TERBINAFINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H25N
Molecular Weight	291.4299
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C\C=C\C#CC(C)(C)C)CC1=C2C=CC=CC2=CC=C1

InChI

InChIKey=DOMXUEMWDBAQBQ-WEVVVXLNSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C21H25N
Molecular Weight	291.4299
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf

Terbinafine (brand name Lamisil, Terbisil, Terboderm and others) is an antifungal medication used to treat ringworm and fungal nail infections. Terbinafine inhibits ergosterol synthesis by inhibiting squalene epoxidase, an enzyme that is part of the fungal cell membrane synthesis pathway. Because terbinafine prevents the conversion of squalene to lanosterol, ergosterol cannot be synthesized. This is thought to change cell membrane permeability, causing fungal cell lysis. Many side effects and adverse drug reactions have been reported with oral terbinafine hydrochloride possibly due to its extensive biodistribution and the often extended durations involved in antifungal treatment (longer than two months).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Squalene monooxygenase 10 Target ID: CHEMBL1888 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21229992	Inhibitor 8504		30.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Onychomycosis 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	Curative		Approved 8583	LAMISIL Approved Use Uses cures most athlete’s foot (tinea pedis) between the toes.Effectiveness on the bottom or sides of foot is unknown. cures most jock itch (tinea cruris) and ringworm (tinea corporis) relieves itching, burning, cracking and scaling which accompany these conditions Launch Date 1998

C_max

Value	Dose	Analyte	Population
1.34 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8593011/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	TERBINAFINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8593011/	250 mg 1 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TERBINAFINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020539s021lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	TERBINAFINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
4.74 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8593011/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	TERBINAFINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.48 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8593011/	250 mg 1 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TERBINAFINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.56 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020539s021lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	TERBINAFINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.5 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8593011/	250 mg 1 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered:		TERBINAFINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
36 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020539s021lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		TERBINAFINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020539s021lbl.pdf	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		TERBINAFINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
500 mg 2 times / day multiple, oral Highest studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16445509	unhealthy, 31 Health Status: unhealthy Age Group: 31 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16445509	Disc. AE: Neutropenia, Neutropenia... AEs leading to discontinuation/dose reduction: Neutropenia (7.4%) Neutropenia (3.7%) Glutamic-oxaloacetic transaminase increased (3.7%) Serum glutamic-pyruvic transaminase increased (3.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/16445509
5 g single, oral Overdose Dose: 5 g Route: oral Route: single Dose: 5 g Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	Other AEs: Nausea, Vomiting... Other AEs: Nausea Vomiting Abdominal pain Dizziness Rash Urination frequency of Headache Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf
1 % 1 times / day multiple, topical Recommended Dose: 1 %, 1 times / day Route: topical Route: multiple Dose: 1 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20846s001lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20846s001lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20846s001lbl.pdf
250 mg 1 times / day multiple, oral Recommended Dose: 250 mg, 1 times / day Route: oral Route: multiple Dose: 250 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	Disc. AE: Liver failure, Taste disturbance... AEs leading to discontinuation/dose reduction: Liver failure Taste disturbance (severe) Smell alteration Depressive symptom Neutropenia (severe) Stevens-Johnson syndrome Toxic epidermal necrolysis Erythema multiforme Exfoliative dermatitis Bullous dermatitis Drug reaction with eosinophilia and systemic symptoms Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf
250 mg 1 times / day multiple, oral Recommended Dose: 250 mg, 1 times / day Route: oral Route: multiple Dose: 250 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	Disc. AE: Lupus erythematosus, Thrombotic microangiopathy... AEs leading to discontinuation/dose reduction: Lupus erythematosus Thrombotic microangiopathy Thrombotic thrombocytopenic purpura Hemolytic uremic syndrome Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf
250 mg 1 times / day multiple, oral Recommended Dose: 250 mg, 1 times / day Route: oral Route: multiple Dose: 250 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (0.2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf
250 mg 1 times / day multiple, oral Recommended Dose: 250 mg, 1 times / day Route: oral Route: multiple Dose: 250 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf	Disc. AE: Diarrhea, Dyspepsia... AEs leading to discontinuation/dose reduction: Diarrhea (0.6%) Dyspepsia (0.4%) Abdominal pain (0.4%) Nausea (0.2%) Rash (0.9%) Pruritus (0.2%) Liver enzyme abnormal (0.2%) Taste disturbance (0.2%) Visual disturbance (0.9%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1197 CYP2C8 810 CYP2C19 1119 CYP2B6 776

