Identification

Name
Terbinafine
Accession Number
DB00857
Description

Terbinafine hydrochloride (Lamisil) is a synthetic allylamine antifungal.9,10 It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues.1 Like other allylamines, terbinafine inhibits ergosterol synthesis by inhibiting the fungal squalene monooxygenase (also called squalene epoxidase), an enzyme that is part of the fungal cell wall synthesis pathway.1,2,10

Terbinafine hydrochloride was granted FDA approval on 30 December 1992.8

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 291.4299
Monoisotopic: 291.198699805
Chemical Formula
C21H25N
Synonyms
  • (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine
  • (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine
  • Terbinafina
  • Terbinafine
  • Terbinafinum
External IDs
  • SF 86-327
  • SF-86-327
  • TDT-067

Pharmacology

Indication

Terbinafine hydrochloride is indicated to treat fungal skin and nail infections caused by Trichophyton species, Microsporum canis, Epidermophyton floccosum,10 and Tinea species.9 Terbinafine hydrochloride also treats yeast infections of the skin caused by Candida species and Malassezia furfur.10

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Terbinafine is an allylamine antifungal that inhibits squalene epoxidase (also known as squalene monooxygenase) to prevent the formation of ergosterol and cause an accumulation of squalene, weakening the cell wall of fungal cells.1,2,10 Terbinafine distributes into tissues and has a long terminal elimination half life, so the duration of action is long.1 Overdose with terbinafine is rare, even above the therapeutic dose, so the therapeutic index is wide.9,10 Patients taking oral terbinafine should have liver function tests performed prior to treatment to reduce the risk of liver injury.9

Mechanism of action

Terbinafine inhibits the enzyme squalene monooxygenase (also called squalene epoxidase), preventing the conversion of squalene to 2,3-oxydosqualene, a step in the synthesis of ergosterol.1,2,10 This inhibition leads to decreased ergosterol, which would normally be incorporated into the cell wall, and accumulation of squalene.2,10

Generation of a large number of squalene containing vesicles in the cytoplasm may leach other lipids away from, and further weaken, the cell wall.2

TargetActionsOrganism
ASqualene monooxygenase
inhibitor
Yeast
NSqualene monooxygenase
inhibitor
Humans
Absorption

Oral terbinafine is >70% absorbed but only 40% bioavailable after first pass metabolism, reaching a Cmax of 1µg/mL with a Tmax of 2 hours an an AUC of 4.56µg*h/mL.9 Over the course of a week, 1% topical terbinafine's Cmax increases from 949-1049ng/cm2 and the AUC increases from 9694-13,492ng/cm2/h.4

Volume of distribution

A single 250mg oral dose of terbinafine has a volume of distribution at steady state of 947.5L or 16.6L/kg.1

Protein binding

Terbinafine is >99% bound to proteins in plasma,9 mostly to serum albumin,5 high and low density lipoproteins,1 and alpha-1-acid glycoprotein to a lesser extent.5

Metabolism

Terbinafine can be deaminated to 1-naphthaldehyde by CYP2C9, 2B6, 2C8, 1A2, 3A4, and 2C19.6 1-naphthaldehyde is then oxidized to 1-naphthoic acid or reduced to 1-naphthalenemethanol.6

Terbinafine can also be hydroxylated by CYP1A2, 2C9, 2C8, 2B6, and 2C19 to hydroxyterbinafine.6 Hydroxyterbinafine is then oxidized to carboxyterbinafine or N-demethylated by CYP3A4, 2B6, 1A2, 2C9, 2C8, and 2C19 to desmethylhydroxyterbinafine.6

Terbinafine can be N-demethylated to desmethylterbinafine.6 Desmethylterbinafine is then dihydroxylated to a desmethyldihydrodiol or hydroxylated to desmethylhydroxyterbinafine.6

Finally, terbinafine can be dihydroxylated to a dihydrodiol which is then N-demethylated to a desmethyldihydrodiol.6

Hover over products below to view reaction partners

Route of elimination

Terbinafine is approximately 80% eliminated in urine, while the remainder is eliminated in feces.1 The unmetabolized parent drug is not present in urine.7

Half-life

Oral terbinafine has an effective half life of approximately 36 hours.9 However, the terminal half life ranges from 200-400 hours as it distributes into skin and adipose tissue.9 1% topical terbinafine's half life increases over the first seven days from approximately 10-40 hours.4

