Oxogestone phenpropionate

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Oxogestone phenpropionate
Oxogestone phenpropionate.svg
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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC29H38O3
Molar mass434.610 g/mol g·mol−1
3D model (JSmol)

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

Progestogen Form Major brand names Class TFD
(14 days)
POIC-D
(2–3 months)
CIC-D
(month)
Duration
Algestone acetophenide Oil solution Perlutal, Topasel, Yectames Pregnane ? 75–150 mg 100 mg ≈ 14–32 days
Cyproterone acetate Oil solution Androcur Depot Pregnane ? 300 mg ≈ 20 days
Dydrogesteronea Aqueous suspension Retropregnane ? 100 mg ≈ 16–38 days
Gestonorone caproate Oil solution Depostat, Primostat Norpregnane 50 mg 25–50 mg ≈ 8–13 days
Hydroxyprogesterone acetatea Aqueous suspension Pregnane 350 mg 150–350 mg ≈ 9–16 days
Hydroxyprogesterone caproate Oil solution Delalutin, Proluton, Makena Pregnane 250–500 mgb 250–500 mg 65–500 mg ≈ 5–21 days
Levonorgestrel butanoatea Aqueous suspension Gonane ? 5–50 mg ≈ 3–6 months
Lynestrenol phenylpropionatea Oil solution Estrane ? 50–100 mg ≈ 14–30 days
Medroxyprogesterone acetate Aqueous suspension Depo-Provera Pregnane 50–100 mg 150 mg 25 mg 50–150 mg ≈ 14–50+ days
Megestrol acetate Aqueous suspension Mego-E Pregnane ? 25 mg 25 mg ≈ >14 daysc
Norethisterone enanthate Oil solution Noristerat, Mesigyna Estrane 100–200 mg 200 mg 50 mg 50–200 mg ≈ 11–52 days
Oxogestone phenylpropionatea Oil solution Norpregnane ? 100 mg ≈ 19–20 days
Progesterone Oil solution Progestaject, Gestone, Strone Pregnane 200 mgb 25–350 mg ≈ 2–6 days
Aqueous suspension Agolutin Depot Pregnane 50–200 mg 50–300 mg ≈ 7–14 days
Note: All by intramuscular or subcutaneous injection. All are synthetic except for P4, which is bioidentical. P4 production during the luteal phase is ~25 (15–50) mg/day. The OID of OHPC is 250 to 500 mg/month. Footnotes: a = Never marketed by this route. b = In divided doses (2 × 125 or 250 mg for OHPC, 10 × 20 mg for P4). c = Half-life is ~14 days. Sources: Main: See template.

See also[edit]

References[edit]

  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