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes [Ki 0.03 uM]		yes (co-administration study) Comment: In studies in healthy subjects characterized as extensive metabolizers of dextromethorphan (antitussive drug and CYP2D6 probe substrate), terbinafine increases the dextromethorphan/ dextrorphan metabolite ratio in urine by 16- to 97-fold on average Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes		yes (co-administration study) Comment: Coadministration of a single dose of fluconazole (100 mg) with a single dose of terbinafine resulted in a 52% and 69% increase in terbinafine Cmax and AUC, respectively. Fluconazole is an inhibitor of CYP2C9 and CYP3A enzymes. Based on this finding, it is likely that other inhibitors of both CYP2C9 and CYP3A4 (e.g., ketoconazole, amiodarone) may also lead to a substantial increase in the systemic exposure (Cmax and AUC) of terbinafine when concomitantly administered. Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020539s033lbl.pdf#page=5 Page: 5.0	yes		yes (co-administration study) Comment: Coadministration of a single dose of fluconazole (100 mg) with a single dose of terbinafine resulted in a 52% and 69% increase in terbinafine Cmax and AUC, respectively. Fluconazole is an inhibitor of CYP2C9 and CYP3A enzymes. Based on this finding, it is likely that other inhibitors of both CYP2C9 and CYP3A4 (e.g., ketoconazole, amiodarone) may also lead to a substantial increase in the systemic exposure (Cmax and AUC) of terbinafine when concomitantly administered. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020539s033lbl.pdf#page=5 Page: 5.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/12729675/ Page: -

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9448	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9448
eMolecules	902552	https://www.emolecules.com/cgi-bin/more?vid=902552
MolPort	MolPort-002-507-761	https://www.molport.com/shop/molecule-link/MolPort-002-507-761
Selleck Chemicals	Terbinafine(Lamisil)	http://www.selleckchem.com/products/Terbinafine(Lamisil).html
ZINC	ZINC000001530981	http://zinc15.docking.org/substances/ZINC000001530981

PubMed

Title	Date	PubMed
A metoprolol-terbinafine combination induced bradycardia.	2015-09	24894748
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
Identification and antifungal susceptibility of fungi isolated from dermatomycoses.	2014-05	23556501
Synthesis, antifungal activities and molecular docking studies of novel 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl dithiocarbamates.	2014-03-03	24487187
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.	2014-01	24085192
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.	2014	25058030
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013-09-05	23769903
Hippolachnin A, a new antifungal polyketide from the South China Sea sponge Hippospongia lachne.	2013-07-19	23829334
Assessment of phytochemicals, antimicrobial and cytotoxic activities of extract and fractions from Fagonia olivieri (Zygophyllaceae).	2013-07-10	23842440
Arachidonic acid affects biofilm formation and PGE2 level in Candida albicans and non-albicans species in presence of subinhibitory concentration of fluconazole and terbinafine.	2013-05-26	24389279
In vitro antifungal susceptibility of clinically relevant species belonging to Aspergillus section Flavi.	2013-04	23335742
Development of a highly sensitive cytotoxicity assay system for CYP3A4-mediated metabolic activation.	2011-08	21540358
Synthesis and in-vitro antimicrobial activity of secondary and tertiary amines containing 2-chloro-6-methylquinoline moiety.	2011-07	21618272
Efficient synthesis of novel 1,2,4-triazole fused acyclic and 21-28 membered macrocyclic and/or lariat macrocyclic oxaazathia crown compounds with potential antimicrobial activity.	2010-11	20875694
Isavuconazole: a comprehensive review of spectrum of activity of a new triazole.	2010-11	20524153
Terbinafine stimulates the pro-inflammatory responses in human monocytic THP-1 cells through an ERK signaling pathway.	2010-10-23	20816994
Update on antifungal therapy with terbinafine.	2010-06	20461049
Fungicide activity of 5-(4-chlorobenzylidene)-(Z)-2-dimethylamino-1,3-thiazol-4-one against Cryptococcus neoformans.	2010-01	19927310
Terbinafine: a pharmacological and clinical review.	2009-11	19874252
Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata.	2009-02	19096993
Terbinafine hydrochloride oral granules versus oral griseofulvin suspension in children with tinea capitis: results of two randomized, investigator-blinded, multicenter, international, controlled trials.	2008-07	18378354
Synthesis and SAR studies of biaryloxy-substituted triazoles as antifungal agents.	2008-06-01	18467095
Synthesis of new N-phenylpyrazole derivatives with potent antimicrobial activity.	2008-04-15	18313934
Terbinafine-induced acute generalized exanthematous pustulosis.	2008-04	18833041
N- and S-alpha-l-arabinopyranosyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles. First synthesis and biological evaluation.	2007-09	17408811
Terbinafine-induced acute autoimmune hepatitis in the setting of hepatitis B virus infection.	2007-05	17426078
Terbinafine-induced hepatic failure requiring liver transplantation.	2007-01	17192859
Comparable efficacy and safety of various topical formulations of terbinafine in tinea pedis irrespective of the treatment regimen: results of a meta-analysis.	2007	18039018
Terbinafine inhibits endothelial cell migration through suppression of the Rho-mediated pathway.	2006-12	17172416
Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality.	2005-12	18360572
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
[Colestasic toxic hepatitis caused by terbinafine: case report].	2004-12-23	15614306
Ursodeoxycholic acid for terbinafine-induced toxic hepatitis.	2004-06	15122001
[Antimycotics suppress interleukin-4 and interleukin-5 production in anti-CD3 plus anti-CD28-stimulated T cells from patients with atopic dermatitis].	2004	15284827
Terbinafine resistance in a pleiotropic yeast mutant is caused by a single point mutation in the ERG1 gene.	2003-09-26	12963042
Ergosterol biosynthesis inhibitors become fungicidal when combined with calcineurin inhibitors against Candida albicans, Candida glabrata, and Candida krusei.	2003-03	12604527
In vitro activities of terbinafine against cutaneous isolates of Candida albicans and other pathogenic yeasts.	1998-05	9593126
Comparative study of antifungal activity of sertaconazole, terbinafine, and bifonazole against clinical isolates of Candida spp., Cryptococcus neoformans and dermatophytes.	1997-12-13	9395851
Safety of oral terbinafine: results of a postmarketing surveillance study in 25,884 patients.	1997-10	9382559
Terbinafine-induced prolonged cholestasis with reduction of interlobular bile ducts.	1997-07	9246051
Terbinafine-induced cholestatic liver disease.	1996-06	8835752
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.	1995-11-24	7490723
[Ageusia caused by terbinafine].	1995-09-09	7475473
Effects of naftifine and terbinafine, two allylamine antifungal drugs, on selected functions of human polymorphonuclear leukocytes.	1994-11	7872755
Activity of terbinafine against Pneumocystis carinii in vitro and its efficacy in the treatment of experimental pneumonia.	1994-11	7706168
Synthesis and structure-activity relationships of phenyl-substituted benzylamine antimycotics: a novel benzylbenzylamine antifungal agent for systemic treatment.	1993-07-23	8340915
Terbinafine: mode of action and properties of the squalene epoxidase inhibition.	1992-02	1543672
Pharmacology of the allylamines.	1990-10	2229523
Antifungal activity of the allylamine derivative terbinafine in vitro.	1987-09	3674847
Synthesis and antifungal activity of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphtha lenemethanamine (SF 86-327) and related allylamine derivatives with enhanced oral activity.	1984-12	6502589