Clearance

A single 250mg oral dose of terbinafine has a clearance of 76L/h or 1.11L/h/kg.1

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

The subcutaneous LD50 in rats and mice is >2g/kg.11 The TDLO for women is 210mg/kg/6W.11

Overdose data with terbinafine is rare, however symptoms are expected to be nausea, vomiting, abdominal pain, dizziness, rash, frequent urination, and headache.9 Treat overdose with activated charcoal as well as symptomatic and supportive therapy.10

Affected organisms
  • Fungi
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Terbinafine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Terbinafine can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Terbinafine.
AbirateroneThe serum concentration of Terbinafine can be increased when it is combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Terbinafine.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Terbinafine.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Terbinafine.
AcetaminophenThe metabolism of Terbinafine can be decreased when combined with Acetaminophen.
AcetohexamideThe metabolism of Terbinafine can be decreased when combined with Acetohexamide.
Acetyl sulfisoxazoleThe metabolism of Terbinafine can be decreased when combined with Acetyl sulfisoxazole.
Additional Data Available
  • Extended Description
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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
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  • Action
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Food Interactions
  • Limit caffeine intake. Terbinafine may reduce the metabolism of caffeine by approximately 19%, monitor for increased effects of caffeine.
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Terbinafine hydrochloride012C11ZU6G78628-80-5BWMISRWJRUSYEX-SZKNIZGXSA-N
Product Images
International/Other Brands
Lamasil
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act TerbinafineTabletOralTEVA Canada Limited2005-02-11Not applicableCanada flag
LamisilGranule187.5 mg/1OralNovartis Pharmaceuticals Corporation2007-09-282017-05-31US flag
LamisilSpray1 %TopicalNovartis1999-01-05Not applicableCanada flag
LamisilGranule125 mg/1OralNovartis Pharmaceuticals Corporation2007-09-282017-05-31US flag
LamisilTablet250 mg/1OralNovartis Pharmaceuticals Corporation1996-05-102018-10-31US flag
Lamisil Crm 1%CreamTopicalNovartis1993-12-31Not applicableCanada flag
Lamisil DermgelGelTopicalNovartisNot applicableNot applicableCanada flag
Lamisil Tab 250mgTabletOralNovartis1993-12-31Not applicableCanada flag
Q-terbinafineTabletOralQd Pharmaceuticals Ulc2012-02-032015-08-21Canada flag
TerbinafineTablet250 mgOralSanis Health Inc2010-07-26Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-terbinafineTabletOralApotex Corporation2000-05-16Not applicableCanada flag
Auro-terbinafineTabletOralAuro Pharma Inc2011-05-30Not applicableCanada flag
Auro-terbinafineTabletOralAuro Pharma IncNot applicableNot applicableCanada flag
Dom-terbinafineTabletOralDominion Pharmacal2011-03-03Not applicableCanada flag
Jamp-terbinafineTabletOralJamp Pharma Corporation2010-10-24Not applicableCanada flag
Mylan-terbinafineTabletOralMylan Pharmaceuticals2000-11-202017-01-09Canada flag
Nu-terbinafineTabletOralNu Pharm Inc2004-07-242012-09-04Canada flag
PHL-terbinafineTabletOralPharmel Inc2007-10-202016-10-25Canada flag
PMS-terbinafineTabletOralPharmascience Inc2000-02-142019-10-24Canada flag
PMS-terbinafineTabletOralPharmascience Inc2009-06-19Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AntifungalCream1 g/100gTopicalMeijer Distribution2007-07-02Not applicableUS flag
Antifungal FootCream1 g/100gTopicalAmerican Sales Company2007-07-02Not applicableUS flag
Athletes FootCream1 g/100gTopicalH E B2007-07-02Not applicableUS flag
Athletes FootCream1 g/100gTopicalTarget Corporation.2007-07-02Not applicableUS flag
Athletes FootCream1 g/100gTopicalPublix Supermarkets, Inc.2007-07-02Not applicableUS flag
Athletes FootCream1 g/100gTopicalChain Drug Marketing Association2007-07-02Not applicableUS flag
Athletes FootCream1 g/100gTopicalRite Aid Corporation2007-07-02Not applicableUS flag
Athletes FootCream10 mg/1gTopicalGlaxoSmithKline Consumer Healthcare Holdings (US) LLC2009-08-312014-09-30US flag
Athletes FootCream1 g/100gTopicalSupervalu2007-07-02Not applicableUS flag
Athletes FootCream1 g/100gTopicalTopco Associates LLC2007-07-02Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ciclopirox 8% / Fluconazole 1% / Terbinafine HCl 1%Terbinafine (1 g/100g) + Ciclopirox (8 g/100g) + Fluconazole (1 g/100g)SolutionTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag
Fluconazole 4% / Ibuprofen 2% / Itraconazole 1% / Terbinafine HCl 4%Terbinafine (4 g/100g) + Fluconazole (4 g/100g) + Ibuprofen (2 g/100g) + Itraconazole (1 g/100g)SolutionTopicalSincerus Florida, LLC2019-05-01Not applicableUS flag
Onycho-MedTerbinafine hydrochloride (250 mg/250mg) + Miconazole nitrate (200 mg/10mL)KitTopicalMedhart Pharmaceuticals, Inc.2019-04-16Not applicableUS flag
Terbinafine HCl 5%Terbinafine hydrochloride (5 g/100g)SolutionTopicalSincerus Florida, LLC2019-05-21Not applicableUS flag
Terbinafine HCl Chlortimazole and TolnaftateTerbinafine hydrochloride (1 g/100mL) + Clotrimazole (1 g/100mL) + Tolnaftate (1 g/100mL)SolutionTopicalDr Marc's Manufacturing And Sales2018-01-302018-04-17US flag
Terbinafine HCl CiclopiroxTerbinafine hydrochloride (4 g/100mL) + Ciclopirox (4 g/100mL)SolutionTopicalDr Marc's Manufacturing And Sales2018-01-302018-04-17US flag

