TERBINAFINE, (Z)-

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-UITAMQMPSA-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 8297		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 8429	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 8.9380802E11

C_max

Value	Dose	Analyte	Population
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
1.34 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 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
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
4.74 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
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 Page: p.155	unhealthy, 31 n = 27 Health Status: unhealthy Condition: Eumycetoma Age Group: 31 Sex: M+F Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/16445509 Page: p.155	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 Page: p.155
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 Page: p.6	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.6	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 Page: p.6
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 Page: p.8	unhealthy Health Status: unhealthy Condition: Tinea\|tinea pedis\|tinea corporis\|tinea cruris Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20846s001lbl.pdf Page: p.8	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20846s001lbl.pdf Page: p.8
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 Page: p.3	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.3	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 Page: p.3
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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4	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 Page: p.4
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1	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 Page: p.1
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 Page: p.3	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.3	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 Page: p.3

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1054 CYP2C8 693 CYP2C19 991 CYP2B6 664

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1891	inhibitor 3277 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 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10460803/ Page: -	yes	Hydroxyterbinafine 4
CYP2C9 1037	substrate 3367 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 1737	substrate 3367 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 1647	inhibitor 1626 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
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
eMolecules	902552	https://www.emolecules.com/cgi-bin/more?vid=902552

PubMed

Title	Date	PubMed
Effects of naftifine and terbinafine, two allylamine antifungal drugs, on selected functions of human polymorphonuclear leukocytes.	1994 Nov	7872755
Activity of terbinafine against Pneumocystis carinii in vitro and its efficacy in the treatment of experimental pneumonia.	1994 Nov	7706168
Terbinafine-induced cholestatic liver disease.	1996 Jun	8835752
Safety of oral terbinafine: results of a postmarketing surveillance study in 25,884 patients.	1997 Oct	9382559
Terbinafine. An update of its use in superficial mycoses.	1999 Jul	10439936
Synergy between 6-amino-2-n-pentylthiobenzothiazole and ergosterol biosynthesis-inhibiting antimycotics against Candida albicans in vitro.	2000 Jul	10854813
Inhibitors of sterol biosynthesis and amphotericin B reduce the viability of pneumocystis carinii f. sp. carinii.	2000 Jun	10817720
Use of terbinafine in mouse and rat models of Pneumocystis carinii pneumonia.	2002 Feb	11796365
Terbinafine: a review of its use in onychomycosis in adults.	2003	12477372
Terbinafine resistance in a pleiotropic yeast mutant is caused by a single point mutation in the ERG1 gene.	2003 Sep 26	12963042
Ursodeoxycholic acid for terbinafine-induced toxic hepatitis.	2004 Jun	15122001
Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality.	2005 Dec	18360572
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Terbinafine inhibits endothelial cell migration through suppression of the Rho-mediated pathway.	2006 Dec	17172416
Synthesis and SAR studies of biaryloxy-substituted triazoles as antifungal agents.	2008 Jun 1	18467095
Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata.	2009 Feb	19096993
Terbinafine: a pharmacological and clinical review.	2009 Nov	19874252
Update on antifungal therapy with terbinafine.	2010 Jun	20461049
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 Nov	20875694
Hippolachnin A, a new antifungal polyketide from the South China Sea sponge Hippospongia lachne.	2013 Jul 19	23829334
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903
Arachidonic acid affects biofilm formation and PGE2 level in Candida albicans and non-albicans species in presence of subinhibitory concentration of fluconazole and terbinafine.	2014 May-Jun	24389279
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

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 `Sat Dec 16 09:11:18 UTC 2023` Edited by `admin` on `Sat Dec 16 09:11:18 UTC 2023`
Record UNII	S76S370M70
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TERBINAFINE, (Z)-

Common Name

English

CIS-TERBINAFINE

Common Name

English

TERBINAFINE RELATED COMPOUND B FREE BASE

Common Name

English

TERBINAFINE HYDROCHLORIDE IMPURITY, CIS-TERBINAFINE- [USP IMPURITY]

