QuickView for Norgestrel (compound)

Summary
General Info

PubChem

PubChem Compound 4542

Name:	Norgestrel
PubChem Compound ID:	4542
Description:	A synthetic progestational agent with actions similar to those of PROGESTERONE. This racemic or (+-)-form has about half the potency of the levo form (LEVONORGESTREL). Norgestrel is used as a contraceptive, ovulation inhibitor, and for the control of menstrual disorders and endometriosis.
Molecular formula:	C₂₁H₂₈O₂
Molecular weight:	312.446 g/mol
Synonyms:	Norgestrel; 18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17.alpha.)-(.+/-.)-

DrugBank

Identification

Name:	Norgestrel
Name (isomeric):	DB00506
Drug Type:	small molecule
Description:	A synthetic progestational agent with actions similar to those of PROGESTERONE. This racemic or (+-)-form has about half the potency of the levo form (LEVONORGESTREL). Norgestrel is used as a contraceptive, ovulation inhibitor, and for the control of menstrual disorders and endometriosis.
Brand:	Stediril, Microlut, NOG, Ovral, Alpha-Norgestrel, Alesse, LD Norgestrel, Norgeston, Ovran, Trinordiol, Component of Lo/Ovral, Tetragynon, Neogest, Component of Ovral, Microgynon, Norgestrelum [INN-Latin], Norgestrel [Progestins], Ld Norgestrel [French], DL-Norgestrel, Methylnorethindrone, Postinor, Lo/Ovral, Logynon, Monovar, Norgestrel [Usan:Ban:Inn:Jan]
Brand name mixture:	Lo-Femenal 21 Tablets(ethinyl estradiol + norgestrel), Ovral 21 Tablets(ethinyl estradiol + norgestrel), Ovral 28 Tablets(ethinyl estradiol + norgestrel)
Category:	Contraceptive Agents, Female, Contraceptives, Oral, Synthetic, Contraceptives
CAS number:	6533-00-2

Pharmacology

Indication:	Used as an oral contraceptive to prevent pregnancy
Pharmacology:	Norgestrel is used as a female contraceptive. Norgestrel 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... show more » Norgestrel is used as a female contraceptive. Norgestrel 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. Norgestrel 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:	Norgestrel 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 Norgestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory ... show more » Norgestrel 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 Norgestrel 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 «
Absorption:	65%
Protein binding:	Norgestrel-binding protein in the plasma appeared to be a protein different from human serum albumin, corticosteroid-binding globulin and sex-steroid-binding protein. High binding (>95%).
Biotransformation:	Hepatic
Half Life:	5-14 hours
Toxicity:	Nausea, vomiting, and drowsiness/fatigue; Withdrawal bleeding; LD₅₀=mg/kg (orally in rat)
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:

Artemether	Artemether may decrease the effectiveness of norgestrel by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Warfarin	Norgestrel may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if norgestrel is initiated, discontinued or dose changed.
Thiopental	Thiopental may decrease the effect of Norgestrel. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Bexarotene	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norgestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Tretinoin	Oral Tretinoin may decrease the effect of oral contraceptive, Norgestrel. An alternate form of contraception should be used during concomitant therapy.

Targets

Progesterone receptor

Estrogen receptor

Enzymes

Cytochrome P450 3A4