Levonorgestrel cyclobutylcarboxylate

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]

Levonorgestrel cyclobutylcarboxylate
Clinical data
Other namesHRP-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 classProgestogen; 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] cyclobutanecarboxylate
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.081.126
Chemical and physical data
FormulaC26H34O3
Molar mass394.555 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)OC(=O)C4CCC4)CCC5=CC(=O)CC[C@H]35
InChI
  • InChI=1S/C26H34O3/c1-3-25-14-12-21-20-11-9-19(27)16-18(20)8-10-22(21)23(25)13-15-26(25,4-2)29-24(28)17-6-5-7-17/h2,16-17,20-23H,3,5-15H2,1H3/t20-,21+,22+,23-,25-,26-/m0/s1
  • Key:WWGTWFPUIPEHNX-UKNJCJGYSA-N

See also

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.



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