levonorgestrel cyclopropylcarboxylate

{{Short description|Chemical compound}}

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| 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

| image = Levonorgestrel cyclopropylcarboxylate.svg

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| routes_of_administration = Intramuscular injection

| class = Progestogen; Progestin; Progestogen ester

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| CAS_number = 86679-35-8

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| PubChem = 10317658

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| ChemSpiderID = 8493122

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| synonyms = 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

| C=25 | H=32 | O=3

| 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

| StdInChI_Ref =

| StdInChI = 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

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| StdInChIKey = TZZXNSUFTUXHRE-AYEDEZQKSA-N

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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.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{{cite journal | vauthors = Garza-Flores J, Hall PE, Perez-Palacios G | title = Long-acting hormonal contraceptives for women | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 40 | issue = 4–6 | pages = 697–704 | date = 1991 | pmid = 1958567 | doi = 10.1016/0960-0760(91)90293-E | s2cid = 26021562 }}{{cite journal | vauthors = Wu L, Janagam DR, Mandrell TD, Johnson JR, Lowe TL | title = Long-acting injectable hormonal dosage forms for contraception | journal = Pharmaceutical Research | volume = 32 | issue = 7 | pages = 2180–2191 | date = July 2015 | pmid = 25899076 | doi = 10.1007/s11095-015-1686-2 | s2cid = 12856674 }}{{cite book| vauthors = Runnebaum B, Rabe T, Kiesel L |title=Female Contraception|chapter=Trends in Hormonal Contraception|year=1988|pages=109–121|doi=10.1007/978-3-642-73790-9_9|isbn=978-3-642-73792-3}}{{cite book| vauthors = Filshie M, Guillebaud J |title=Contraception: Science and Practice|url=https://books.google.com/books?id=Ug3-BAAAQBAJ&pg=PA112|date=22 October 2013|publisher=Elsevier Science|isbn=978-1-4831-6366-6|pages=112–}}{{cite book| vauthors = Connell E |title=The Contraception Sourcebook|url=https://books.google.com/books?id=HWoWwGwlEcUC|date=4 December 2001|publisher=McGraw Hill Professional|isbn=978-0-07-139945-6|page=133}}{{cite book| vauthors = Zatuchni GI | collaboration = Program for Applied Research on Fertility Regulation|title=Long-Acting Contraceptive Delivery Systems: Proceedings of an International Workshop on Long-Acting Contraceptive Delivery Systems, May 31-June 3, 1983, New Orleans, Louisiana|url=https://books.google.com/books?id=QKtsAAAAMAAJ|year=1984|publisher=Harper & Row Pub.|isbn=978-0-06-142905-7|page=196}}{{cite book| vauthors = Diczfalusy E |title=Fertility regulation today and tomorrow|url=https://books.google.com/books?id=-GJqAAAAMAAJ|year=1987|publisher=Raven Press|isbn=978-0-88167-180-3|page=132}}{{cite book| vauthors = Matsumoto S | collaboration =Japan Family Planning Association|title=Recent advances in fertility control: proceedings of the 1st International Symposium on Recent Advances in Fertility Control, Tokyo, November 8, 1986|url=https://books.google.com/books?id=X6tsAAAAMAAJ|year=1987|publisher=Excerpta Medica|isbn=978-90-219-1638-5|page=67}}{{cite book| vauthors = Sitruk-Ware LR, Bardin CW |title=Contraception: newer pharmacological agents, devices, and delivery systems|url=https://books.google.com/books?id=L5NsAAAAMAAJ|year=1992|publisher=M. Dekker|isbn=978-0-8247-8700-4|page=62}} It was developed by the World Health Organization's Special Programme on Human Reproduction in the 1980s. Analogues of levonorgestrel cyclopropylcarboxylate include levonorgestrel cyclobutylcarboxylate (HRP-001) and levonorgestrel butanoate (HRP-002).