Patents

Sample Use Guides

In Vivo Use Guide

Prior to administering, evaluate patients for evidence of chronic or active liver disease. Fingernail onychomycosis: One 250 mg tablet, once daily for 6 weeks. Toenail onychomycosis: One 250 mg tablet, once daily for 12 weeks.

Route of Administration: Oral

In Vitro Use Guide

TRB (Terbinafine) were diluted 100-fold in dimethyl sulfoxide to obtain stock solutions that were kept at -20ºC. The antifungals were diluted in RPMI-1640 medium (Sigma Chemical Co, Missouri, USA) at pH 7.0 buffered with 0.16 M morpholinepropanesulfonic acid to obtain final concentrations ranging from 0.03-16 μg/mL for TRB. The diluted antifungal suspensions were then added to 96-well microtitre trays. Next, each fungal suspension was inoculated into the appropriate well at final concentrations ranging from 0.5 x 10^3-2.5 x 10^3 CFU/mL. The minimum inhibitory concentration (MIC) of each antifungal was determined by spectrophotometric reading at 492 nm following incubation at 35ºC for 72 h.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:54 GMT 2025`
Record UNII	G7RIW8S0XP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TERBINAFINE

Official Name

English

LAMASIL

Preferred Name

English

TERBINAFINE [EMA EPAR VETERINARY]

Common Name

English

SF-86-327

Code

English

OSURNIA COMPONENT TERBINAFINE

Brand Name

English

TERBINAFINE [USAN]

Common Name

English

terbinafine [INN]

Common Name

English

TERBINAFINE [MART.]

Common Name

English

SF 86-327

Code

English

1-NAPHTHALENEMETHANAMINE, N-(6,6-DIMETHYL-2-HEPTEN-4-YNYL)-N-METHYL-, (E)-

Common Name

English

TERBINAFINE [VANDF]

Common Name

English

TERBINAFINE [MI]

Common Name

English

(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine

Systematic Name

English

TERBINAFINE [GREEN BOOK]

Common Name

English

TERBINAFINE [ORANGE BOOK]

Common Name

English

Terbinafine [WHO-DD]

Common Name

English

TDT-067

Code

English

Classification Tree Code System Code

NDF-RT

N0000175874