Levonorgestrel cyclopropylcarboxylate

Levonorgestrel cyclopropylcarboxylate (developmental code name HRP-003), or levonorgestrel 17β-cyclopropylcarboxylate, 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 cyclopropylcarboxylate include levonorgestrel cyclobutylcarboxylate (HRP-001) and levonorgestrel butanoate (HRP-002).[1][2][3]

Levonorgestrel cyclopropylcarboxylate

Clinical data
Other names	HRP-003; HRP003; Levonorgestrel cyclopropyl-carboxylate; Levonorgestrel 17β-cyclopropylcarboxylate; 17α-Ethynyl-18-methyl-19-nortestosterone 17β-cyclopropylcarboxylate; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 17β-cyclopropylcarboxylate; 13-Ethyl-17α-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one cyclopropanecarboxylate
Routes of administration	Intramuscular injection
Drug class	Progestogen; Progestin; Progestogen ester
Identifiers
IUPAC name [(8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] cyclopropanecarboxylate
CAS Number	86679-35-8
PubChem CID	10317658
ChemSpider	8493122
Chemical and physical data
Formula	C25H32O3
Molar mass	380.528 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)OC(=O)C4CC4)CCC5=CC(=O)CC[C@H]35
InChI InChI=1S/C25H32O3/c1-3-24-13-11-20-19-10-8-18(26)15-17(19)7-9-21(20)22(24)12-14-25(24,4-2)28-23(27)16-5-6-16/h2,15-16,19-22H,3,5-14H2,1H3/t19-,20+,21+,22-,24-,25-/m0/s1 Key:TZZXNSUFTUXHRE-AYEDEZQKSA-N

See also

• List of progestogen esters § Esters of 19-nortestosterone derivatives
• Progestogen-only injectable contraceptive

References

1. Benagiano, G., & Merialdi, M. (2011). Carl Djerassi and the World Health Organisation special programme of research in human reproduction. Journal für Reproduktionsmedizin und Endokrinologie-Journal of Reproductive Medicine and Endocrinology, 8(1), 10-13. http://www.kup.at/kup/pdf/10163.pdf
2. Garza-Flores J, Hall PE, Perez-Palacios G (1991). "Long-acting hormonal contraceptives for women". J. Steroid Biochem. Mol. Biol. 40 (4–6): 697–704. doi:10.1016/0960-0760(91)90293-E. PMID 1958567. S2CID 26021562.
3. Wu L, Janagam DR, Mandrell TD, Johnson JR, Lowe TL (July 2015). "Long-acting injectable hormonal dosage forms for contraception". Pharm. Res. 32 (7): 2180–91. doi:10.1007/s11095-015-1686-2. PMID 25899076. S2CID 12856674.
4. 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.
5. Marcus Filshie; John Guillebaud (22 October 2013). Contraception: Science and Practice. Elsevier Science. pp. 112–. ISBN 978-1-4831-6366-6.
6. Elizabeth Connell (4 December 2001). The Contraception Sourcebook. McGraw Hill Professional. p. 133. ISBN 978-0-07-139945-6.
7. Gerald I. Zatuchni; Northwestern University (Evanston, Ill.). Program for Applied Research on Fertility Regulation (1984). 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.
8. Egon Diczfalusy (1987). Fertility regulation today and tomorrow. Raven Press. p. 132. ISBN 978-0-88167-180-3.
9. Seiichi Matsumoto; Japan Family Planning Association (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.
10. L. R. Sitruk-Ware; C. Wayne Bardin (1992). Contraception: newer pharmacological agents, devices, and delivery systems. M. Dekker. p. 62. ISBN 978-0-8247-8700-4.