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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O2
Molecular Weight 312.4458
Optical Activity ( - )
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVONORGESTREL

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=WWYNJERNGUHSAO-XUDSTZEESA-N
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

HIDE SMILES / InChI

Molecular Formula C21H28O2
Molecular Weight 312.4458
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Levonorgestrel (LNG) is 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. Within an Intrauterine device (IUD), sold as Mirena among others, it is effective for long term prevention of pregnancy. The local mechanism by which continuously released LNG enhances contraceptive effectiveness of Mirena has not been conclusively demonstrated. Studies of Mirena and similar LNG IUS prototypes have suggested several mechanisms that prevent pregnancy: thickening of cervical mucus preventing passage of sperm into the uterus, inhibition of sperm capacitation or survival, and alteration of the endometrium. Mirena has mainly local progestogenic effects in the uterine cavity. The high local levels of levonorgestrel lead to morphological changes including stromal pseudodecidualization, glandular atrophy, a leukocytic infiltration and a decrease in glandular and stromal mitoses. Ovulation is inhibited in some women using Mirena. In a 1-year study, approximately 45% of menstrual cycles were ovulatory, and in another study after 4 years, 75% of cycles were ovulatory. There has been much debate regarding levonorgestrel emergency contraception's (LNG-EC's) method of action since 1999 when the Food and Drug Administration first approved its use. Proponents of LNG-EC have argued that they have moral certitude that LNG-EC works via a non-abortifacient mechanism of action, and claim that all the major scientific and medical data consistently support this hypothesis. However, newer medical data serve to undermine the consistency of the non-abortifacient hypothesis and instead support the hypothesis that preovulatory administration of LNG-EC has significant potential to work via abortion. The implications of the newer data have important ramifications for medical personnel, patients, and both Catholic and non-Catholic emergency room protocols. In the future, technology such as the use of early pregnancy factor may have the potential to quantify how frequently preovulatory LNG-EC works via abortion. The latest scientific and medical evidence now demonstrates that levonorgestrel emergency contraception theoretically works via abortion quite often. The implications of the newer data have important ramifications for medical personnel, patients, and both Catholic and non-Catholic emergency room rape protocols.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
MIRENA
Primary
MIRENA
Preventing
OVRETTE
Preventing
ELINEST

Cmax

ValueDoseCo-administeredAnalytePopulation
14.11 ng/mL
0.75 mg single, oral
LEVONORGESTREL plasma
Homo sapiens
16.2 ng/mL
1.5 mg single, oral
LEVONORGESTREL blood
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
123.1 ng × h/mL
0.75 mg single, oral
LEVONORGESTREL plasma
Homo sapiens
360.1 ng × h/mL
1.5 mg single, oral
LEVONORGESTREL blood
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
24.4 h
0.75 mg single, oral
LEVONORGESTREL plasma
Homo sapiens
29.7 h
1.5 mg single, oral
LEVONORGESTREL blood
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
OVRETTE tablets (0.075 mg norgestrel) are available in packages of 6 PILPAK dispensers with 28 tablets each as follows: NDC 0008-0062-01, yellow, round tablet marked "WYETH" on one side and "62" on reverse side. To achieve maximum contraceptive effectiveness, OVRETTE must be taken exactly as directed. One tablet is taken every day, at the same time. Administration is continuous, with no interruption between pill packs.
Route of Administration: Oral
In Vitro Use Guide
Norgestrel stimulated MCF-7 cell proliferation at a concentration of 10(-8) M.
Substance Class Chemical
Record UNII
5W7SIA7YZW
Record Status Validated (UNII)
Record Version