Categories

ATC Codes
D01AE15 — TerbinafineD01BA02 — Terbinafine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
Aralkylamines / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Aralkylamine / Aromatic homopolycyclic compound / Hydrocarbon derivative / Naphthalene / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Tertiary aliphatic amine / Tertiary amine
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
allylamine antifungal drug, tertiary amine, naphthalenes, acetylenic compound, enyne (CHEBI:9448)

Chemical Identifiers

UNII
G7RIW8S0XP
CAS number
91161-71-6
InChI Key
DOMXUEMWDBAQBQ-WEVVVXLNSA-N
InChI
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+
IUPAC Name
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)[(naphthalen-1-yl)methyl]amine
SMILES
CN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12

References

Synthesis Reference

Graziano Castaldi, "Process for the preparation of terbinafine." U.S. Patent US20020123651, issued September 05, 2002.

US20020123651
General References
  1. Darkes MJ, Scott LJ, Goa KL: Terbinafine: a review of its use in onychomycosis in adults. Am J Clin Dermatol. 2003;4(1):39-65. [PubMed:12477372]
  2. Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7. [PubMed:1543672]
  3. Meletiadis J, Chanock S, Walsh TJ: Human pharmacogenomic variations and their implications for antifungal efficacy. Clin Microbiol Rev. 2006 Oct;19(4):763-87. doi: 10.1128/CMR.00059-05. [PubMed:17041143]
  4. Hill S, Thomas R, Smith SG, Finlay AY: An investigation of the pharmacokinetics of topical terbinafine (Lamisil) 1% cream. Br J Dermatol. 1992 Oct;127(4):396-400. doi: 10.1111/j.1365-2133.1992.tb00461.x. [PubMed:1419761]
  5. Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [PubMed:1287164]
  6. Vickers AE, Sinclair JR, Zollinger M, Heitz F, Glanzel U, Johanson L, Fischer V: Multiple cytochrome P-450s involved in the metabolism of terbinafine suggest a limited potential for drug-drug interactions. Drug Metab Dispos. 1999 Sep;27(9):1029-38. [PubMed:10460803]
  7. Jensen JC: Clinical pharmacokinetics of terbinafine (Lamisil). Clin Exp Dermatol. 1989 Mar;14(2):110-3. doi: 10.1111/j.1365-2230.1989.tb00904.x. [PubMed:2689012]
  8. FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Topical Cream (Discontinued) [Link]
  9. FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
  10. Health Canada Approved Drug Products: Lamisil Terbinafine Oral Tablets, Topical Cream, and Topical Spray [Link]
  11. Cayman Chemicals: Terbinafine MSDS [Link]
Human Metabolome Database
HMDB0014995
KEGG Drug
D02375
KEGG Compound
C08079
PubChem Compound
1549008
PubChem Substance
46508519
ChemSpider
1266005
BindingDB
50018518
RxNav
37801
ChEBI
9448
ChEMBL
CHEMBL822
ZINC
ZINC000001530981
Therapeutic Targets Database
DAP000753
PharmGKB
PA451614
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Terbinafine
AHFS Codes
  • 08:14.04 — Allylamines
  • 84:04.08.04 — Allylamines
FDA label
Download (137 KB)
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentOnychomycosis1
3CompletedNot AvailableDistal Subungual Onychomycosis1
3CompletedTreatmentDistal Subungual Onychomycosis1
3CompletedTreatmentOnychomycosis3
3CompletedTreatmentTinea Capitis2
3CompletedTreatmentTinea Pedis1
3Unknown StatusTreatmentAntifungal Drugs in Onychomycosis1
3Unknown StatusTreatmentOnychomycosis1
3WithdrawnTreatmentOnychomycosis of Toenail1
2CompletedNot AvailableDistal Subungual Onychomycosis1

