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Details

Stereochemistry ACHIRAL
Molecular Formula C21H25N
Molecular Weight 291.4307
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TERBINAFINE

SMILES

CC(C)(C)C#C/C(/[H])=C(\[H])/CN(C)Cc1cccc2ccccc21

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 291.4307
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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
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 Dec
Antifungal activity of the allylamine derivative terbinafine in vitro.
1987 Sep
Pharmacology of the allylamines.
1990 Oct
Terbinafine: mode of action and properties of the squalene epoxidase inhibition.
1992 Feb
Synthesis and structure-activity relationships of phenyl-substituted benzylamine antimycotics: a novel benzylbenzylamine antifungal agent for systemic treatment.
1993 Jul 23
Effects of naftifine and terbinafine, two allylamine antifungal drugs, on selected functions of human polymorphonuclear leukocytes.
1994 Nov
Activity of terbinafine against Pneumocystis carinii in vitro and its efficacy in the treatment of experimental pneumonia.
1994 Nov
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.
1995 Nov 24
[Ageusia caused by terbinafine].
1995 Sep 9
Terbinafine-induced cholestatic liver disease.
1996 Jun
Terbinafine-induced prolonged cholestasis with reduction of interlobular bile ducts.
1997 Jul
Comparative study of antifungal activity of sertaconazole, terbinafine, and bifonazole against clinical isolates of Candida spp., Cryptococcus neoformans and dermatophytes.
1997 Nov-Dec
Safety of oral terbinafine: results of a postmarketing surveillance study in 25,884 patients.
1997 Oct
In vitro activities of terbinafine against cutaneous isolates of Candida albicans and other pathogenic yeasts.
1998 May
Ergosterol biosynthesis inhibitors become fungicidal when combined with calcineurin inhibitors against Candida albicans, Candida glabrata, and Candida krusei.
2003 Mar
Terbinafine resistance in a pleiotropic yeast mutant is caused by a single point mutation in the ERG1 gene.
2003 Sep 26
[Antimycotics suppress interleukin-4 and interleukin-5 production in anti-CD3 plus anti-CD28-stimulated T cells from patients with atopic dermatitis].
2004
Ursodeoxycholic acid for terbinafine-induced toxic hepatitis.
2004 Jun
[Colestasic toxic hepatitis caused by terbinafine: case report].
2004 Oct-Dec
Safety and tolerability of oral antifungal agents in the treatment of fungal nail disease: a proven reality.
2005 Dec
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Terbinafine inhibits endothelial cell migration through suppression of the Rho-mediated pathway.
2006 Dec
Comparable efficacy and safety of various topical formulations of terbinafine in tinea pedis irrespective of the treatment regimen: results of a meta-analysis.
2007
Terbinafine-induced hepatic failure requiring liver transplantation.
2007 Jan
Terbinafine-induced acute autoimmune hepatitis in the setting of hepatitis B virus infection.
2007 May
N- and S-alpha-l-arabinopyranosyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles. First synthesis and biological evaluation.
2007 Sep
Terbinafine-induced acute generalized exanthematous pustulosis.
2008 Apr
Synthesis of new N-phenylpyrazole derivatives with potent antimicrobial activity.
2008 Apr 15
Terbinafine hydrochloride oral granules versus oral griseofulvin suspension in children with tinea capitis: results of two randomized, investigator-blinded, multicenter, international, controlled trials.
2008 Jul
Synthesis and SAR studies of biaryloxy-substituted triazoles as antifungal agents.
2008 Jun 1
Antifungal triterpene glycosides from the sea cucumber Bohadschia marmorata.
2009 Feb
Terbinafine: a pharmacological and clinical review.
2009 Nov
Fungicide activity of 5-(4-chlorobenzylidene)-(Z)-2-dimethylamino-1,3-thiazol-4-one against Cryptococcus neoformans.
2010 Jan
Update on antifungal therapy with terbinafine.
2010 Jun
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
Isavuconazole: a comprehensive review of spectrum of activity of a new triazole.
2010 Nov
Terbinafine stimulates the pro-inflammatory responses in human monocytic THP-1 cells through an ERK signaling pathway.
2010 Oct 23
Development of a highly sensitive cytotoxicity assay system for CYP3A4-mediated metabolic activation.
2011 Aug
Synthesis and in-vitro antimicrobial activity of secondary and tertiary amines containing 2-chloro-6-methylquinoline moiety.
2011 Jul
In vitro antifungal susceptibility of clinically relevant species belonging to Aspergillus section Flavi.
2013 Apr
Assessment of phytochemicals, antimicrobial and cytotoxic activities of extract and fractions from Fagonia olivieri (Zygophyllaceae).
2013 Jul 10
Hippolachnin A, a new antifungal polyketide from the South China Sea sponge Hippospongia lachne.
2013 Jul 19
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.
2014
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 Jan
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 Mar 3
Identification and antifungal susceptibility of fungi isolated from dermatomycoses.
2014 May
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
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
A metoprolol-terbinafine combination induced bradycardia.
2015 Sep
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 Sat Jun 26 14:06:27 UTC 2021
Edited
by admin
on Sat Jun 26 14:06:27 UTC 2021
Record UNII
G7RIW8S0XP
Record Status Validated (UNII)
Record Version
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Name Type Language
TERBINAFINE
INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official 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
LAMASIL
Brand Name English
TERBINAFINE [WHO-DD]
Common Name English
SF 86-327
Code English
TERBINAFINE COMPONENT OF OSURNIA
Brand Name 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
TDT-067
Code English
Classification Tree Code System Code
NDF-RT N0000175874
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 13.1
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
WHO-ATC D01BA02
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
LIVERTOX 937
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
EMA VETERINARY ASSESSMENT REPORTS OSURNIA [AUTHORIZED]
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
WHO-VATC QD01AE15
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
NDF-RT N0000007522
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
NDF-RT N0000007522
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
NCI_THESAURUS C514
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
CFR 21 CFR 524.957
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
CFR 21 CFR 524.955
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
WHO-ATC D01AE15
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
WHO-VATC QD01BA02
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
Code System Code Type Description
EPA CompTox
91161-71-6
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
DRUG CENTRAL
2597
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
EVMPD
SUB10909MIG
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
ChEMBL
CHEMBL822
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
RXCUI
37801
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY RxNorm
LACTMED
Terbinafine
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
MERCK INDEX
M10569
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
TERBINAFINE
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
NCI_THESAURUS
C48019
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
INN
5657
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
DRUG BANK
DB00857
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
CAS
91161-71-6
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
PUBCHEM
1549008
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
FDA UNII
G7RIW8S0XP
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
MESH
C041359
Created by admin on Sat Jun 26 14:06:28 UTC 2021 , Edited by admin on Sat Jun 26 14:06:28 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INHIBITOR
POTENT
METABOLIC ENZYME -> SUBSTRATE
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ACTIVE MOIETY