From Wikipedia, the free encyclopedia
Chemical compound
Levonorgestrel cyclobutylcarboxylate
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
[(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 InfoCard
100.081.126
Formula C 26 H 34 O 3
Molar mass 394.555 g·mol−1 3D model (
JSmol )
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=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
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]
See also
References
^
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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