Chemical: Drug
terbinafine

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last updated 09/01/2016

1. FDA Label for terbinafine and CYP2D6

Informative PGx

Former FDA Biomarker

This label used to be included on the FDA biomarker list and has since been removed. The PharmGKB curation staff monitors the FDA biomarker list on a regular basis and notes removals. There is no official list of removals supplied by the FDA.

Full label available at DailyMed

Genes and/or phenotypes found in this label

  • Mycoses
    • Indications & usage section
    • source: U.S. Food and Drug Administration
  • Toxic liver disease
    • Warnings section
    • source: PHONT
  • CYP2D6
    • metabolism/PK, Drug interactions section
    • source: U.S. Food and Drug Administration

PharmGKB contains no Clinical Variants that meet the highest level of criteria.

Disclaimer: The PharmGKB's clinical annotations reflect expert consensus based on clinical evidence and peer-reviewed literature available at the time they are written and are intended only to assist clinicians in decision-making and to identify questions for further research. New evidence may have emerged since the time an annotation was submitted to the PharmGKB. The annotations are limited in scope and are not applicable to interventions or diseases that are not specifically identified.

The annotations do not account for individual variations among patients, and cannot be considered inclusive of all proper methods of care or exclusive of other treatments. It remains the responsibility of the health-care provider to determine the best course of treatment for a patient. Adherence to any guideline is voluntary, with the ultimate determination regarding its application to be made solely by the clinician and the patient. PharmGKB assumes no responsibility for any injury or damage to persons or property arising out of or related to any use of the PharmGKB clinical annotations, or for any errors or omissions.

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Overview

Generic Names
  • Terbinafine HCl
  • Terbinafine hydrochloride
  • Ternbinafine HCl
  • terbinafine
Trade Names
  • Bramazil
  • Lamasil
  • Lamisil
  • Lamisil AT
  • Lamisil Oral
  • Terbifoam
  • Terbina
Brand Mixture Names

PharmGKB Accession Id

PA451614

Type(s):

Drug

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 monooxygenase (squalene 2,3-epoxidase), an enzyme that is part of the fungal cell wall synthesis pathway.

Source: Drug Bank

Indication

For the treatment of dermatophyte infections of the toenail or fingernail caused by susceptible fungi. Also for the treatment of tinea capitis (scalp ringworm) and tinea corporis (body ringworm) or tinea cruris (jock itch).

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

Terbinafine is hypothesized to act by inhibiting squalene monooxygenase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. This inhibition also results in an accumulation of squalene, which is a substrate catalyzed to 2,3-oxydo squalene by squalene monooxygenase. The resultant high concentration of squalene and decreased amount of ergosterol are both thought to contribute to terbinafine's antifungal activity.

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. In vitro, mammalian squalene monooxygenase (squalene 2,3-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.

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

Half-Life

36 hours

Source: Drug Bank

Route of Elimination

Prior to excretion, terbinafine is extensively metabolized.

Source: Drug Bank

Chemical Properties

Chemical Formula

C21H25N

Source: Drug Bank

Isomeric SMILES

CC(C)(C)C#C/C=C/CN(C)Cc1cccc2c1cccc2

Source: OpenEye

Canonical SMILES

CN(CC=CC#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12

Source: Drug Bank

Average Molecular Weight

291.4299

Source: Drug Bank

Monoisotopic Molecular Weight

291.198699805

Source: Drug Bank

SMILES

CN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12

Source: Drug Bank

InChI String

InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

Curated Information ?

Drug Targets

Gene Description
SQLE (source: Drug Bank )

