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Identification
NameTerbinafine
Accession NumberDB00857  (APRD00508)
TypeSmall Molecule
GroupsApproved, Investigational, Vet Approved
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.

Structure
Thumb
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
Terbinafinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Terbinafinetablet250 mgoralActavis Pharma Company2005-02-11Not applicableCanada
Auro-terbinafinetablet250 mgoralAuro Pharma Inc2011-05-30Not applicableCanada
Auro-terbinafinetablet125 mgoralAuro Pharma IncNot applicableNot applicableCanada
Dom-terbinafinetablet250 mgoralDominion Pharmacal2011-03-03Not applicableCanada
Jamp-terbinafinetablet250 mgoralJamp Pharma Corporation2010-10-24Not applicableCanada
Lamisiltablet250 mg/1oralNovartis Pharmaceuticals Corporation1996-05-10Not applicableUs
Lamisilgranule187.5 mg/1oralNovartis Pharmaceuticals Corporation2007-09-28Not applicableUs
Lamisilgranule125 mg/1oralNovartis Pharmaceuticals Corporation2007-09-28Not applicableUs
Lamisil Crm 1%cream1 %topicalNovartis Pharmaceuticals Canada Inc1993-12-31Not applicableCanada
Lamisil Dermgelgel10 mgtopicalNovartis Pharmaceuticals Canada IncNot applicableNot applicableCanada
Lamisil Sprayspray10 mgtopicalNovartis Pharmaceuticals Canada Inc1999-01-05Not applicableCanada
Lamisil Tab 250mgtablet250 mgoralNovartis Pharmaceuticals Canada Inc1993-12-31Not applicableCanada
Mylan-terbinafinetablet250 mgoralMylan Pharmaceuticals Ulc2000-11-20Not applicableCanada
Nu-terbinafinetablet250 mgoralNu Pharm Inc2004-07-242012-09-04Canada
PHL-terbinafinetablet250 mgoralPharmel Inc2007-10-20Not applicableCanada
PMS-terbinafinetablet250 mgoralPharmascience Inc2000-02-14Not applicableCanada
PMS-terbinafinetablet250 mgoralPharmascience Inc2009-06-19Not applicableCanada
PMS-terbinafine Creamcream1 %topicalPharmascience IncNot applicableNot applicableCanada
PMS-terbinafine Sprayspray1 %topicalPharmascience IncNot applicableNot applicableCanada
Q-terbinafinetablet250 mgoralQd Pharmaceuticals Ulc2012-02-032015-08-21Canada
Riva-terbinafinetablet250 mgoralLaboratoire Riva Inc2005-02-10Not applicableCanada
Sandoz-terbinafinetablet250 mgoralSandoz Canada Incorporated2005-12-07Not applicableCanada
Terbinafinetablet250 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Terbinafinetablet250 mgoralSanis Health Inc2010-07-26Not applicableCanada
Terbinafinetablet250 mgoralSivem Pharmaceuticals Ulc2012-06-10Not applicableCanada
Terbinafinetablet250 mgoralPrempharm Inc2003-09-032005-08-05Canada
Terbinafinetablet250 mgoralPro Doc Limitee2008-03-07Not applicableCanada
Teva-terbinafinetablet250 mgoralTeva Canada Limited2001-02-28Not applicableCanada
Teva-terbinafinetablet125 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-terbinafinetablet250 mgoralApotex Inc2000-05-16Not applicableCanada
Terbinafinetablet250 mg/1oralExelan Pharmaceuticals Inc.2012-04-25Not applicableUs
Terbinafinetablet250 mg/1oralHarris Pharmaceutical, Inc.2007-07-30Not applicableUs
Terbinafinetablet250 mg/1oralAurobindo Pharma Limited2007-07-02Not applicableUs
Terbinafine Hydochloridetablet250 mg/1oralPhysicians Total Care, Inc.2007-07-12Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralWockhardt USA, LLC2008-01-04Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralbryant ranch prepack2011-01-01Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralNorthstar Rx LLC2009-09-15Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralPreferred Pharmaceuticals, Inc2011-06-29Not applicableUs
