oxogestone phenpropionate

{{short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = [(1R)-1-[(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl] 3-phenylpropanoate

| image = Oxogestone phenpropionate.svg

| width = 250px

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| routes_of_administration = intramuscular injection

| class = Progestogen; Progestogen ester

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| CAS_number_Ref =

| CAS_number = 16915-80-3

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| PubChem = 20055360

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| ChemSpiderID = 16736681

| UNII = 7IA4J676HM

| ChEMBL = 2107303

| KEGG = D05308

| synonyms = Oxogesterone phenpropionate; Xinogestone; Oxageston; 20β-Hydroxy-19-norprogesterone phenylpropionate; 20β-Dihydro-19-norprogesterone 20β-(3-phenylpropionate); 20β-Hydroxy-19-norpregn-4-en-3-one 20β-(3-phenylpropionate); (20R)-3-Oxo-19-norpregn-4-en-20-yl 3-phenylpropanoate

| C=29 | H=38 | O=3

| SMILES = CC(C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)OC(=O)CCC5=CC=CC=C5

| StdInChI_Ref =

| StdInChI = 1S/C29H38O3/c1-19(32-28(31)15-8-20-6-4-3-5-7-20)26-13-14-27-25-11-9-21-18-22(30)10-12-23(21)24(25)16-17-29(26,27)2/h3-7,18-19,23-27H,8-17H2,1-2H3/t19-,23+,24-,25-,26-,27+,29-/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = LHPBUFXEIOLURH-GQZONRFDSA-N

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Oxogestone phenpropionate (OPP; {{abbrlink|USAN|United States Adopted Name}}) (former developmental code name or tentative brand name Oxageston), also known as xinogestone, as well as 20β-hydroxy-19-norprogesterone 20β-(3-phenylpropionate), is a progestin related to the 19-norprogesterone derivatives which was developed as an injectable hormonal contraceptive, specifically a progestogen-only injectable contraceptive, in the 1960s and early 1970s but was never marketed.{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA919|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=919–}}{{cite book|author=George W.A Milne|title=Drugs: Synonyms and Properties: Synonyms and Properties|url=https://books.google.com/books?id=xUlaDwAAQBAJ&pg=PT1577|date=8 May 2018|publisher=Taylor & Francis|isbn=978-1-351-78989-9|pages=1577–}}{{cite journal|last1=van der Vies|first1=J.|title=Model studies in vitro with long-acting hormonal preparations|journal=Acta Endocrinologica|volume=64|issue=4|year=1970|pages=656–669|issn=0804-4643|doi=10.1530/acta.0.0640656|pmid=5468664}}Heeres, S. G. (1967). Preliminary results with a long-acting progestational preparation. In: Wood, C. and Walters, W.A., eds. Fifth World Congress of Gynaecology and Obstetrics, Sydney, September 1967. New York Appleton-Century-Crofts, 1967. p. 348 http://www.popline.org/node/475027{{cite journal | vauthors = Toppozada M | title = The clinical use of monthly injectable contraceptive preparations | journal = Obstet Gynecol Surv | volume = 32 | issue = 6 | pages = 335–47 | date = June 1977 | pmid = 865726 | doi = 10.1097/00006254-197706000-00001 }}{{cite journal | vauthors = Petrow V | title = The contraceptive progestagens | journal = Chem. Rev. | volume = 70 | issue = 6 | pages = 713–26 | year = 1970 | pmid = 4098492 | doi = 10.1021/cr60268a004}}{{cite book | author = Mokhtar K. Toppozada | chapter = Monthly Injectable Contraceptives | pages = 93–103 | editor1 = Alfredo Goldsmith | editor2 = Mokhtar Toppozada | title = Long-Acting Contraception | year = 1983 | oclc = 35018604 | url = https://scholar.google.com/scholar?cluster=14664537528797672080}} It was studied at a dose of 50 to 75 mg once a month by intramuscular injection but was associated with a high failure rate with this regimen and was not further developed. OPP is the 20β-(3-phenylpropionate) ester of oxogestone, which, similarly, was never marketed.

{{Parenteral potencies and durations of progestogens}}