QuickView for etonogestrel (compound)

Summary
General Info

PubChem

PubChem Compound 40976

Name:	3-keto-desogestrel
PubChem Compound ID:	40976
Molecular formula:	C₂₂H₂₈O₂
Molecular weight:	324.457 g/mol
Synonyms:	ORG 3236; EINECS 258-936-2; 3-Keto-desogestrel; 3-Oxodesogestrel; 13-Ethyl-11-methylene-18,19-dinor-17-alpha-pregn-4-en-20-yn-3-one; (17alpha)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one; 54048-10-1; 18,19-Dinor-17alpha-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-; 3-Ketodesogestrel; 13-Ethyl-17-hydroxy-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one. show more » ORG 3236; EINECS 258-936-2; 3-Keto-desogestrel; 3-Oxodesogestrel; 13-Ethyl-11-methylene-18,19-dinor-17-alpha-pregn-4-en-20-yn-3-one; (17alpha)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one; 54048-10-1; 18,19-Dinor-17alpha-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-; 3-Ketodesogestrel; 13-Ethyl-17-hydroxy-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one; 165050-21-5; Etonogestrel; 18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-, (17-alpha)-; Implanon; 17-Ethinyl-17-beta-hydroxy-18-methyl-11-methylene-4-estren-3-one; (17-alpha)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one; Etonogestrel [USAN:INN] show less «

DrugBank

Identification

Name:	3-keto-desogestrel
Name (isomeric):	DB00294
Drug Type:	small molecule
Brand:	Implanon
Brand name mixture:	Nuvaring(Ethinyl Estradiol + Etonogestrel)
Category:	Contraceptive Agents, Female, Contraceptives
CAS number:	54048-10-1

Pharmacology

Indication:	For use as a female contraceptive (depot).
Pharmacology:	Etonogestrel is used as a female contraceptive. 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 li... show more » Etonogestrel is used as a female contraceptive. 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. show less «
Mechanism of Action:	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-ovulat... show more » 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. show less «
Biotransformation:	Hepatic.
Route of elimination:	Excretion of ENG and its metabolites, either as free steroid or as conjugates, is mainly in urine and to a lesser extent in feces.
Half Life:	25 hours
Toxicity:	Symptoms of overdose include nausea, vomiting, vaginal bleeding, and other menstrual irregularities.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Avoid alcohol.

Increase dietary intake of magnesium, folate, vitamin B6, B12, and/or consider taking a multivitamin.

Avoid excessive quantities of coffee or tea (Caffeine).

Take with food.

Take at the same time everyday.

Drug interaction:

Warfarin	Etonogestrel may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if etonogestrel is initiated, discontinued or dose changed.
Thiopental	Thiopental may decrease the effect of Etonogestrel. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Artemether	Artemether may decrease the effectiveness of etonogestrel by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Tretinoin	Oral Tretinoin may decrease the effect of oral contraceptive, Etonogestrel. An alternate form of contraception should be used during concomitant therapy.
Colesevelam	Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Progestins). Administer oral progestin-containing contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness.

Targets

Progesterone receptor

Estrogen receptor

Enzymes

Cytochrome P450 3A4