Levonorgestrel acetate

Levonorgestrel acetate (LNG-A), or levonorgestrel 17β-acetate, also known as 3-ketonorgestimate, is a progestin which was never marketed.[1][2][3][4] It is a progestogen ester and is the C17β acetate ester and a prodrug of levonorgestrel.[2] Norgestimate is the C3 oxime of LNG-A.[1][5] The drug is a minor active metabolite of norgestimate, which is a prodrug of norelgestromin and to a lesser extent of levonorgestrel and LNG-A.[2] LNG-A has high affinity for the progesterone receptor, about 135% of that of promegestone (relative to 150% for levonorgestrel).[2][3] Along with levonorgestrel butanoate, LNG-A was investigated as a hormonal contraceptive by the Population Council.[6][4]

Levonorgestrel acetate
Clinical data
Other namesLNG-A; LNGA; 3-Ketonorgestimate; Levonorgestrel 17β-acetate; D-(–)-Norgestrel 17β-acetate; 17α-Ethynyl-18-methylestr-4-en-17β-ol-3-one 17β-acetate; 17β-Acetoxy-13β-ethyl-17α-ethynylgon-4-en-3-one
Drug classProgestogen; 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] acetate
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.123.252
Chemical and physical data
FormulaC23H30O3
Molar mass354.490 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)OC(=O)C)CCC4=CC(=O)CC[C@H]34
InChI
  • InChI=1S/C23H30O3/c1-4-22-12-10-19-18-9-7-17(25)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)26-15(3)24/h2,14,18-21H,4,6-13H2,1,3H3/t18-,19+,20+,21-,22-,23-/m0/s1
  • Key:YDQDJLTYVZAOQX-GOMYTPFNSA-N

See also

References
  1. Naderi S, Fotherby K (1983). "Long-acting contraceptive agents: in vitro hydrolysis of esters of norethisterone and levonorgestrel". Steroids. 41 (3): 397–417. doi:10.1016/0039-128x(83)90110-1. PMID 6419410. S2CID 28094296.
  2. Kuhl H (2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration" (PDF). Climacteric. 8 Suppl 1: 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  3. Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH (2008). "Classification and pharmacology of progestins". Maturitas. 61 (1–2): 171–80. doi:10.1016/j.maturitas.2008.11.013. PMID 19434889.
  4. Alvarez-Sanchez F, Brache V, Jackanicz T, Faundes A (1992). "Evaluation of four different contraceptive vaginal rings: steroid serum levels, luteal activity, bleeding control and lipid profiles". Contraception. 46 (4): 387–98. doi:10.1016/0010-7824(92)90101-x. PMID 1486777.
  5. Sven O. Skouby (15 July 1997). Clinical Perspectives on a New Gestodene Oral Contraceptive Containing 20μg of Ethinylestradiol. CRC Press. pp. 11–. ISBN 978-1-85070-786-8.
  6. Population Reports: Injectables and implants. Department of Medical and Public Affairs, George Washington University. 1987. The Population Council also plans to test vaginal rings with two other progestins, ST-1435 and levonorgestrel acetate, alone and combined with ethinyl estradiol (168).



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