Pharmacoeconomics

Manufacturers
  • Novartis consumer health inc
  • Novartis pharmaceuticals corp
  • Taro pharmaceuticals usa inc
  • Apotex corp
  • Aurobindo pharma ltd
  • Breckenridge pharmaceutical inc
  • Dr reddys laboratories inc
  • Gedeon richter usa inc
  • Genpharm inc
  • Glenmark generics ltd
  • Harris pharmaceutical inc
  • Invagen pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Orchid healthcare
  • Roxane laboratories inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Wockhardt ltd
Packagers
  • Actavis Group
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Blu Pharmaceuticals LLC
  • Bryant Ranch Prepack
  • Camber Pharmaceuticals Inc.
  • Cipla Ltd.
  • CVS Pharmacy
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Glenmark Generics Ltd.
  • Harris Pharmaceutical Inc.
  • InvaGen Pharmaceuticals Inc.
  • JSJ Pharmaceuticals Inc.
  • Kaiser Foundation Hospital
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Northstar Rx LLC
  • Novartis AG
  • Orchid Healthcare
  • Patheon Inc.
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sandoz
  • Southwood Pharmaceuticals
  • Sunmark
  • Target Corp.
  • Teva Pharmaceutical Industries Ltd.
  • The Jay Group Inc.
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
CreamTopical10 mg/1g
SprayTopical1 %
CreamTopical1 g
SolutionTopical1 g
GelTopical1 mg
SolutionTopical
CreamTopical1 g/100g
GelTopical1 g
CreamTopical1 %
GelTopical1 %
GranuleOral125 mg/1
GranuleOral187.5 mg/1
LiquidTopical1 g/100g
SprayTopical1.25 mL/125mL
TabletOral250 MG
Aerosol, sprayTopical0.84 g/125mL
SprayTopical1 mL/100mL
SprayTopical1 g/100mL
GelTopical10 mg/1g
LiquidTopical0.84 g/125mL
CreamTopical
GelTopical
SolutionTopical1 %
TabletOral
CreamTopical1 mg/g
CreamTopical10 MG/G
TabletOral500 mg
LotionTopical1 %
KitTopical
PowderTopical1 g
SprayTopical
OintmentTopical1 %
SprayTopical10 mg/g
SolutionTopical10 mg/g
GelTopical1000 mg
TabletOral125 MG
Tablet, coatedOral250 mg
AerosolTopical1 g
SolutionTopical5 g/100g
TabletOral250 1/1
TabletOral250 mg/1
Prices
Unit descriptionCostUnit
LamISIL 14 187.5 mg Packets Packet202.16USD packet
LamISIL 1% Solution 30ml Bottle88.18USD bottle
Terbinafine hcl powder42.84USD g
Terbinafine HCl 1% Cream 24 gm Tube17.99USD tube
Lamisil 250 mg tablet14.22USD tablet
Terbinafine hcl 250 mg tablet13.19USD tablet
Lamisil 250 mg Tablet4.79USD tablet
Apo-Terbinafine 250 mg Tablet2.64USD tablet
Co Terbinafine 250 mg Tablet2.64USD tablet
Mylan-Terbinafine 250 mg Tablet2.64USD tablet
Novo-Terbinafine 250 mg Tablet2.64USD tablet
Pms-Terbinafine 250 mg Tablet2.64USD tablet
Sandoz Terbinafine 250 mg Tablet2.64USD tablet
Lamisil 1% cream2.13USD g
Lamisil 1 % Solution0.58USD g
Lamisil 1 % Cream0.57USD g
Sm athlete's 1% foot cream0.53USD g
Lamisil at 1% cream0.51USD g
CVS Pharmacy jock itch 1% cream0.49USD g
CVS Pharmacy athlete's foot 1% cream0.4USD g
Athlete's 1% foot cream0.27USD g
Lamisil af defense crm to powd0.2USD g
Lamisil antifungal 1% spray0.07USD ml
Lamisil af defense 1% powder0.05USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5681849No1997-10-282015-04-28US flag
US5856355No1999-01-052012-05-18US flag
CA2062341No2004-05-112012-03-05Canada flag
CA2068957No2002-12-172012-05-19Canada flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)205Health Canada
boiling point (°C)417.9ChemSpider
water solubility0.63%Health Canada
pKa7.10Health Canada
Predicted Properties
PropertyValueSource
Water Solubility0.000738 mg/mLALOGPS
logP5.51ALOGPS
logP5.53ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.08 m3·mol-1ChemAxon
Polarizability35.84 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9876
Blood Brain Barrier+0.9381
Caco-2 permeable+0.7436
P-glycoprotein substrateSubstrate0.6026
P-glycoprotein inhibitor INon-inhibitor0.7495
P-glycoprotein inhibitor IIInhibitor0.8205
Renal organic cation transporterNon-inhibitor0.581
CYP450 2C9 substrateNon-substrate0.7806
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6461
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 inhibitorNon-inhibitor0.8951
CYP450 2D6 inhibitorInhibitor0.6772
CYP450 2C19 inhibitorNon-inhibitor0.6194
CYP450 3A4 inhibitorNon-inhibitor0.6314
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5884
Ames testNon AMES toxic0.8736
CarcinogenicityCarcinogens 0.5109
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8932 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8785
hERG inhibition (predictor II)Non-inhibitor0.5566
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-3940000000-70d0c46dfa6b0976b000
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-1920000000-a7ec8e83df0d61d1f6b5