Terbinafine Hydrochloridetablet250 1/1oralProficient Rx LP2011-01-01Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralREMEDYREPACK INC.2013-02-112016-04-05Us
Terbinafine Hydrochloridetablet250 mg/1oralDIRECT RX2015-01-01Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralBreckenridge Pharmaceutical, Inc.2010-12-27Not applicableUs
Terbinafine Hydrochloridetablet250 1/1oralCarilion Materials Management2011-01-01Not applicableUs
Terbinafine Hydrochloridecream1 g/100gtopicalREMEDYREPACK INC.2015-03-12Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralPd Rx Pharmaceuticals, Inc.2014-08-13Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralAmerican Health Packaging2014-07-31Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralGolden State Medical Supply, Inc.2010-12-27Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralAv Kare, Inc.2011-10-20Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralWockhardt Limited2007-07-02Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-09-16Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralHarris Pharmaceutical, Inc.2014-08-13Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralPd Rx Pharmaceuticals, Inc.2011-06-29Not applicableUs
Terbinafine Hydrochloridetablet250 1/1oralCamber Pharmaceuticals, Inc.2011-01-01Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralWockhardt USA LLC.2007-07-02Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralDr.Reddys Laboratories Limited2007-07-02Not applicableUs
Terbinafine Hydrochloridetablet250 mg/1oralRebel Distributors Corp2007-07-02Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antifungalcream1 g/100gtopicalMeijer Distribution Inc2007-07-02Not applicableUs
Antifungal Footcream1 g/100gtopicalAmerican Sales Company2007-07-02Not applicableUs
Athletes Footcream1 g/100gtopicalMc Kesson2007-07-02Not applicableUs
Athletes Footcream1 g/100gtopicalTopco Associates LLC2007-07-02Not applicableUs
Athletes Footcream1 g/100gtopicalPublix Super Markets Inc.2007-07-02Not applicableUs
Athletes Footcream10 mg/gtopicalNovartis Cosnumer Health, Inc2009-08-31Not applicableUs
Athletes Footcream1 g/100gtopicalSafeway Inc.2007-07-02Not applicableUs
Athletes Footcream10 mg/gtopicalTarget Corporation2009-08-31Not applicableUs
Athletes Footcream1 g/100gtopicalTarget Corporation2007-07-02Not applicableUs
Athletes Footcream1 g/100gtopicalSupervalu Inc2007-07-02Not applicableUs
Athletes Footcream1 g/100gtopicalChain Drug Marketing Association, Inc.2007-07-02Not applicableUs
Athletes Footcream1 g/100gtopicalH E B2007-07-02Not applicableUs
Cvscream1 g/100gtopicalCVS Pharmacy2007-07-02Not applicableUs
Cvs Pharmacy Athletes Footcream1 g/100gtopicalCVS Pharmacy2007-07-02Not applicableUs
Equate Athletes Footcream1 g/100gtopicalWal Mart Stores Inc2007-07-02Not applicableUs
Good Neighbor Pharmacycream1 g/100gtopicalAmerisource Bergen2007-07-02Not applicableUs
Goodsense Terbinafine Hydrochloridecream1 g/100gtopicalGeiss, Destin & Dunn, Inc.2007-07-02Not applicableUs
Kaiser Permanente Terbinafine Hydrochloridecream1 g/100gtopicalKAISER FOUNDATION HOSPITALS2007-07-02Not applicableUs
Kroger Antifungalcream1 g/100gtopicalKroger Company2007-07-02Not applicableUs
Lamisilspray1.25 mL/125mLtopicalPhysicians Total Care, Inc.2010-04-13Not applicableUs
Lamisil Atcream10 mg/gtopicalNovartis Consumer Health, Inc.2005-08-10Not applicableUs
Lamisil Atcream1 g/100gtopicalGlaxo Smith Kline Consumer Healthcare Holdings (Us) Llc2007-07-02Not applicableUs
Lamisil Atcream10 mg/gtopicalNovartis Consumer Health, Inc.2005-08-10Not applicableUs
Lamisil Atspray1 mL/100mLtopicalNovartis Consumer Health, Inc.2000-05-01Not applicableUs
