Overview
| Generic Names: | Terbinafine HCl; Terbinafine hydrochloride; Ternbinafine HCl; terbinafine |
|---|---|
| IUPAC Name: | N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine |
| 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.
Indication
For the treatment of interdigital tinea infections.
ATC Therapeutic Categories
- D01AE:Other antifungals for topical use
- D01BA:Antifungals for systemic use
Pharmacology and Interactions
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.
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. in vitro, 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 in vitro, Terbinafine may be fungicidal. However, the clinical significance of in vitro data is unknown.
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Hepatic
Protein Binding
>99%
Absorption
Readily absorbed from gastrointestinal tract.
Half Life
36 hours
Chemical Properties
Chemical Formula:
C21H25N
SMILES Code:
CC(C)(C)C#C/C=C/CN(C)Cc1cccc2c1cccc2
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
291.4299 / 291.1987
Curated Information
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
|---|---|---|---|
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CYP2D6 |
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Publications |
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CYP3A |
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Publications |
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NR1I2 |
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Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Metabolizing Enzymes
Drug Targets
Curated Information
The following drugs are in curated knowledge about this drug.
| Drug | Relationship | Evidence | |
|---|---|---|---|
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venlafaxine |
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Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| acenocoumarol | Terbinafine decreases the anticoagulant effect |
| aminophylline | Terbinafine increases the effect and toxicity of theophylline |
| anisindione | Terbinafine decreases the anticoagulant effect |
| atomoxetine | The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine |
| cyclosporine | Terbinafine decreases the effect of cyclosporine |
| desipramine | Terbinafine increases the effect and toxicity of the tricyclic |
| dextromethorphan | Terbinafine increases dextromethorphan levels |
| dicumarol | Terbinafine decreases the anticoagulant effect |
| dyphylline | Terbinafine increases the effect and toxicity of theophylline |
| imipramine | Terbinafine increases the effect and toxicity of the tricyclic |
| nortriptyline | Terbinafine increases the effect and toxicity of the tricyclic |
| oxtriphylline | Terbinafine increases the effect and toxicity of theophylline |
| rifampin | Rifampin decreases the effect of terbinafine |
| theophylline | Terbinafine increases the effect and toxicity of theophylline |
| warfarin | Terbinafine decreases the anticoagulant effect |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
|---|---|---|---|
|
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Toxic liver disease |
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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
Common Searches
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.