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]
| 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. | ||||||||
 | |
| Clinical data | |
|---|---|
| Other names | 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 |
| Routes of administration | intramuscular injection |
| Drug class | Progestogen; Progestogen ester |
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| Formula | C29H38O3 |
| Molar mass | 434.610 g/mol g·mol−1 |
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See also
References
- 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.
- George W.A Milne (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1577–. ISBN 978-1-351-78989-9.
- 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.
- 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
- 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.
- Petrow V (1970). "The contraceptive progestagens". Chem. Rev. 70 (6): 713–26. doi:10.1021/cr60268a004. PMID 4098492.
- Goldsmith, A., & Toppozada, M. (1983). Long-acting contraception. pp. 94-95 https://www.popline.org/node/423289
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