clogestone acetate

{{Short description|Chemical compound}}

{{Infobox drug

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| IUPAC_name = (1S,2R,5S,10R,11S,14R,15S)-14-acetyl-5-(acetyloxy)-8-chloro-2,15-dimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadeca-6,8-dien-14-yl acetate

| image = Clogestone acetate.svg

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| class = Progestogen; Progestogen ester

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| CAS_number = 3044-32-4

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| PubChem = 20055455

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| ChemSpiderID = 16736894

| UNII = 6RU186S3NO

| ChEMBL = 2106484

| KEGG = D03549

| synonyms = Chlormadinol acetate; AY-11440; 3β,17α-Diacetoxy-6-chloropregna-4,6-diene-20-one

| C=25 | H=33 | Cl=1 | O=5

| SMILES = CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(CCC34C)OC(=O)C)Cl)C)OC(=O)C

| StdInChI_Ref =

| StdInChI = 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

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| StdInChIKey = KSCZWFXQKITHSL-OKCNGXCSSA-N

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Clogestone acetate ({{abbrlink|USAN|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,{{cite book| vauthors = Litwack G |title=Biochemical Actions of Hormones|url=https://books.google.com/books?id=et3Lq-TitzAC&pg=PA323|date=2 December 2012|publisher=Elsevier|isbn=978-0-323-15189-4|pages=323–}} is a steroidal progestin which was investigated as a progestin-only contraceptive and postcoital contraceptive but was never marketed.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA297|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=297–}}{{cite book| vauthors = Hawkins DR, Elder MG |title=Human Fertility Control: Theory and Practice|url=https://books.google.com/books?id=1lL0AgAAQBAJ&pg=PA3|date=22 October 2013|publisher=Elsevier Science|isbn=978-1-4831-6361-1|pages=3–}}{{cite book | vauthors = Harper MJ | chapter = Contraception — retrospect and prospect | title=Progress in Drug Research, vol. 21| series = Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des rechersches pharmaceutiques| volume = 21 | pages = 293–407 | date = 8 March 2013 | pmid = 339271 | chapter-url = https://books.google.com/books?id=VFb2BwAAQBAJ&pg=PA321 | publisher = Birkhäuser | doi = 10.1007/978-3-0348-7098-6_4 | isbn = 978-3-0348-7098-6 }}{{cite journal | vauthors = Hinselmann M, Jürgensen O, Hasselblatt I, Otten U, Prinz W, Taubert HD | title = [Clogestone acetate, a new orally effective progestagen] | language = de | journal = Archiv für Gynäkologie | volume = 209 | issue = 2 | pages = 136–148 | date = August 1970 | pmid = 5537778 | doi = 10.1007/BF00668180 }} It is the diacetate ester of clogestone, which, similarly was never marketed. Clogestone acetate produces chlormadinone acetate as an active metabolite.{{cite journal | vauthors = Stern MD, Givner ML | title = Measurement of serum clogestone acetate (AY-11,440) by a radioreceptor assay: a practical approach to the quantitative determination of synthetic progestins | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 40 | issue = 4 | pages = 728–731 | date = April 1975 | pmid = 1127082 | doi = 10.1210/jcem-40-4-728 }}