Drug/Small Molecule:
miconazole

2D structure

Overview

Generic Names: MCZ; miconazole
Trade Names: Daktarin; Femizol-M; M-zole 3 Combination Pack; M-zole 7 Dual Pack; Micatin; Miconazole 3; Miconazole 3 Combination Pack; Miconazole 7; Miconazole 7 Combination Pack; Miconazole Nitrate; Miconazole Nitrate Combination Pack; Miconazole-7; Micozole; Minostate; Monazole 7; Monistat; Monistat 1 Combination Pack; Monistat 3; Monistat 3 Combination Pack; Monistat 3 Dual-Pak; Monistat 3 Vaginal Ovules; Monistat 5; Monistat 5 Tampon; Monistat 7; Monistat 7 Combination Pack; Monistat 7 Dual-Pak; Monistat 7 Vaginal Suppositories; Monistat Dual- PAK; Monistat IV; Monistat-3 Combination Pack; Monistat-Derm; Novo-Miconazole Vaginal Ovules; Vusion; Zimycan
PharmGKB Accession Id: PA450494

Description

An imidazole antifungal agent that is used topically and by intravenous infusion. PubChem (source: Drug Bank)

Indication

For topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by <i>Trichophyton rubrum</i>, <i>Trichophyton mentagrophytes</i>, and <i>Epidermophyton floccosum</i>, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor. (source: Drug Bank)

ATC Therapeutic Categories

  • A01AB:Antiinfectives and antiseptics for local oral treatment
  • A07AC:Imidazole derivatives
  • D01AC:Imidazole and triazole derivatives
  • G01AF:Imidazole derivatives
  • J02AB:Imidazole derivatives
  • S02AA:Antiinfectives

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

Miconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Miconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis. (source: Drug Bank)

Pharmacology

Miconazole is an anti-fungal medication related to fluconazole (Diflucan), ketoconazole (Nizoral), itraconazole (Sporanox), and clotrimazole (Lotrimin, Mycelex). It is used either on the skin or in the vagina for fungal infections. Miconazole was approved by the FDA in 1974. Miconazole prevents fungal organisms from producing vital substances required for growth and function. This medication is effective only for infections caused by fungal organisms. It will not work for bacterial or viral infections. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Toxicity

Oral, mouse: LD<sub>50</sub> = 3800 mg/kg; Oral, rat: LD<sub>50</sub> = 3 gm/kg. Ingestion of the amounts of the components contained in a tube of cream are unlikely to produce overdosage and toxic effects. (source: Drug Bank)

Isomeric SMILES Code:

c1cc(c(cc1Cl)Cl)COC(Cn2ccnc2)c3ccc(cc3Cl)Cl (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
ABCC2
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Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2B6
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Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2C9
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No phenotype data Genotype Data Available Literature annotations available Not annotated
CYP2E1
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Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
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No phenotype data Genotype Data Available Literature annotations available Not annotated
GSTA1
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No phenotype data Genotype Data Available Literature annotations available Not annotated
GSTA2
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Phenotype data available Genotype Data Available Literature annotations available Has annotations
NR1I2
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No phenotype data Genotype Data Available Literature annotations available Not annotated
NR1I3
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Phenotype data available Genotype Data Available Literature annotations available Not annotated
NR3C1
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No phenotype data Genotype Data Available Literature annotations available Has annotations
SLCO1B1
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No phenotype data No genotype data Literature annotations available Not annotated
TAT
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Phenotype data available Genotype Data Available Literature annotations available Has annotations
UGT1A1
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A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
ATP2C1 Uncurated Annotation (source: Drug Bank)
CALM1 Uncurated Annotation (source: Drug Bank)
CALM3 Uncurated Annotation (source: Drug Bank)
CYP51A1 Uncurated Annotation (source: Drug Bank)

The following drugs are in curated knowledge about this drug.

  Drug Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
nateglinide
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No phenotype data No genotype data Literature annotations available Not annotated
zidovudine
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Publications

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

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation Vaginal miconazole increases the anticoagulant effect (source: Drug Bank)
anisindione Uncurated Annotation Vaginal miconazole increases the anticoagulant effect (source: Drug Bank)
dicumarol Uncurated Annotation Vaginal miconazole increases the anticoagulant effect (source: Drug Bank)
warfarin Uncurated Annotation Vaginal miconazole increases the anticoagulant effect (source: Drug Bank)

Non-Curated Information

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

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB01110
KEGG Compound ID:
C08070
KEGG Drug ID:
D00882
PubChem Compound ID:
4189
PubChem Substance ID:
602748
IUPHAR Ligand ID:
2449

Common Searches

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Non-Curated Publications

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

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