Lamisil At Antifungalgel10 mg/gtopicalNovartis Consumer Health, Inc.2010-01-01Not applicableUs
Lamisil At Continuous Sprayliquid1.25 mL/125mLtopicalNovartis Consumer Health, Inc.2009-07-23Not applicableUs
Lamisil At Continuous Sprayliquid1.25 mL/125mLtopicalNovartis Consumer Health, Inc.2009-07-23Not applicableUs
Lamisil At for Jock Itchcream1 g/100gtopicalNovartis Consumer Health, Inc.2007-07-02Not applicableUs
Lamisil At Jock Itchcream10 mg/gtopicalNovartis Consumer Health, Inc.2006-12-08Not applicableUs
Live Better Antifungalcream1 g/100gtopicalThe Great Atlantic & Pacific Tea Company2007-07-02Not applicableUs
Preferred Pluscream1 g/100gtopicalPreferred Plus (Kinray)2007-07-02Not applicableUs
Shopko Athletes Footcream1 g/100gtopicalShopko Stores Operating Co., LLC2007-07-02Not applicableUs
Shopritecream1 g/100gtopicalWakefern Food Corporation2007-07-02Not applicableUs
Silka Antifungalcream1 g/100gtopicalGenomma Lab Usa, Inc.2007-07-02Not applicableUs
Terbinafine Hydrochloridecream1 g/100gtopicalPhysicians Total Care, Inc.2009-02-24Not applicableUs
Terbinafine Hydrochloridecream1 g/100gtopicalPreferred Pharmaceuticals, Inc2012-04-05Not applicableUs
Terbinafine Hydrochloridecream1 g/100gtopicalTaro Pharmaceuticals U.S.A., Inc.2007-07-02Not applicableUs
Terbinafine Hydrochloridecream1 g/100gtopicalChain Drug Constortium2007-07-02Not applicableUs
Terbinafine Hydrochloridecream1 g/100gtopicalWalgreen Company2007-07-02Not applicableUs
Terbinafine Hydrochloridecream1 g/100gtopicalProficient Rx LP2007-07-02Not applicableUs
Terbinafine Hydrochloridecream1 g/100gtopicalCardinal Health2007-07-02Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
LamasilNot Available
TerbinexNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Terbinafine Hydrochloride
Thumb
  • InChI Key: BWMISRWJRUSYEX-SZKNIZGXSA-N
  • Monoisotopic Mass: 327.175377544
  • Average Mass: 327.891
DBSALT000470
Categories
UNIIG7RIW8S0XP
CAS number91161-71-6
WeightAverage: 291.4299
Monoisotopic: 291.198699805
Chemical FormulaC21H25N
InChI KeyInChIKey=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-ylmethyl)amine
SMILES
CN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Benzylamine
  • Aralkylamine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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).
PharmacodynamicsTerbinafine 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.
Mechanism of actionTerbinafine 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.
Related Articles
AbsorptionReadily absorbed from gastrointestinal tract.
Volume of distributionNot Available
Protein binding>99%
Metabolism

Hepatic

SubstrateEnzymesProduct
Terbinafine
HydroxyterbinafineDetails
Terbinafine
N-DesmethylterbinafineDetails
Terbinafine
1-NaphtaldehydeDetails
Hydroxyterbinafine
Not Available
CarboxyterbinafineDetails
Hydroxyterbinafine
Not Available
N-DesmethylhydroxyterbinafineDetails
N-Desmethylterbinafine
Not Available
N-DesmethylhydroxyterbinafineDetails
1-Naphtaldehyde
1-Naphthoic acidDetails
1-Naphtaldehyde
1-NahthalenethanolDetails
Terbinafine
Terbinafine dihydrodiol derivative (1)Details
Terbinafine
Terbinafine dihydrodiol derivative (2)Details
N-Desmethylterbinafine
Not Available
N-Desmethylterbinafine dihydrodiol derivative (1)Details
N-Desmethylterbinafine
Not Available
N-Desmethylterbinafine dihydrodiol derivative (2)Details
Terbinafine
Not Available
N-Desmethylterbinafine dihydrodiol derivative (1)Details
Terbinafine
Not Available
N-Desmethylterbinafine dihydrodiol derivative (2)Details
Route of eliminationPrior to excretion, terbinafine is extensively metabolized.