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
Yes
Actions
Inhibitor
General Function
Squalene monooxygenase activity
Specific Function
Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name
ERG1
Uniprot ID
Q92206
Uniprot Name
Squalene monooxygenase
Molecular Weight
55297.635 Da
References
  1. Darkes MJ, Scott LJ, Goa KL: Terbinafine: a review of its use in onychomycosis in adults. Am J Clin Dermatol. 2003;4(1):39-65. [PubMed:12477372]
  2. Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7. [PubMed:1543672]
  3. Health Canada Approved Drug Products: Lamisil Terbinafine Oral Tablets, Topical Cream, and Topical Spray [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Squalene monooxygenase activity
Specific Function
Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name
SQLE
Uniprot ID
Q14534
Uniprot Name
Squalene monooxygenase
Molecular Weight
63922.505 Da
References
  1. Sander CS, Hipler UC, Wollina U, Elsner P: Inhibitory effect of terbinafine on reactive oxygen species (ROS) generation by Candida albicans. Mycoses. 2002 Jun;45(5-6):152-5. [PubMed:12100530]
  2. Wentzinger LF, Bach TJ, Hartmann MA: Inhibition of squalene synthase and squalene epoxidase in tobacco cells triggers an up-regulation of 3-hydroxy-3-methylglutaryl coenzyme a reductase. Plant Physiol. 2002 Sep;130(1):334-46. [PubMed:12226513]
  3. Darkes MJ, Scott LJ, Goa KL: Terbinafine: a review of its use in onychomycosis in adults. Am J Clin Dermatol. 2003;4(1):39-65. [PubMed:12477372]
  4. Klobucnikova V, Kohut P, Leber R, Fuchsbichler S, Schweighofer N, Turnowsky F, Hapala I: Terbinafine resistance in a pleiotropic yeast mutant is caused by a single point mutation in the ERG1 gene. Biochem Biophys Res Commun. 2003 Sep 26;309(3):666-71. [PubMed:12963042]
  5. Leber R, Fuchsbichler S, Klobucnikova V, Schweighofer N, Pitters E, Wohlfarter K, Lederer M, Landl K, Ruckenstuhl C, Hapala I, Turnowsky F: Molecular mechanism of terbinafine resistance in Saccharomyces cerevisiae. Antimicrob Agents Chemother. 2003 Dec;47(12):3890-900. [PubMed:14638499]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7. [PubMed:1543672]
  8. Krishnan-Natesan S: Terbinafine: a pharmacological and clinical review. Expert Opin Pharmacother. 2009 Nov;10(16):2723-33. doi: 10.1517/14656560903307462. [PubMed:19874252]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  3. Vickers AE, Sinclair JR, Zollinger M, Heitz F, Glanzel U, Johanson L, Fischer V: Multiple cytochrome P-450s involved in the metabolism of terbinafine suggest a limited potential for drug-drug interactions. Drug Metab Dispos. 1999 Sep;27(9):1029-38. [PubMed:10460803]
  4. FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Vickers AE, Sinclair JR, Zollinger M, Heitz F, Glanzel U, Johanson L, Fischer V: Multiple cytochrome P-450s involved in the metabolism of terbinafine suggest a limited potential for drug-drug interactions. Drug Metab Dispos. 1999 Sep;27(9):1029-38. [PubMed:10460803]
  2. FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Vickers AE, Sinclair JR, Zollinger M, Heitz F, Glanzel U, Johanson L, Fischer V: Multiple cytochrome P-450s involved in the metabolism of terbinafine suggest a limited potential for drug-drug interactions. Drug Metab Dispos. 1999 Sep;27(9):1029-38. [PubMed:10460803]
