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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

CC[C@]12CC(=C)[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C

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

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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
IMPLANON
PubMed

PubMed

TitleDatePubMed
Effect on insulin sensitivity of Implanon vs. GnRH agonist in women with endometriosis.
2005 Dec
Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells.
2005 Dec
How to remove impalpable Implanon implants.
2005 Oct
An assessment of the first 3 years' use of Implanon in Luton.
2005 Oct
[Ectopic pregnancy with etonogestrel contraceptive implant (Implanon): first case].
2005 Oct
[Hormonal contraception for males--an option for adolescents?].
2005 Oct
Transitory reduction of platelet aggregation with the use of etonogestrel implant in healthy women.
2005 Sep
A pilot study to assess the effect of three short-term treatments on frequent and/or prolonged bleeding compared to placebo in women using Implanon.
2006 Jan
Failure of Implanon contraception in a patient taking carbamazepin for epilepsia.
2006 Jan
A multicentre study investigating subcutaneous etonogestrel implants with injectable testosterone decanoate as a potential long-acting male contraceptive.
2006 Jan
Patents

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
Name Type Language
ETONOGESTREL
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
ETONOGESTREL [MI]
Common Name English
ORG 3236
Code English
ETONOGESTREL [INN]
Common Name English
DESOGESTREL IMPURITY D
EP  
Common Name English
ETONOGESTREL [WHO-DD]
Common Name English
13-ETHYL-17-HYDROXY-11-METHYLENE-18,19-DINOR-17.ALPHA.-PREGN-4-EN-20-YN-3-ONE
Common Name English
ETONOGESTREL [ORANGE BOOK]
Common Name English
ETONOGESTREL [USAN]
Common Name English
NUVARING COMPONENT ETONOGESTREL
Common Name English
IMPLANON
Brand Name English
ORG-3236
Code English
ETONOGESTREL [MART.]
Common Name English
ETONOGESTREL [VANDF]
Common Name English
DESOGESTREL RELATED COMPOUND C [USP-RS]
Common Name English
DESOGESTREL IMPURITY D [EP]
Common Name English
18,19-DINOR-17.ALPHA.-PREGN-4-EN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-11-METHYLENE-
Common Name English
DESOGESTREL RELATED COMPOUND C
USP-RS  
Common Name English
DESOGESTREL SPECIFIED IMPURITY D [EP]
Common Name English
ETONOGESTREL COMPONENT OF NUVARING
Common Name English
Classification Tree Code System Code
NDF-RT N0000011301
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
WHO-ATC G03AC08
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
WHO-VATC QG03AC08
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
LIVERTOX 388
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
NDF-RT N0000175602
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
Code System Code Type Description
ChEMBL
CHEMBL1531
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
RXCUI
14584
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY RxNorm
IUPHAR
7590
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
NCI_THESAURUS
C47528
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
ECHA (EC/EINECS)
258-936-2
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
INN
6832
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
MERCK INDEX
M5198
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY Merck Index
EVMPD
SUB07335MIG
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
DRUG BANK
DB00294
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
LactMed
54048-10-1
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
CAS
54048-10-1
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
EPA CompTox
54048-10-1
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
WIKIPEDIA
ETONOGESTREL
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY
PUBCHEM
6917715
Created by admin on Tue Mar 06 10:32:15 UTC 2018 , Edited by admin on Tue Mar 06 10:32:15 UTC 2018
PRIMARY SWITZERF