Explore a selection of our essential drug information below, or:
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
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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
- 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.
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 Italia S.R.L. 2005-02-11 Not applicable Canada 
Lamisil Tablet 250 mg/1 Oral Novartis Farma S.P.A. 1996-05-10 2018-10-31 US 
Lamisil Spray 1 % w/w Topical Novartis 1999-01-05 Not applicable Canada Lamisil Granule 187.5 mg/1 Oral Novartis Farma S.P.A. 2007-09-28 2017-05-31 US Lamisil Granule 125 mg/1 Oral Novartis Farma S.P.A. 2007-09-28 2017-05-31 US - 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 125 mg Oral Auro Pharma Inc Not applicable Not applicable Canada Auro-terbinafine Tablet 250 mg Oral Auro Pharma Inc 2011-05-30 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 H E B 2007-07-02 Not applicable US Athletes Foot Cream 10 mg/1g Topical TARGET Corporation 2009-08-31 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Nail Diseases / Onychomycosis / Resistant Infection 1 somestatus stop reason just information to hide Not Available Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Oral Candidiasis 1 somestatus stop reason just information to hide Not Available Completed Treatment Onychomycosis 2 somestatus stop reason just information to hide Not Available Unknown Status Treatment Onychomycosis / Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide 4 Completed Treatment Onychomycosis 1 somestatus stop reason just information to hide
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 Cream Topical 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 % Cream Topical Gel Topical Cream Topical 1 g Solution Topical 1 g Cream Topical 1 g/100g Cream Topical 10 mg Cream 1.000 g 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 Cutaneous 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 Solution Topical 10 mg Tablet Oral 500 mg Cream Topical 8.880 mg Cream Cutaneous 10.00 mg Gel Topical 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 1 % w/w 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 Tablet Oral Solution Topical 5 g/100g Tablet Oral 250 1/1 Tablet Oral 250 mg/1 Cream 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 epoxidase; part of the third module of ergosterol biosynthesis pathway that includes the late steps of the pathway (PubMed:15845783, PubMed:3877503, PubMed:6378256, PubMed:9161422). Erg1 catalyzes the epoxidation of squalene into 2,3-epoxysqualene (PubMed:15845783, PubMed:3877503, PubMed:6378256, PubMed:9161422). The third module or late pathway involves the ergosterol synthesis itself through consecutive reactions that mainly occur in the endoplasmic reticulum (ER) membrane. Firstly, the squalene synthase ERG9 catalyzes the condensation of 2 farnesyl pyrophosphate moieties to form squalene, which is the precursor of all steroids. Squalene synthase is crucial for balancing the incorporation of farnesyl diphosphate (FPP) into sterol and nonsterol isoprene synthesis. Secondly, the squalene epoxidase ERG1 catalyzes the stereospecific oxidation of squalene to (S)-2,3-epoxysqualene, which is considered to be a rate-limiting enzyme in steroid biosynthesis. Then, the lanosterol synthase ERG7 catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol core. In the next steps, lanosterol is transformed to zymosterol through a complex process involving various demethylation, reduction and desaturation reactions. The lanosterol 14-alpha-demethylase ERG11 (also known as CYP51) catalyzes C14-demethylation of lanosterol to produce 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol, which is critical for ergosterol biosynthesis. The C-14 reductase ERG24 reduces the C14=C15 double bond of 4,4-dimethyl-cholesta-8,14,24-trienol to produce 4,4-dimethyl-cholesta-8,24-dienol. 4,4-dimethyl-cholesta-8,24-dienol is substrate of the C-4 demethylation complex ERG25-ERG26-ERG27 in which ERG25 catalyzes the three-step monooxygenation required for the demethylation of 4,4-dimethyl and 4alpha-methylsterols, ERG26 catalyzes the oxidative decarboxylation that results in a reduction of the 3-beta-hydroxy group at the C-3 carbon to an oxo group, and ERG27 is responsible for the reduction of the keto group on the C-3. ERG28 has a role as a scaffold to help anchor ERG25, ERG26 and ERG27 to the endoplasmic reticulum and ERG29 regulates the activity of the iron-containing C4-methylsterol oxidase ERG25. Then, the sterol 24-C-methyltransferase ERG6 catalyzes the methyl transfer from S-adenosyl-methionine to the C-24 of zymosterol to form fecosterol. The C-8 sterol isomerase ERG2 catalyzes the reaction which results in unsaturation at C-7 in the B ring of sterols and thus converts fecosterol to episterol. The sterol-C5-desaturase ERG3 then catalyzes the introduction of a C-5 double bond in the B ring to produce 5-dehydroepisterol. The C-22 sterol desaturase ERG5 further converts 5-dehydroepisterol into ergosta-5,7,22,24(28)-tetraen-3beta-ol by forming the C-22(23) double bond in the sterol side chain. Finally, ergosta-5,7,22,24(28)-tetraen-3beta-ol is substrate of the C-24(28) sterol reductase ERG4 to produce ergosterol (Probable).
- Specific Function
- flavin adenine dinucleotide binding
- 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
- Catalyzes the stereospecific oxidation of squalene to (S)-2,3-epoxysqualene, and is considered to be a rate-limiting enzyme in steroid biosynthesis
- Specific Function
- FAD binding
- 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
- Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). 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 generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
- Specific Function
- heme binding
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 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
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 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
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- 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
- Functions as a 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 the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction
- Specific Function
- Not Available
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
- ABC-type transporter activity
- 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 October 10, 2024 16:46