Drug/Small Molecule:
terbinafine

2D structure

Overview

Generic Names: Terbinafine HCl; Terbinafine hydrochloride; Ternbinafine HCl; terbinafine
Trade Names: Bramazil; Lamasil; Lamisil; Lamisil AT; Terbifoam; Terbina
PharmGKB Accession Id: PA451614

Description

Terbinafine hydrochloride (Lamisil) is a synthetic allylamine antifungal. It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. Like other allylamines, terbinafine inhibits ergosterol synthesis by inhibiting the fungal squalene epoxidase, an enzyme that is part of the fungal cell wall synthesis pathway. (source: Drug Bank)

Indication

For the treatment of interdigital tinea infections. (source: Drug Bank)

ATC Therapeutic Categories

  • D01AE:Other antifungals for topical use
  • D01BA:Antifungals for systemic use

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

Terbinafine is hypothesized to act by inhibiting squalene epoxidase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. (source: Drug Bank)

Pharmacology

Terbinafine is an allylamine antifungal agent and acts by inhibiting squalene epoxidase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. <i>in vitro</i>, mammalian squalene epoxidase is only inhibited at higher (4000 fold) concentrations than is needed for inhibition of the dermatophyte enzyme. Depending on the concentration of the drug and the fungal species test <i>in vitro</i>, Terbinafine may be fungicidal. However, the clinical significance of <i>in vitro</i> data is unknown. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (source: Drug Bank)

Protein Binding

>99% (source: Drug Bank)

Absorption

Readily absorbed from gastrointestinal tract. (source: Drug Bank)

Isomeric SMILES Code:

CC(C)(C)C#C/C=C/CN(C)Cc1cccc2c1cccc2 (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 Has annotations
CYP2D6
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  • PK
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  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
CYP3A
  •   
  • PD
  • PK
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Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
NR1I2
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  •   
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  • FA
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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
SQLE Uncurated Annotation (source: Drug Bank)

The following drugs are in curated knowledge about this drug.

  Drug Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
tamoxifen
  •   
  •   
  •   
  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
venlafaxine
  •   
  •   
  • PK
  •   
  •   
Publications

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

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation Terbinafine decreases the anticoagulant effect (source: Drug Bank)
atomoxetine Uncurated Annotation The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine (source: Drug Bank)
cyclosporine Uncurated Annotation Terbinafine decreases the effect of cyclosporine (source: Drug Bank)
desipramine Uncurated Annotation Terbinafine increases the effect and toxicity of the tricyclic (source: Drug Bank)
dextromethorphan Uncurated Annotation Terbinafine increases dextromethorphan levels (source: Drug Bank)
dicumarol Uncurated Annotation Terbinafine decreases the anticoagulant effect (source: Drug Bank)
imipramine Uncurated Annotation Terbinafine increases the effect and toxicity of the tricyclic (source: Drug Bank)
nortriptyline Uncurated Annotation Terbinafine increases the effect and toxicity of the tricyclic (source: Drug Bank)
rifampin Uncurated Annotation Rifampin decreases the effect of terbinafine (source: Drug Bank)
theophylline Uncurated Annotation Terbinafine increases the effect and toxicity of theophylline (source: Drug Bank)
warfarin Uncurated Annotation Terbinafine decreases the anticoagulant effect (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
Toxic liver disease
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  • PD
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  •   
  •   
Publications

Non-Curated Information

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

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00857
KEGG Compound ID:
C08079
KEGG Drug ID:
D02375
PubChem Compound ID:
5402
PubChem Substance ID:
7849434

Common Searches

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Non-Curated Publications

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

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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