Identification
- Summary
Terbinafine is an allylamine antifungal used to treat dermatophyte infections of toenails and fingernails as well as other fungal skin infections.
- Brand Names
- Lamisil, Silka Cream
- Generic Name
- Terbinafine
- DrugBank Accession Number
- DB00857
- Background
Terbinafine hydrochloride (Lamisil) is a synthetic allylamine antifungal.10,11 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.1,2,11
Terbinafine hydrochloride was granted FDA approval on 30 December 1992.9
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
Structure for Terbinafine (DB00857)
- 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,11 and Tinea species.10 Terbinafine hydrochloride also treats yeast infections of the skin caused by Candida species and Malassezia furfur.11
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Onychomycosis •••••••••••• Treatment of Sporotrichosis ••• ••••• Treatment of Tinea capitis •••••••••••• ••••••• Treatment of Tinea corporis ••• ••• Treatment of Tinea cruris ••• ••• - Contraindications & Blackbox Warnings
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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.1,2,11 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.10,11 Patients taking oral terbinafine should have liver function tests performed prior to treatment to reduce the risk of liver injury.10
- 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.1,2,11 This inhibition leads to decreased ergosterol, which would normally be incorporated into the cell wall, and accumulation of squalene.2,11
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
Target Actions Organism ASqualene monooxygenase inhibitorYeast NSqualene monooxygenase inhibitorHumans - 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.10 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,10 mostly to serum albumin,8,5 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.10 However, the terminal half life ranges from 200-400 hours as it distributes into skin and adipose tissue.10 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The subcutaneous LD50 in rats and mice is >2g/kg.12 The TDLO for women is 210mg/kg/6W.12
Overdose data with terbinafine is rare, however symptoms are expected to be nausea, vomiting, abdominal pain, dizziness, rash, frequent urination, and headache.10 Treat overdose with activated charcoal as well as symptomatic and supportive therapy.11
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Terbinafine can be increased when it is combined with Abametapir. Abatacept The metabolism of Terbinafine can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Terbinafine. Abiraterone The serum concentration of Terbinafine can be increased when it is combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Terbinafine. - 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Terbinafine hydrochloride 012C11ZU6G 78628-80-5 BWMISRWJRUSYEX-SZKNIZGXSA-N - Product Images
- International/Other Brands
- Lamasil
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Terbinafine Tablet 250 mg Oral TEVA Canada Limited 2005-02-11 Not applicable Canada 
Lamisil Spray 1 % w/w Topical Novartis 1999-01-05 Not applicable Canada Lamisil Granule 187.5 mg/1 Oral Novartis Pharmaceuticals Corporation 2007-09-28 2017-05-31 US 
Lamisil Granule 125 mg/1 Oral Novartis Pharmaceuticals Corporation 2007-09-28 2017-05-31 US Lamisil Tablet 250 mg Oral Novartis 1993-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-terbinafine Tablet 250 mg Oral Apotex Corporation 2000-05-16 Not applicable Canada Auro-terbinafine Tablet 250 mg Oral Auro Pharma Inc 2011-05-30 Not applicable Canada Auro-terbinafine Tablet 125 mg Oral Auro Pharma Inc Not applicable Not applicable Canada Dom-terbinafine Tablet 250 mg Oral Dominion Pharmacal 2011-03-03 Not applicable Canada Jamp-terbinafine Tablet 250 mg Oral Jamp Pharma Corporation 2010-10-24 2022-09-07 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Antifungal Cream 1 g/100g Topical Meijer Distribution Inc 2007-07-02 Not applicable US Antifungal Foot Cream 1 g/100g Topical American Sales Company 2007-07-02 Not applicable US Athletes Foot Cream 1 g/100g Topical Publix Super Markets Inc. 2007-07-02 Not applicable US Athletes Foot Cream 1 g/100g Topical H E B 2007-07-02 Not applicable US Athletes Foot Cream 1 g/100g Topical TARGET Corporation 2007-07-02 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image M-FURO MANT % 0.1 + % 1 KREM, 20G Terbinafine hydrochloride (10 mg/g) + Mometasone furoate (1 mg/g) Cream Topical ORVA İLAÇ SAN. VE TİC. A.