Oxogestone phenpropionate

Oxogestone phenpropionate (OPP; USAN) (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]

Parenteral potencies and durations of progestogens[lower-alpha 1][lower-alpha 2]
Compound Form Dose for specific uses (mg)[lower-alpha 3] DOA[lower-alpha 4]
TFD[lower-alpha 5] POICD[lower-alpha 6] CICD[lower-alpha 7]
Algestone acetophenideOil soln.-–75–15014–32 d
Gestonorone caproateOil soln.25–50––8–13 d
Hydroxyprogest. acetate[lower-alpha 8]Aq. susp.350––9–16 d
Hydroxyprogest. caproateOil soln.250–500[lower-alpha 9]–250–5005–21 d
Medroxyprog. acetateAq. susp.50–1001502514–50+ d
Megestrol acetateAq. susp.-–25>14 d
Norethisterone enanthateOil soln.100–2002005011–52 d
ProgesteroneOil soln.200[lower-alpha 9]––2–6 d
Aq. soln. ?––1–2 d
Aq. susp.50–200––7–14 d
Notes and sources:
  1. Sources: [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27]
  2. All given by intramuscular or subcutaneous injection.
  3. Progesterone production during the luteal phase is ~25 (15–50) mg/day. The OID of OHPC is 250 to 500 mg/month.
  4. Duration of action in days.
  5. Usually given for 14 days.
  6. Usually dosed every two to three months.
  7. Usually dosed once monthly.
  8. Never marketed or approved by this route.
  9. In divided doses (2 × 125 or 250 mg for OHPC, 10 × 20 mg for P4).
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
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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC29H38O3
Molar mass434.620 g·mol−1
3D model (JSmol)
SMILES
  • CC(C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)OC(=O)CCC5=CC=CC=C5
InChI
  • 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

See also

References
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  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. 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.
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  8. Knörr K, Beller FK, Lauritzen C (17 April 2013). Lehrbuch der Gynäkologie. Springer-Verlag. pp. 214–. ISBN 978-3-662-00942-0.
  9. Knörr K, Knörr-Gärtner H, Beller FK, Lauritzen C (8 March 2013). Geburtshilfe und Gynäkologie: Physiologie und Pathologie der Reproduktion. Springer-Verlag. pp. 583–. ISBN 978-3-642-95583-9.
  10. A. Labhart (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 554–. ISBN 978-3-642-96158-8.
  11. Horský J, Presl J (1981). "Hormonal Treatment of Disorders of the Menstrual Cycle". In Horsky J, Presl K (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 309–332. doi:10.1007/978-94-009-8195-9_11. ISBN 978-94-009-8195-9.
  12. Joachim Ufer (1969). The Principles and Practice of Hormone Therapy in Gynaecology and Obstetrics. de Gruyter. p. 49. 17α-Hydroxyprogesterone caproate is a depot progestogen which is entirely free of side actions. The dose required to induce secretory changes in primed endometrium is about 250 mg. per menstrual cycle.
  13. Willibald Pschyrembel (1968). Praktische Gynäkologie: für Studierende und Ärzte. Walter de Gruyter. pp. 598, 601. ISBN 978-3-11-150424-7.
  14. Ferin J (September 1972). "Effects, Duration of Action and Metabolism in Man". In Tausk M (ed.). Pharmacology of the Endocrine System and Related Drugs: Progesterone, Progestational Drugs and Antifertility Agents. Vol. II. Pergamon Press. pp. 13–24. ISBN 978-0080168128. OCLC 278011135.
  15. Henzl MR, Edwards JA (10 November 1999). "Pharmacology of Progestins: 17α-Hydroxyprogesterone Derivatives and Progestins of the First and Second Generation". In Sitruk-Ware R, Mishell DR (eds.). Progestins and Antiprogestins in Clinical Practice. Taylor & Francis. pp. 101–132. ISBN 978-0-8247-8291-7.
  16. Janet Brotherton (1976). Sex Hormone Pharmacology. Academic Press. p. 114. ISBN 978-0-12-137250-7.
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  22. Moltz L, Haase F, Schwartz U, Hammerstein J (May 1983). "[Treatment of virilized women with intramuscular administration of cyproterone acetate]" [Efficacy of Intra muscularly Applied Cyproterone Acetate in Hyperandrogenism]. Geburtshilfe Und Frauenheilkunde. 43 (5): 281–7. doi:10.1055/s-2008-1036893. PMID 6223851.
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