Common Name

English

(2Z)-N,6,6-TRIMETHYL-N-(NAPHTHALEN-1-YLMETHYL)HEPT-2-EN-4-YN-1-AMINE

Systematic Name

English

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

Systematic Name

English

TERBINAFINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]

Common Name

English

Code System Code Type Description

CAS

78628-81-6

Created by admin on Sat Dec 16 09:11:18 UTC 2023 , Edited by admin on Sat Dec 16 09:11:18 UTC 2023

PRIMARY

FDA UNII

S76S370M70

Created by admin on Sat Dec 16 09:11:18 UTC 2023 , Edited by admin on Sat Dec 16 09:11:18 UTC 2023

PRIMARY

PUBCHEM

1549006

Created by admin on Sat Dec 16 09:11:18 UTC 2023 , Edited by admin on Sat Dec 16 09:11:18 UTC 2023

PRIMARY

Related Record Type Details


					2H771UZ786

TERBINAFINE HYDROCHLORIDE, (Z)-

SALT/SOLVATE -> PARENT

Amount:

Related Record Type Details


					012C11ZU6G

TERBINAFINE HYDROCHLORIDE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

AE	Significance	Dose	Population
Glutamic-oxaloacetic transaminase increased	3.7% Disc. AE	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 Page: p.155	unhealthy, 31 n = 27 Health Status: unhealthy Condition: Eumycetoma Age Group: 31 Sex: M+F Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/16445509 Page: p.155
Neutropenia	3.7% Disc. AE	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 Page: p.155	unhealthy, 31 n = 27 Health Status: unhealthy Condition: Eumycetoma Age Group: 31 Sex: M+F Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/16445509 Page: p.155
Serum glutamic-pyruvic transaminase increased	3.7% Disc. AE	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 Page: p.155	unhealthy, 31 n = 27 Health Status: unhealthy Condition: Eumycetoma Age Group: 31 Sex: M+F Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/16445509 Page: p.155
Neutropenia	7.4% Disc. AE	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 Page: p.155	unhealthy, 31 n = 27 Health Status: unhealthy Condition: Eumycetoma Age Group: 31 Sex: M+F Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/16445509 Page: p.155
Abdominal pain		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 Page: p.6	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.6
Dizziness		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 Page: p.6	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.6
Headache		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 Page: p.6	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.6
Nausea		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 Page: p.6	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.6
Rash		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 Page: p.6	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.6
Urination frequency of		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 Page: p.6	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.6
Vomiting		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 Page: p.6	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.6
Headache	0.2% Disc. AE	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 Page: p.3	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.3
Liver enzyme abnormal	0.2% Disc. AE	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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4
Nausea	0.2% Disc. AE	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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4
Pruritus	0.2% Disc. AE	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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4
Taste disturbance	0.2% Disc. AE	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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4
Abdominal pain	0.4% Disc. AE	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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4
Dyspepsia	0.4% Disc. AE	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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4
Diarrhea	0.6% Disc. AE	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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4
Rash	0.9% Disc. AE	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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4
Visual disturbance	0.9% Disc. AE	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 Page: p.4	unhealthy n = 465 Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.4
Bullous dermatitis	Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Depressive symptom	Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Drug reaction with eosinophilia and systemic symptoms	Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Erythema multiforme	Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Exfoliative dermatitis	Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Liver failure	Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Smell alteration	Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Stevens-Johnson syndrome	Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Toxic epidermal necrolysis	Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Neutropenia	severe Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Taste disturbance	severe Disc. AE	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 Page: p.1	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.1
Hemolytic uremic syndrome	Disc. AE	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 Page: p.3	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.3
Lupus erythematosus	Disc. AE	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 Page: p.3	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.3
Thrombotic microangiopathy	Disc. AE	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 Page: p.3	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.3
Thrombotic thrombocytopenic purpura	Disc. AE	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 Page: p.3	unhealthy Health Status: unhealthy Condition: Fingernail onychomycosis\|Toenail onychomycosis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020539s029,022071s013lbl.pdf Page: p.3

Details

SMILES

InChI

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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2

F_unbound

Drug as perpetrator