Drug Interactions

Interaction Description
aminophylline - terbinafine Terbinafine increases the effect and toxicity of theophylline (source: Drug Bank )
atomoxetine - terbinafine The CYP2D6 inhibitor could increase the effect and toxicity of atomoxetine (source: Drug Bank )
cyclosporine - terbinafine Terbinafine decreases the effect of cyclosporine (source: Drug Bank )
cyclosporine - terbinafine Terbinafine decreases the effect of cyclosporine (source: Drug Bank )
desipramine - terbinafine Terbinafine increases the effect and toxicity of the tricyclic (source: Drug Bank )
desipramine - terbinafine Terbinafine increases the effect and toxicity of the tricyclic antidepressant, desipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of desipramine if terbinafine is initiated, discontinued or dose changed. (source: Drug Bank )
dextromethorphan - terbinafine Terbinafine increases dextromethorphan levels (source: Drug Bank )
dextromethorphan - terbinafine Terbinafine increases dextromethorphan levels (source: Drug Bank )
imipramine - terbinafine Terbinafine increases the effect and toxicity of the tricyclic (source: Drug Bank )
imipramine - terbinafine Terbinafine increases the effect and toxicity of the tricyclic antidepressant, imipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of imipramine if terbinafine is initiated, discontinued or dose changed. (source: Drug Bank )
nortriptyline - terbinafine Terbinafine increases the effect and toxicity of the tricyclic (source: Drug Bank )
nortriptyline - terbinafine Terbinafine increases the effect and toxicity of the tricyclic antidepressant, nortriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nortriptyline if terbinafine is initiated, discontinued or dose changed. (source: Drug Bank )
oxtriphylline - terbinafine Terbinafine increases the effect and toxicity of theophylline (source: Drug Bank )
rifampin - terbinafine Rifampin decreases the effect of terbinafine (source: Drug Bank )
rifampin - terbinafine Rifampin decreases the effect of terbinafine (source: Drug Bank )
tamoxifen - terbinafine Terbinafine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided. (source: Drug Bank )
tamoxifen - terbinafine Terbinafine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Concomitant therapy should be avoided. (source: Drug Bank )
tamsulosin - terbinafine Terbinafine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Terbinafine is initiated, discontinued, or dose changed. (source: Drug Bank )
tamsulosin - terbinafine Terbinafine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Terbinafine is initiated, discontinued, or dose changed. (source: Drug Bank )
theophylline - terbinafine Terbinafine increases the effect and toxicity of theophylline (source: Drug Bank )
theophylline - terbinafine Terbinafine increases the effect and toxicity of theophylline (source: Drug Bank )
tolterodine - terbinafine Terbinafine may decrease the metabolism and clearance of Tolterodine. Monitor for adverse/toxic effects of Tolterodine. (source: Drug Bank )
tolterodine - terbinafine Terbinafine may decrease the metabolism and clearance of Tolterodine. Monitor for adverse/toxic effects of Tolterodine. (source: Drug Bank )
tramadol - terbinafine Terbinafine may decrease the effect of Tramadol by decreasing active metabolite production. (source: Drug Bank )
trimipramine - terbinafine Terbinafine may decrease the metabolism and clearance of Trimipramine. Monitor for changes in Trimipramine efficacy and toxicity if Terbinafine is initiated, discontinued or dose changed. Alteration in Trimipramine dose may be required. (source: Drug Bank )
venlafaxine - terbinafine Terbinafine, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Terbinafine is initiated, discontinued, or dose changed. (source: Drug Bank )
zuclopenthixol - terbinafine Terbinafine, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if terbinafine is initiated, discontinued or dose changed. (source: Drug Bank )

Curated Information ?

Relationships from National Drug File - Reference Terminology (NDF-RT)

May Treat
Contraindicated With

Publications related to terbinafine: 12

No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
T Cell-Mediated Hypersensitivity Reactions to Drugs. Annual review of medicine. 2014. Pavlos Rebecca, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Challenges in pharmacogenetics. European journal of clinical pharmacology. 2013. Cascorbi Ingolf, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Systematic review of pharmacoeconomic studies of pharmacogenomic tests. Pharmacogenomics. 2010. Beaulieu Mathieu, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Coprescription of tamoxifen and medications that inhibit CYP2D6. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2010. Sideras Kostandinos, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
ADME pharmacogenetics: current practices and future outlook. Expert opinion on drug metabolism & toxicology. 2009. Grossman Iris. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Machine learning methods and docking for predicting human pregnane X receptor activation. Chemical research in toxicology. 2008. Khandelwal Akash, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Effect of terbinafine and voriconazole on the pharmacokinetics of the antidepressant venlafaxine. Clinical pharmacology and therapeutics. 2008. Hynninen V-V, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Terbinafine increases the plasma concentration of paroxetine after a single oral administration of paroxetine in healthy subjects. European journal of clinical pharmacology. 2007. Yasui-Furukori Norio, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Voriconazole, but not terbinafine, markedly reduces alfentanil clearance and prolongs its half-life. Clinical pharmacology and therapeutics. 2006. Saari Teijo I, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Prolonged pharmacokinetic drug interaction between terbinafine and amitriptyline. Therapeutic drug monitoring. 2005. Castberg Ingrid, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Idiosyncratic drug hepatotoxicity. Nature reviews. Drug discovery. 2005. Kaplowitz Neil. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Investigation of terbinafine as a CYP2D6 inhibitor in vivo. Clinical pharmacology and therapeutics. 1999. Abdel-Rahman S M, et al. PubMed

LinkOuts

Web Resource:
Wikipedia
National Drug Code Directory:
0378-5710-93
DrugBank:
DB00857
KEGG Compound:
C08079
KEGG Drug:
D02375
PubChem Compound:
1549008
PubChem Substance:
46508519
7849434
Drugs Product Database (DPD):
2240346
ChemSpider:
5209
Therapeutic Targets Database:
DAP000753
FDA Drug Label at DailyMed:
8b6dab4d-5b80-4690-8d96-3438d69c7d1d

Clinical Trials

These are trials that mention terbinafine and are related to either pharmacogenetics or pharmacogenomics.

No trials loaded.

NURSA Datasets

provided by nursa.org

No NURSA datasets available.

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Sources for PharmGKB drug information: DrugBank, PubChem.