Levonorgestrel acetate Other names LNG-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 class Progestogen ; 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] acetate
CAS Number PubChem CID ChemSpider UNII ECHA InfoCard 100.123.252 Formula C 23 H 30 O 3 Molar mass 354.490 g·mol−1 3D model (JSmol )
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=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
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]
See also [ ]
References [ ]
^ a b 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 .
^ a b c d 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 .
^ a b 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 .
^ a b 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 .
^ 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 .
^ 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).
AR
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Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids
PR
Agonists
Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
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Receptor/signaling modulators
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Estrogen receptor modulators
List of progestogens