QuickView for Levonorgestrel (compound)

Summary
General Info

PubChem

PubChem Compound 10335940

Name:	Levonorgestrel
PubChem Compound ID:	10335940
Description:	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.
Molecular formula:	C₂₁H₂₈O₂
Molecular weight:	316.462 g/mol

DrugBank

Identification

Name:	Levonorgestrel
Name (isomeric):	DB00367
Drug Type:	small molecule
Description:	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.
Synonyms:	SOH-075; Levonorgestrelum [INN-Latin]
Brand:	Tri-Levlen 21, Nordette 21, Levonelle, Trinordiol 21, Microgynon Cd, Ovral-Lo, Microgynon 30 Ed, Trinordiol 28, Norplant 2, Levora-28, Trifeme 28, Microgest Ed, Stediril 30, Malloside, Neogynon 21, Trigoa, Levora-21, Triciclor, Norplant II, Postinor-2, NorLevo, Logynon Ed, Ovrette, Microgynon 21, Triagynon, Nordette 28, Jadelle, Microlution, Minivlar 30, Microgynon 28, Levonova, Microval, Mirena, Nordet, Plan B, Follistrel, Levlen Ed, Monofeme 28, Rigevidon 21+7, Ovranette, Norplant, Levlen, Trivora, Tri-Levlen, 72-HOURS, Nordette, Microgyn
Brand name mixture:	Triquilar 21 Tab(Ethinyl Estradiol + Levonorgestrel), Triphasil 28 Tab(Ethinyl Estradiol + Levonorgestrel), Alesse 21 Tablets(Ethinyl Estradiol + Levonorgestrel), Alesse 28 Tablets(Ethinyl Estradiol + Levonorgestrel), Min-Ovral 21 Tab(Ethinyl Estradiol + Levonorgestrel), Min-Ovral 21(Ethinyl Estradiol + Levonorgestrel), Min-Ovral 28 Tab(Ethinyl ... show more » Triquilar 21 Tab(Ethinyl Estradiol + Levonorgestrel), Triphasil 28 Tab(Ethinyl Estradiol + Levonorgestrel), Alesse 21 Tablets(Ethinyl Estradiol + Levonorgestrel), Alesse 28 Tablets(Ethinyl Estradiol + Levonorgestrel), Min-Ovral 21 Tab(Ethinyl Estradiol + Levonorgestrel), Min-Ovral 21(Ethinyl Estradiol + Levonorgestrel), Min-Ovral 28 Tab(Ethinyl Estradiol + Levonorgestrel), Triquilar 28 Tab(Ethinyl Estradiol + Levonorgestrel), Preven Tablets(Ethinyl Estradiol + Levonorgestrel), Triphasil 21(Ethinyl Estradiol + Levonorgestrel), Triphasil 28(Ethinyl Estradiol + Levonorgestrel), Min-Ovral 28(Ethinyl Estradiol + Levonorgestrel), Triphasil 21 Tab(Ethinyl Estradiol + Levonorgestrel) show less «
Category:	Contraceptive Agents, Female, Contraceptives, Oral, Synthetic, Contraceptives
CAS number:	797-63-7

Pharmacology

Indication:	For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive.
Pharmacology:	Levonorgestrel 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 ... show more » Levonorgestrel 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. Levonorgestrel 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:	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 levonorgestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (lut... show more » 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 levonorgestrel 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:	Levonorgestrel is not subjected to a "first-pass" effect and is virtually 100% bioavailable.
Protein binding:	55%
Biotransformation:	Hepatic
Route of elimination:	About 45% of levonorgestrel and its metabolites are excreted in the urine and about 32% are excreted in feces, mostly as glucuronide conjugates.
Clearance:	7.7 +/- 2.7 L/h [Healthy Female Volunteers under Fasting Conditions]
Toxicity:	LD₅₀>5000 mg/kg (orally in rats)
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:

Ethotoin	Phenytoin decreases the contraceptive effect
Talbutal	Phenobarbital decreases the effect of levonorgestrel
Phenytoin	Phenytoin decreases the contraceptive effect
Methohexital	Phenobarbital decreases the effect of levonorgestrel
Warfarin	Levonorgestrel may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if levonorgestrel is initiated, discontinued or dose changed.

Ethotoin	Phenytoin decreases the contraceptive effect
Talbutal	Phenobarbital decreases the effect of levonorgestrel
Phenytoin	Phenytoin decreases the contraceptive effect
Methohexital	Phenobarbital decreases the effect of levonorgestrel
Warfarin	Levonorgestrel may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if levonorgestrel is initiated, discontinued or dose changed.
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.
Tretinoin	Oral Tretinoin may decrease the effect of oral contraceptive, Levonorgestrel. An alternate form of contraception should be used during concomitant therapy.
Secobarbital	Phenobarbital decreases the effect of levonorgestrel
Butalbital	Phenobarbital decreases the effect of levonorgestrel
Artemether	Artemether may decrease the effectiveness of levonorgestrel by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Phenobarbital	Phenobarbital decreases the effect of levonorgestrel
Bexarotene	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of levonorgestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Pentobarbital	Phenobarbital decreases the effect of levonorgestrel
Methylphenobarbital	Phenobarbital decreases the effect of levonorgestrel
Primidone	Phenobarbital decreases the effect of levonorgestrel
Amobarbital	Phenobarbital decreases the effect of levonorgestrel
Heptabarbital	Phenobarbital decreases the effect of levonorgestrel
Butethal	Phenobarbital decreases the effect of levonorgestrel
Thiopental	Thiopental may decrease the effect of Levonorgestrel. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Fosphenytoin	Phenytoin decreases the contraceptive effect
Dihydroquinidine barbiturate	Phenobarbital decreases the effect of levonorgestrel
Mephenytoin	Phenytoin decreases the contraceptive effect
Aprobarbital	Phenobarbital decreases the effect of levonorgestrel
Hexobarbital	Phenobarbital decreases the effect of levonorgestrel
Carbamazepine	Carbamazepine may decrease the contraceptive effect of levonorgestrel.
Butabarbital	Phenobarbital decreases the effect of levonorgestrel
Quinidine barbiturate	Phenobarbital decreases the effect of levonorgestrel

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Targets

Progesterone receptor

3-oxo-5-alpha-steroid 4-dehydrogenase 1

Enzymes