G (2 December 2012). Biochemical Actions of Hormones . Elsevier. pp. 323–. ISBN 978-0-323-15189-4 .
^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 297–. ISBN 978-1-4757-2085-3 .
^ Hawkins DR, Elder MG (22 October 2013). Human Fertility Control: Theory and Practice . Elsevier Science. pp. 3–. ISBN 978-1-4831-6361-1 .
^ Harper MJ (8 March 2013). "Contraception — retrospect and prospect" . Progress in Drug Research, vol. 21 . Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des rechersches pharmaceutiques. Vol. 21. Birkhäuser. pp. 293–407. doi :10.1007/978-3-0348-7098-6_4 . ISBN 978-3-0348-7098-6 . PMID 339271 .
^ Hinselmann M, Jürgensen O, Hasselblatt I, Otten U, Prinz W, Taubert HD (August 1970). "[Clogestone acetate, a new orally effective progestagen]". Archiv Fur Gynakologie (in German). 209 (2): 136–148. doi :10.1007/BF00668180 . PMID 5537778 .
^ Stern MD, Givner ML (April 1975). "Measurement of serum clogestone acetate (AY-11,440) by a radioreceptor assay: a practical approach to the quantitative determination of synthetic progestins". The Journal of Clinical Endocrinology and Metabolism . 40 (4): 728–731. doi :10.1210/jcem-40-4-728 . PMID 1127082 .
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g., levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g., norethisterone acetate , norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g., nandrolone decanoate , nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g., trenbolone acetate , trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (PAQR Tooltip Progestin and adipoQ receptor )