4804
T3D4749
Levonorgestrel
A synthetic progestational hormone with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Levonorgestrel is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Triphasil, and Min-Ovral.
797-63-7
13109
C21H28O2
White powder.
240°C
2.05 mg/L
Levonorgestrel is not subjected to a "first-pass" effect and is virtually 100% bioavailable.
Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like levonorgestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.
Hepatic.
Route of Elimination: About 45% of levonorgestrel and its metabolites are excreted in the urine and about 32% are excreted in feces, mostly as glucuronide conjugates.
LD50 >5000 mg/kg (orally in rats)
Norgestrel: Group 2B, possibly carcinogenic to humans. (L135)
For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive.
2014-09-11T05:14:42Z
2014-12-24T20:26:56Z
Levonorgestrel
C08149
6443
DB00367
NOG
true
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
C21H28O2
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChIKey=WWYNJERNGUHSAO-XUDSTZEESA-N
312.4458
312.20893014
Exogenous
Solid
3.8
HMDB14511
CHEMBL1389
12560
<p>Yu-Sheng Chang, Shu-Ping Chen, “Levonorgestrel Crystallization.” U.S. Patent US20090069584, issued March 12, 2009.</p>