Ş. 2015-12-17 Not applicable Turkey 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ciclopirox 8% / Fluconazole 1% / Terbinafine HCl 1% Terbinafine (1 g/100g) + Ciclopirox (8 g/100g) + Fluconazole (1 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-01 Not applicable US 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) Solution Topical Sincerus Florida, LLC 2019-05-01 Not applicable US Onycho-Med Terbinafine hydrochloride (250 mg/10mL) + Miconazole nitrate (200 mg/10mL) Kit Topical Medhart Pharmaceuticals, Inc. 2019-05-30 Not applicable US Terbinafine HCl 5% Terbinafine hydrochloride (5 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-21 Not applicable US Terbinafine HCl Chlortimazole and Tolnaftate Terbinafine hydrochloride (1 g/100mL) + Clotrimazole (1 g/100mL) + Tolnaftate (1 g/100mL) Solution Topical Dr Marc's Manufacturing And Sales 2018-01-30 2018-04-17 US
Categories
- ATC Codes
- D01AE15 — Terbinafine
- D01AE — Other antifungals for topical use
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- Drug Categories
- Agents Causing Muscle Toxicity
- Allylamine Antifungal
- Allylamines
- Anti-Infective Agents
- Antifungal Agents
- Antifungals for Dermatological Use
- Antifungals for Systemic Use
- Antifungals for Topical Use
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (weak)
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Enzyme Inhibitors
- Naphthalenes
- 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)
- Affected organisms
- Fungi
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
- 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. [Article]
- Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7. [Article]
- 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. [Article]
- 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. [Article]
- Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Topical Cream (Discontinued) [Link]
- FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
- Health Canada Approved Drug Products: Lamisil Terbinafine Oral Tablets, Topical Cream, and Topical Spray [Link]
- Cayman Chemicals: Terbinafine MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0014995
- KEGG Drug
- D02375
- KEGG Compound
- C08079
- PubChem Compound
- 1549008
- PubChem Substance
- 46508519
- ChemSpider
- 1266005
- BindingDB
- 50018518
- 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
- FDA label
- Download (137 KB)
- MSDS
- Download (73.2 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Onychomycosis 1 3 Active Not Recruiting Treatment Onychomycosis 1 3 Completed Not Available Distal, Subungual Onychomycosis 1 3 Completed Treatment Dermatophyte Infection / Itraconazole Adverse Reaction / Terbinafine Adverse Reaction 1 3 Completed Treatment Distal, Subungual Onychomycosis 1
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
Form Route Strength Suspension Topical 1 % w/v Cream Topical 10 mg/1g Tablet Oral 125 mg Gel Cutaneous Cream Topical 10 mg/g Cream Cutaneous 1.000 g Tablet Oral 250.000 mg Gel Topical 1 mg Gel Topical 100000 mg Solution Topical Lotion Topical 1 % Gel Topical Cream Topical 1 g Solution Topical 1 g Cream Topical 1 g/100g Cream 1.000 g Tablet Oral Solution Topical 1.028 g Solution Topical 1.05 g Cream Topical 1 % Gel Cutaneous 1 % Granule Oral 125 mg/1 Granule Oral 187.5 mg/1 Spray Topical 1.25 mL/125mL Solution Topical 40 mg Gel Topical 1 % Solution Topical Solution Topical 1.125 g Tablet Oral 250 mg Aerosol, spray Topical 0.84 g/125mL Spray Topical 1 mL/100mL Spray Topical 1 g/100mL Gel Topical 10 mg/1g Liquid Topical 0.84 g/125mL Cream Topical 1 % w/w Gel Topical 10 mg / g Gel Topical 1 %w/w Solution Topical 10 mg/g Spray Topical 10 mg/g Tablet, film coated Oral 250 mg Solution Topical 100000 g Solution Topical 1 % Gel Cutaneous 1.000 g Cream Topical 0.00888 g Solution Cutaneous 0.888 g Tablet Oral 281.296 mg Cream Topical Cream Topical Solution Topical 10 mg Tablet Oral 500 mg Cream Topical 8.880 mg Cream Cutaneous 10.00 mg Lotion Topical Solution Topical 78.22 MG/ML Kit Topical Powder Topical 1 g Powder Topical 100000 g Spray Topical 1 % Gel Cutaneous 1.00 g Ointment Topical Gel Topical 1 g/100g Gel Topical 1.000 g Aerosol Cutaneous 1.000 g Cream Topical 1.000 % w/w Spray Topical Spray Topical 1 % w/w Gel Topical Gel Topical 1000 mg Lotion Topical 1 g Solution Topical 98 mg/ml Tablet, coated Oral 250 mg Aerosol Topical 1 g Tablet Oral 25000000 mg Solution Topical 5 g/100g Tablet Oral 250 1/1 Tablet Oral 250 mg/1 Gel Topical 1 g Aerosol Topical 1 % w/w Suspension Cutaneous 8.880 mg Solution Cutaneous 1.000 g Cream Topical 1 %w/w - Prices
