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Oxogestone phenpropionate

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Oxogestone phenpropionate
Clinical data
Other namesOxogesterone 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
Routes of
administration		intramuscular injection
Drug classProgestogen; Progestogen ester
Identifiers
  • [(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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC29H38O3
Molar mass434.610 g/mol g·mol−1
3D model (JSmol)
  • CC(C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)OC(=O)CCC5=CC=CC=C5
  • InChI=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
  • Key:LHPBUFXEIOLURH-GQZONRFDSA-N

Oxogestone phenpropionate (OPP'; USANTooltip 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.[1][2][3][4][5][6][7] 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.[5] OPP is the 20β-(3-phenylpropionate) ester of oxogestone, which, similarly, was never marketed.[1]

See also

References

  1. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 919–. ISBN 978-1-4757-2085-3.
  2. ^ George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1577–. ISBN 978-1-351-78989-9.
  3. ^ van der Vies, J. (1970). "Model studies in vitro with long-acting hormonal preparations". Acta Endocrinologica. 64 (4): 656–669. doi:10.1530/acta.0.0640656. ISSN 0804-4643. PMID 5468664.
  4. ^ 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
  5. ^ a b Toppozada M (June 1977). "The clinical use of monthly injectable contraceptive preparations". Obstet Gynecol Surv. 32 (6): 335–47. doi:10.1097/00006254-197706000-00001. PMID 865726.
  6. ^ Petrow V (1970). "The contraceptive progestagens". Chem. Rev. 70 (6): 713–26. doi:10.1021/cr60268a004. PMID 4098492.
  7. ^ Goldsmith, A., & Toppozada, M. (1983). Long-acting contraception. pp. 94-95 https://www.popline.org/node/423289


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