  3. FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Vickers AE, Sinclair JR, Zollinger M, Heitz F, Glanzel U, Johanson L, Fischer V: Multiple cytochrome P-450s involved in the metabolism of terbinafine suggest a limited potential for drug-drug interactions. Drug Metab Dispos. 1999 Sep;27(9):1029-38. [PubMed:10460803]
  3. FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Vickers AE, Sinclair JR, Zollinger M, Heitz F, Glanzel U, Johanson L, Fischer V: Multiple cytochrome P-450s involved in the metabolism of terbinafine suggest a limited potential for drug-drug interactions. Drug Metab Dispos. 1999 Sep;27(9):1029-38. [PubMed:10460803]
  2. FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Abdel-Rahman SM, Marcucci K, Boge T, Gotschall RR, Kearns GL, Leeder JS: Potent inhibition of cytochrome P-450 2D6-mediated dextromethorphan O-demethylation by terbinafine. Drug Metab Dispos. 1999 Jul;27(7):770-5. [PubMed:10383919]
  2. Madani S, Barilla D, Cramer J, Wang Y, Paul C: Effect of terbinafine on the pharmacokinetics and pharmacodynamics of desipramine in healthy volunteers identified as cytochrome P450 2D6 (CYP2D6) extensive metabolizers. J Clin Pharmacol. 2002 Nov;42(11):1211-8. [PubMed:12412819]
  3. Debruyne D, Coquerel A: Pharmacokinetics of antifungal agents in onychomycoses. Clin Pharmacokinet. 2001;40(6):441-72. [PubMed:11475469]
  4. Abdel-Rahman SM, Gotschall RR, Kauffman RE, Leeder JS, Kearns GL: Investigation of terbinafine as a CYP2D6 inhibitor in vivo. Clin Pharmacol Ther. 1999 May;65(5):465-72. [PubMed:10340911]
  5. Flockhart Table of Drug Interactions [Link]
  6. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  7. FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Schafer-Korting M, Korting HC, Rittler W, Obermuller W: Influence of serum protein binding on the in vitro activity of anti-fungal agents. Infection. 1995 Sep-Oct;23(5):292-7. doi: 10.1007/bf01716289. [PubMed:8557388]
  2. Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [PubMed:1287164]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [PubMed:1287164]

Transporters

Kind
Protein
Organism
Trichophyton interdigitale (strain MR816)
Pharmacological action
Unknown
Actions
Substrate
General Function
Pleiotropic ABC efflux transporter that may be involved in the modulation susceptibility to a wide range of unrelated cytotoxic compounds, including terbinafine, 4-nitroquinoline N-oxide, and ethidium bromide (PubMed:16849730). May play a role in pathogenicity (PubMed:19141731).
Specific Function
Atp binding
Gene Name
MDR2
Uniprot ID
A0A059JJ46
Uniprot Name
ABC multidrug transporter MDR2
Molecular Weight
145278.17 Da
References
  1. Fachin AL, Ferreira-Nozawa MS, Maccheroni W Jr, Martinez-Rossi NM: Role of the ABC transporter TruMDR2 in terbinafine, 4-nitroquinoline N-oxide and ethidium bromide susceptibility in Trichophyton rubrum. J Med Microbiol. 2006 Aug;55(Pt 8):1093-9. doi: 10.1099/jmm.0.46522-0. [PubMed:16849730]

Drug created on June 13, 2005 07:24 / Updated on November 30, 2020 13:38

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