Unit description Cost Unit LamISIL 14 187.5 mg Packets Packet 202.16USD packet LamISIL 1% Solution 30ml Bottle 88.18USD bottle Terbinafine hcl powder 42.84USD g Terbinafine HCl 1% Cream 24 gm Tube 17.99USD tube Lamisil 250 mg tablet 14.22USD tablet Terbinafine hcl 250 mg tablet 13.19USD tablet Lamisil 250 mg Tablet 4.79USD tablet Apo-Terbinafine 250 mg Tablet 2.64USD tablet Co Terbinafine 250 mg Tablet 2.64USD tablet Mylan-Terbinafine 250 mg Tablet 2.64USD tablet Novo-Terbinafine 250 mg Tablet 2.64USD tablet Pms-Terbinafine 250 mg Tablet 2.64USD tablet Sandoz Terbinafine 250 mg Tablet 2.64USD tablet Lamisil 1% cream 2.13USD g Lamisil 1 % Solution 0.58USD g Lamisil 1 % Cream 0.57USD g Sm athlete's 1% foot cream 0.53USD g Lamisil at 1% cream 0.51USD g CVS Pharmacy jock itch 1% cream 0.49USD g CVS Pharmacy athlete's foot 1% cream 0.4USD g Athlete's 1% foot cream 0.27USD g Lamisil af defense crm to powd 0.2USD g Lamisil antifungal 1% spray 0.07USD ml Lamisil af defense 1% powder 0.05USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5681849 No 1997-10-28 2015-04-28 US US5856355 No 1999-01-05 2012-05-18 US CA2062341 No 2004-05-11 2012-03-05 Canada CA2068957 No 2002-12-17 2012-05-19 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 205 Health Canada boiling point (°C) 417.9 ChemSpider water solubility 0.63% Health Canada pKa 7.10 Health Canada - Predicted Properties
Property Value Source Water Solubility 0.000738 mg/mL ALOGPS logP 5.51 ALOGPS logP 5.53 Chemaxon logS -5.6 ALOGPS pKa (Strongest Basic) 8.86 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 3.24 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 98.08 m3·mol-1 Chemaxon Polarizability 35.84 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9876 Blood Brain Barrier + 0.9381 Caco-2 permeable + 0.7436 P-glycoprotein substrate Substrate 0.6026 P-glycoprotein inhibitor I Non-inhibitor 0.7495 P-glycoprotein inhibitor II Inhibitor 0.8205 Renal organic cation transporter Non-inhibitor 0.581 CYP450 2C9 substrate Non-substrate 0.7806 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6461 CYP450 1A2 substrate Non-inhibitor 0.5 CYP450 2C9 inhibitor Non-inhibitor 0.8951 CYP450 2D6 inhibitor Inhibitor 0.6772 CYP450 2C19 inhibitor Non-inhibitor 0.6194 CYP450 3A4 inhibitor Non-inhibitor 0.6314 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5884 Ames test Non AMES toxic 0.8736 Carcinogenicity Carcinogens 0.5109 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.8932 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8785 hERG inhibition (predictor II) Non-inhibitor 0.5566
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 189.225326 predictedDarkChem Lite v0.1.0 [M-H]- 195.322526 predictedDarkChem Lite v0.1.0 [M-H]- 167.96605 predictedDeepCCS 1.0 (2019) [M+H]+ 189.259726 predictedDarkChem Lite v0.1.0 [M+H]+ 196.170226 predictedDarkChem Lite v0.1.0 [M+H]+ 170.32405 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.570026 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.466626 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.41719 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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. [Article]
- Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7. [Article]
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7. [Article]
- Krishnan-Natesan S: Terbinafine: a pharmacological and clinical review. Expert Opin Pharmacother. 2009 Nov;10(16):2723-33. doi: 10.1517/14656560903307462. [Article]
Enzymes
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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. [Article]
- Debruyne D, Coquerel A: Pharmacokinetics of antifungal agents in onychomycoses. Clin Pharmacokinet. 2001;40(6):441-72. [Article]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
- 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
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- 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. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- 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. [Article]
- 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
- 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. [Article]
- FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- FDA Approved Drug Products: Lamisil Terbinafine Hydrochloride Oral Tablets [Link]
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
- 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. [Article]
- Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [Article]
- 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
- Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. [Article]
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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54