U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C21H25N.ClH
Molecular Weight 327.891
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TERBINAFINE HYDROCHLORIDE

SMILES

Cl.CN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12

InChI

InChIKey=BWMISRWJRUSYEX-SZKNIZGXSA-N
InChI=1S/C21H25N.ClH/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;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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).

Originator

Sources: Proc. Int. Congr. Chemother., 13th (1983), 6, 116/47-116/51.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
30.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.7 μg/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
10.48 μg × h/mL
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16.5 day
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
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

Doses

DosePopulationAdverse 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: Page: p.155
unhealthy, 31
n = 27
Health Status: unhealthy
Condition: Eumycetoma
Age Group: 31
Sex: M+F
Population Size: 27
Sources: 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: Page: p.155
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: Page: p.6
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea
Vomiting
Abdominal pain
Dizziness
Rash
Urination frequency of
Headache
Sources: 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: Page: p.8
unhealthy
Health Status: unhealthy
Condition: Tinea|tinea pedis|tinea corporis|tinea cruris
Sources: 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: Page: p.3
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: Page: p.3
Disc. AE: Headache...
AEs leading to
discontinuation/dose reduction:
Headache (0.2%)
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: 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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.3
AEs

AEs

AESignificanceDosePopulation
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: Page: p.155
unhealthy, 31
n = 27
Health Status: unhealthy
Condition: Eumycetoma
Age Group: 31
Sex: M+F
Population Size: 27
Sources: 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: Page: p.155
unhealthy, 31
n = 27
Health Status: unhealthy
Condition: Eumycetoma
Age Group: 31
Sex: M+F
Population Size: 27
Sources: 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: Page: p.155
unhealthy, 31
n = 27
Health Status: unhealthy
Condition: Eumycetoma
Age Group: 31
Sex: M+F
Population Size: 27
Sources: 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: Page: p.155
unhealthy, 31
n = 27
Health Status: unhealthy
Condition: Eumycetoma
Age Group: 31
Sex: M+F
Population Size: 27
Sources: Page: p.155
Abdominal pain
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: Page: p.6
Dizziness
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: Page: p.6
Headache
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: Page: p.6
Nausea
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: Page: p.6
Rash
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: Page: p.6
Urination frequency of
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: Page: p.6
Vomiting
5 g single, oral
Overdose
Dose: 5 g
Route: oral
Route: single
Dose: 5 g
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.3
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.4
unhealthy
n = 465
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Population Size: 465
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: 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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Fingernail onychomycosis|Toenail onychomycosis
Sources: Page: p.3
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
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
Page: -
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes
yes
yes
yes
yes
yes
yes
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.
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.
Page: 5.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Effects of sterol inhibitors on the ATP content of Pneumocystis carinii.
1999 Sep-Oct
Synergistic interaction of terbinafine with triazoles or amphotericin B against Aspergillus species.
2001 Feb
Terbinafine resistance in a pleiotropic yeast mutant is caused by a single point mutation in the ERG1 gene.
2003 Sep 26
Ursodeoxycholic acid for terbinafine-induced toxic hepatitis.
2004 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Terbinafine-induced hepatic failure requiring liver transplantation.
2007 Jan
Terbinafine-induced acute autoimmune hepatitis in the setting of hepatitis B virus infection.
2007 May
Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata.
2009 Feb
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
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.
2014
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
Patents

Sample Use Guides

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
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 Fri Dec 15 15:24:41 UTC 2023
Edited
by admin
on Fri Dec 15 15:24:41 UTC 2023
Record UNII
012C11ZU6G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TERBINAFINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
LAMISIL
Brand Name English
TERBINAFINE (AS HYDROCHLORIDE)
Common Name English
TERBINAFINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
NSC-759113
Code English
TERBINAFINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
TERBINAFINE HYDROCHLORIDE [VANDF]
Common Name English
BRAMIZIL
Brand Name English
(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine, hydrochloride
Systematic Name English
TERBINA
Brand Name English
TERBINAFINE HYDROCHLORIDE [MI]
Common Name English
TERBINE
Brand Name English
BRAMAZIL
Brand Name English
MUZONAL
Brand Name English
TERBINAFINE HCL
Common Name English
(2E)-N,6,6-TRIMETHYL-N-(NAPHTHALEN-1-YLMETHYL)HEPT-2-EN-4-YN-1-AMINE HYDROCHLORIDE
Systematic Name English
TERBINAFINE HYDROCHLORIDE [USP-RS]
Common Name English
Terbinafine hydrochloride [WHO-DD]
Common Name English
TERBINAFINE HYDROCHLORIDE [MART.]
Common Name English
TERBINAFINE HYDROCHLORIDE [JAN]
Common Name English
1-NAPHTHALENEMETHANAMINE, N-(6,6-DIMETHYL-2-HEPTEN-4-YNYL)-N-METHYL-, (E)-, HYDROCHLORIDE
Common Name English
TERBINAFINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
Code System Code Type Description
EVMPD
SUB04723MIG
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID90229223
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
DAILYMED
012C11ZU6G
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
RXCUI
235838
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY RxNorm
CAS
78628-80-5
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
NCI_THESAURUS
C29492
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
PUBCHEM
5282481
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
DRUG BANK
DBSALT000470
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
RS_ITEM_NUM
1643496
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
NSC
759113
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
CHEBI
77614
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
FDA UNII
012C11ZU6G
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
ECHA (EC/EINECS)
616-640-4
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
ChEMBL
CHEMBL822
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
MERCK INDEX
m10569
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY Merck Index
SMS_ID
100000090624
Created by admin on Fri Dec 15 15:24:41 UTC 2023 , Edited by admin on Fri Dec 15 15:24:41 UTC 2023
PRIMARY
Related Record Type Details
SUBSTANCE ASSAY DEFINED AMOUNT->SUBSTANCE
ASSAY (TITRATION)
EP
PARENT -> SALT/SOLVATE
SUBSTANCE ASSAY DEFINED AMOUNT->SUBSTANCE
ASSAY (HPLC)
USP
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 0.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
Related Record Type Details
ACTIVE MOIETY