U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28O2
Molecular Weight 324.4565
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETONOGESTREL

SMILES

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

InChI

InChIKey=GCKFUYQCUCGESZ-BPIQYHPVSA-N
InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H28O2
Molecular Weight 324.4565
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

Etonogestrel, also known as 11-methylenelevonorgestrel and 3-keto-desogestrel, is a steroidal progestin used in hormonal contraceptives, most notably the subdermal implants Nexplanon and Implanon and the vaginal ring NuvaRing. Etonogestrel is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Etonogestrel tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries. Etonogestrel 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 etonogestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
IMPLANON

Cmax

ValueDoseCo-administeredAnalytePopulation
0.59 ng/mL
75 μg 1 times / day multiple, oral
ETONOGESTREL serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
6.097 ng × h/mL
75 μg 1 times / day multiple, oral
ETONOGESTREL serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
29.2 h
75 μg 1 times / day multiple, oral
ETONOGESTREL serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
ETONOGESTREL blood
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Contraception One 68 mg implant inserted subdermally. The implant should not be left in place more than three years.
Route of Administration: Transdermal
In Vitro Use Guide
Etonogestrel (1716 pg/mL) significantly altered antiretroviral uptake across THP-1, BC-3 (CD8+) cell lines, incubated for one hour with tenofovir and emtricitabine to assess uptake except
Substance Class Chemical
Record UNII
304GTH6RNH
Record Status Validated (UNII)
Record Version