Half life36 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Fungi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Tabletoral125 mg
Granuleoral125 mg/1
Granuleoral187.5 mg/1
Spraytopical1.25 mL/125mL
Tabletoral250 mg/1
Creamtopical10 mg/g
Spraytopical1 mL/100mL
Geltopical10 mg/g
Liquidtopical1.25 mL/125mL
Creamtopical1 g/100g
Creamtopical1 %
Geltopical10 mg
Spraytopical10 mg
Tabletoral250 mg
Spraytopical1 %
Tabletoral250 1/1
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)
CA2062341 No2004-05-112012-03-05Canada
CA2068957 No2002-12-172012-05-19Canada
US5681849 No1995-04-282015-04-28Us
US5856355 No1995-05-182012-05-18Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point195-198 °CNot Available
water solubilitySlightly solubleNot Available
logP5.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000738 mg/mLALOGPS
logP5.51ALOGPS
logP5.53ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.08 m3·mol-1ChemAxon
Polarizability35.83 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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. 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 ]
  3. 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 ]
  4. Birnbaum JE: Pharmacology of the allylamines. J Am Acad Dermatol. 1990 Oct;23(4 Pt 2):782-5. [PubMed:2229523 ]
  5. McClellan KJ, Wiseman LR, Markham A: Terbinafine. An update of its use in superficial mycoses. Drugs. 1999 Jul;58(1):179-202. [PubMed:10439936 ]
  6. Krishnan-Natesan S: Terbinafine: a pharmacological and clinical review. Expert Opin Pharmacother. 2009 Nov;10(16):2723-33. doi: 10.1517/14656560903307462. [PubMed:19874252 ]
  7. Gianni C: Update on antifungal therapy with terbinafine. G Ital Dermatol Venereol. 2010 Jun;145(3):415-24. [PubMed:20461049 ]
  8. Korting HC, Kiencke P, Nelles S, Rychlik R: Comparable efficacy and safety of various topical formulations of terbinafine in tinea pedis irrespective of the treatment regimen: results of a meta-analysis. Am J Clin Dermatol. 2007;8(6):357-64. [PubMed:18039018 ]
External Links
ATC CodesD01AE15D01BA02
AHFS Codes
  • 08:14.04
  • 84:04.08.04
PDB EntriesNot Available
FDA labelDownload (137 KB)
MSDSDownload (73.2 KB)
Interactions
Drug Interactions
Drug
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Terbinafine.
AmoxapineThe metabolism of Amoxapine can be decreased when combined with Terbinafine.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Terbinafine.
AtomoxetineThe serum concentration of Atomoxetine can be increased when it is combined with Terbinafine.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Terbinafine.
ClomipramineThe metabolism of Clomipramine can be decreased when combined with Terbinafine.
CodeineThe therapeutic efficacy of Codeine can be decreased when used in combination with Terbinafine.
DesipramineThe metabolism of Desipramine can be decreased when combined with Terbinafine.
DoxepinThe metabolism of Doxepin can be decreased when combined with Terbinafine.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Terbinafine.
DuloxetineThe serum concentration of Duloxetine can be increased when it is combined with Terbinafine.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Terbinafine.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Terbinafine.
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Terbinafine.
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Terbinafine.
IloperidoneThe serum concentration of the active metabolites of Iloperidone can be increased when Iloperidone is used in combination with Terbinafine.
ImipramineThe metabolism of Imipramine can be decreased when combined with Terbinafine.
MequitazineThe serum concentration of Mequitazine can be increased when it is combined with Terbinafine.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Terbinafine.
NebivololThe serum concentration of Nebivolol can be increased when it is combined with Terbinafine.
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Terbinafine.
NortriptylineThe metabolism of Nortriptyline can be decreased when combined with Terbinafine.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Terbinafine.
PropafenoneThe serum concentration of Propafenone can be increased when it is combined with Terbinafine.
ProtriptylineThe metabolism of Protriptyline can be decreased when combined with Terbinafine.
RifampicinThe serum concentration of Terbinafine can be decreased when it is combined with Rifampicin.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Terbinafine.
TamoxifenThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Terbinafine resulting in a loss in efficacy.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Terbinafine.
TetrabenazineThe serum concentration of Tetrabenazine can be increased when it is combined with Terbinafine.
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Terbinafine.
TramadolThe therapeutic efficacy of Tramadol can be decreased when used in combination with Terbinafine.
TrimipramineThe metabolism of Trimipramine can be decreased when combined with Terbinafine.
VortioxetineThe serum concentration of Vortioxetine can be increased when it is combined with Terbinafine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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:
SQLE
Uniprot ID:
Q14534
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
Human
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinducer
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
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 gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular Weight:
60101.87 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12