Levonorgestrel cyclobutylcarboxylate (or levonorgestrel 17β-cyclobutylcarboxylate; developmental code name HRP-001) is a progestin and a progestogen ester which was studied for potential use as an injectable hormonal contraceptive but was never marketed.[1][2][3][4][5][6][7][8][9][10] It was developed by the World Health Organization's Special Programme on Human Reproduction in the 1980s.[1][2][9] Analogues of levonorgestrel cyclobutylcarboxylate include levonorgestrel butanoate (HRP-002) and levonorgestrel cyclopropylcarboxylate (HRP-003).[1][2][3]
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| Other names | HRP-001; HRP001; Levonorgestrel cyclobutyl-carboxylate; Levonorgestrel cyclobutanecarboxylate; Levonorgestrel 17β-cyclobutylcarboxylate; 17α-Ethynyl-18-methyl-19-nortestosterone 17β-cyclobutylcarboxylate; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 17β-cyclobutylcarboxylate; 13-Ethyl-17α-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one cyclobutanecarboxylate |
| Routes of administration | Intramuscular injection |
| Drug class | Progestogen; Progestin; Progestogen ester |
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| ECHA InfoCard | 100.081.126 |
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| Formula | C26H34O3 |
| Molar mass | 394.555 g·mol−1 |
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See also
editReferences
edit- ^ a b c Benagiano G, Merialdi M (2011). "Carl Djerassi and the World Health Organisation special programme of research in human reproduction" (PDF). Journal für Reproduktionsmedizin und Endokrinologie-Journal of Reproductive Medicine and Endocrinology. 8 (1): 10–13.
- ^ a b c Garza-Flores J, Hall PE, Perez-Palacios G (1991). "Long-acting hormonal contraceptives for women". The Journal of Steroid Biochemistry and Molecular Biology. 40 (4–6): 697–704. doi:10.1016/0960-0760(91)90293-E. PMID 1958567. S2CID 26021562.
- ^ a b Wu L, Janagam DR, Mandrell TD, Johnson JR, Lowe TL (July 2015). "Long-acting injectable hormonal dosage forms for contraception". Pharmaceutical Research. 32 (7): 2180–2191. doi:10.1007/s11095-015-1686-2. PMID 25899076. S2CID 12856674.
- ^ Runnebaum B, Rabe T, Kiesel L (1988). "Trends in Hormonal Contraception". Female Contraception. pp. 109–121. doi:10.1007/978-3-642-73790-9_9. ISBN 978-3-642-73792-3.
- ^ Fraser IS (22 October 2013). "Systemic hormonal contraception by non-oral routes". In Filshie M, Guillebaud J (eds.). Contraception: Science and Practice. Elsevier Science. pp. 112–. ISBN 978-1-4831-6366-6.
- ^ Connell E (4 December 2001). The Contraception Sourcebook. McGraw Hill Professional. p. 133. ISBN 978-0-07-139945-6.
- ^ Hall PE, Bialy G, Blye RP, Crabbé P (1984). "Development of Levonorgestrel Esters as Long-Acting Injectable Contraceptives". In Zatuchni GI (ed.). Long-Acting Contraceptive Delivery Systems: Proceedings of an International Workshop on Long-Acting Contraceptive Delivery Systems, May 31-June 3, 1983, New Orleans, Louisiana. Harper & Row Pub. p. 196. ISBN 978-0-06-142905-7.
- ^ Diczfalusy E (1987). Fertility regulation today and tomorrow. Raven Press. p. 132. ISBN 978-0-88167-180-3.
- ^ a b Matsumoto S, ed. (1987). Recent advances in fertility control: proceedings of the 1st International Symposium on Recent Advances in Fertility Control, Tokyo, November 8, 1986. Excerpta Medica. p. 67. ISBN 978-90-219-1638-5.
- ^ Sitruk-Ware LR, Bardin CW, eds. (1992). Contraception: newer pharmacological agents, devices, and delivery systems. M. Dekker. p. 62. ISBN 978-0-8247-8700-4.
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