Drug/Small Molecule:
levonorgestrel

2D structure

Overview

Generic Names: Levonorgestrelum [INN-Latin]; SOH-075
Trade Names: 72-HOURS; Follistrel; Jadelle; Levlen; Levlen Ed; Levonelle; Levonova; Levora-21; Levora-28; Logynon Ed; Malloside; Microgest Ed; Microgyn; Microgynon 21; Microgynon 28; Microgynon 30 Ed; Microgynon Cd; Microlution; Microval; Minivlar 30; Mirena; Monofeme 28; Neogynon 21; NorLevo; Nordet; Nordette; Nordette 21; Nordette 28; Norplant; Norplant 2; Norplant II; Ovral-Lo; Ovranette; Ovrette; Plan B; Postinor-2; Stediril 30; Tri-Levlen; Tri-Levlen 21; Triagynon; Triciclor; Trifeme 28; Trigoa; Trinordiol 21; Trinordiol 28; Trivora
Brand Mixtures: Alesse 21 Tablets (Ethinyl Estradiol + Levonorgestrel); Alesse 28 Tablets (Ethinyl Estradiol + Levonorgestrel); Min-Ovral 21 (Ethinyl Estradiol + Levonorgestrel); Min-Ovral 21 Tab (Ethinyl Estradiol + Levonorgestrel); Min-Ovral 28 (Ethinyl Estradiol + Levonorgestrel); Min-Ovral 28 Tab (Ethinyl Estradiol + Levonorgestrel); Preven Tablets (Ethinyl Estradiol + Levonorgestrel); Rigevidon 21+7; Triphasil 21 (Ethinyl Estradiol + Levonorgestrel); Triphasil 21 Tab (Ethinyl Estradiol + Levonorgestrel); Triphasil 28 (Ethinyl Estradiol + Levonorgestrel); Triphasil 28 Tab (Ethinyl Estradiol + Levonorgestrel); Triquilar 21 Tab (Ethinyl Estradiol + Levonorgestrel); Triquilar 28 Tab (Ethinyl Estradiol + Levonorgestrel)
PharmGKB Accession Id: PA450218

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. PubChem (source: Drug Bank)

Indication

For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive. (source: Drug Bank)

ATC Therapeutic Categories

  • G02BA:Intrauterine contraceptives
  • G03AC:Progestogens

Pharmacology, Interactions, and Contraindications

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 (luteinizing hormone) surge. (source: Drug Bank)

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 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. (source: Drug Bank)

Food Interactions

Avoid alcohol.
Avoid excessive quantities of coffee or tea (Caffeine).
Increase dietary intake of magnesium, folate, vitamin B6, B12, and/or consider taking a multivitamin.
Take at the same time everyday.
Take with food. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (source: Drug Bank)

Protein Binding

55% (source: Drug Bank)

Absorption

Levonorgestrel is not subjected to a "first-pass" effect and is virtually 100% bioavailable. (source: Drug Bank)

Toxicity

LD<sub>50</sub>>5000 mg/kg (orally in rats) (source: Drug Bank)

Isomeric SMILES Code:

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

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
ACSL1
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
AR
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Publications
Phenotype data available No genotype data Literature annotations available Not annotated
ATP1A1
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
ATP1B1
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  • PD
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
BCL6
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  • PD
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
C7orf68
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  • PD
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Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
CRP
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
CXCL12
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Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
HSD11B2
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
KLF4
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No phenotype data No genotype data Literature annotations available Not annotated
NET1
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
PGR
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No phenotype data No genotype data Literature annotations available Not annotated
PPL
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No phenotype data No genotype data Literature annotations available Not annotated
S100P
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No phenotype data No genotype data Literature annotations available Not annotated
TSC22D3
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Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
VCAM1
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  • PD
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Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
ESR1 Uncurated Annotation (source: Drug Bank)
PGR Uncurated Annotation (source: Drug Bank)

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
amobarbital Uncurated Annotation Phenobarbital decreases the effect of levonorgestrel (source: Drug Bank)
butalbital Uncurated Annotation Phenobarbital decreases the effect of levonorgestrel (source: Drug Bank)
carbamazepine Uncurated Annotation Carbamazepine decreases the contraceptive effect (source: Drug Bank)
hexobarbital Uncurated Annotation Phenobarbital decreases the effect of levonorgestrel (source: Drug Bank)
mephenytoin Uncurated Annotation Phenytoin decreases the contraceptive effect (source: Drug Bank)
methylphenobarbital Uncurated Annotation Phenobarbital decreases the effect of levonorgestrel (source: Drug Bank)
pentobarbital Uncurated Annotation Phenobarbital decreases the effect of levonorgestrel (source: Drug Bank)
phenobarbital Uncurated Annotation Phenobarbital decreases the effect of levonorgestrel (source: Drug Bank)
phenytoin Uncurated Annotation Phenytoin decreases the contraceptive effect (source: Drug Bank)
primidone Uncurated Annotation Phenobarbital decreases the effect of levonorgestrel (source: Drug Bank)

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Colorectal Neoplasms
  • CO
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Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00367
KEGG Compound ID:
C08149
KEGG Drug ID:
D00950
PubChem Compound ID:
13109
PubChem Substance ID:
10349

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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