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

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

Description

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

Sandoz-Forschungsinstitut
4
Sources: Proc. Int. Congr. Chemother., 13th (1983), 6, 116/47-116/51.

Approval Year

1992
62
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7701
 30.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
7997
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

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:
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

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:
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1470
substrate
865
inhibitor
1421
inhibitor
1360

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
892

CYP2C8
586

CYP2C19
830

CYP2B6
575
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
1455
 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
CYP1A2
892
 yes
CYP1A2
892
 yes
Hydroxyterbinafine
4
CYP2B6
575
 yes
Hydroxyterbinafine
4
CYP2C19
830
 yes
CYP2C19
830
 yes
Hydroxyterbinafine
4
CYP2C8
586
 yes
CYP2C8
586
 yes
Hydroxyterbinafine
4
CYP2C9
865
 yes
Hydroxyterbinafine
4
CYP3A4
1470
 yes
Hydroxyterbinafine
4
CYP2C9
865
 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: -
CYP3A4
1470
 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
hERG
1392
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

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
Effects of naftifine and terbinafine, two allylamine antifungal drugs, on selected functions of human polymorphonuclear leukocytes.
1994 Nov
Safety of oral terbinafine: results of a postmarketing surveillance study in 25,884 patients.
1997 Oct
Effects of sterol inhibitors on the ATP content of Pneumocystis carinii.
1999 Sep-Oct
An evaluation of the in vitro activity of terbinafine.
2000 Apr
Synergy between 6-amino-2-n-pentylthiobenzothiazole and ergosterol biosynthesis-inhibiting antimycotics against Candida albicans in vitro.
2000 Jul
Potent synergism of the combination of fluconazole and cyclosporine in Candida albicans.
2000 Sep
Use of terbinafine in mouse and rat models of Pneumocystis carinii pneumonia.
2002 Feb
[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
N- and S-alpha-l-arabinopyranosyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles. First synthesis and biological evaluation.
2007 Sep
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
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
Synthesis and in-vitro antimicrobial activity of secondary and tertiary amines containing 2-chloro-6-methylquinoline moiety.
2011 Jul
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
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
A metoprolol-terbinafine combination induced bradycardia.
2015 Sep
Patents

Patents

JP2001354591A
7
JP2001500477A
110
JP2001520188A
8
JP2002053462A
4
JP2002068974A
4
JP2002068975A
4
JP2002308835A
4
JP2002523372A
15
JP2002537317A
85
JP2003055205A
4
JP2003514875A
14
JP2004035411A
6
JP2004149508A
12
JP2004203895A
4
JP2005036000A
4
JP2005104915A
6
JP2005104916A
4
JP2005187339A
4
JP2005523252A
8
JP2006182733A
4
JP2006232853A
4
JP2006232854A
4
JP2006257068A
4
JP2006514917A
59
JP2006520800A
4
JP2007008893A
4
JP2007091643A
4
JP2007503428A
36
JP2007508287A
7
JP2007510712A
4
JP2007527852A
13
JP2008132349A
4
JP2008280351A
4
JP2009007265A
4
JP2009102310A
4
JP2009526755A
420
JP2010006709A
4
JP2010126532A
4
JP2010189440A
4
JP2010507658A
28
JP2011132247A
4
JP2011526302A
65
JP4722295B2
87
JP4728220B2
15
JP4733129B2
5
JP4763957B2
80
JP4787165B2
92
JP4806162B2
15
JPH00338521A
6
JPH00338522A
7
JPH01311025A
6

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.
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
ACTIVE MOIETY
Structure of TERBINAFINE
SALT/SOLVATE (PARENT)
Structure of TERBINAFINE HYDROCHLORIDE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
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