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

Details

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

SHOW SMILES / InChI
Structure of TERBINAFINE

SMILES

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

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
115
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 30.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
LAMISIL

Approved Use

Uses cures most athlete’s foot (tinea pedis) between the toes.Effectiveness on the bottom or sides of foot is unknown. cures most jock itch (tinea cruris) and ringworm (tinea corporis) relieves itching, burning, cracking and scaling which accompany these conditions

Launch Date

8.9380802E11
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
1737
substrate
1037
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1054

CYP2C8
693

CYP2C19
991

CYP2B6
664
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
1891
 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
1054
 yes
CYP1A2
1054
 yes
Hydroxyterbinafine
4
CYP2B6
664
 yes
Hydroxyterbinafine
4
CYP2C19
991
 yes
CYP2C19
991
 yes
Hydroxyterbinafine
4
CYP2C8
693
 yes
CYP2C8
693
 yes
Hydroxyterbinafine
4
CYP2C9
1037
 yes
Hydroxyterbinafine
4
CYP3A4
1737
 yes
Hydroxyterbinafine
4
CYP2C9
1037
 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
1737
 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
1647
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
Antifungal activity of the allylamine derivative terbinafine in vitro.
1987 Sep
Terbinafine-induced cholestatic liver disease.
1996 Jun
Randomized double-blind comparison of short-term itraconazole and terbinafine therapy for toenail onychomycosis.
1999 May
Synergy between 6-amino-2-n-pentylthiobenzothiazole and ergosterol biosynthesis-inhibiting antimycotics against Candida albicans in vitro.
2000 Jul
Synergistic interaction of terbinafine with triazoles or amphotericin B against Aspergillus species.
2001 Feb
In vitro activities of terbinafine against Aspergillus species in comparison with those of itraconazole and amphotericin B.
2001 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
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
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
Terbinafine: a pharmacological and clinical review.
2009 Nov
Isavuconazole: a comprehensive review of spectrum of activity of a new triazole.
2010 Nov
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
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

Patents

JP2001354591A
7
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122
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8
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4
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4
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4
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JP2003055205A
4
JP2003514875A
13
JP2004035411A
6
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JP2004203895A
4
JP2005036000A
4
JP2005104915A
6
JP2005104916A
4
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4
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8
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4
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4
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4
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4
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60
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4
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4
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4
JP2007503428A
35
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7
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4
JP2007527852A
15
JP2008132349A
4
JP2008280351A
4
JP2009007265A
4
JP2009102310A
4
JP2009526755A
447
JP2010006709A
4
JP2010126532A
4
JP2010189440A
4
JP2010507658A
34
JP2011132247A
4
JP2011526302A
67
JP4722295B2
104
JP4728220B2
15
JP4733129B2
5
JP4763957B2
87
JP4787165B2
101
JP4806162B2
16
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
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
Terbinafine [WHO-DD]
Common Name English
TDT-067
Code English
Classification Tree Code System Code
NDF-RT N0000175874
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 13.1
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
WHO-ATC D01BA02
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
LIVERTOX NBK548617
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS OSURNIA [AUTHORIZED]
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
WHO-VATC QD01AE15
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
NDF-RT N0000007522
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
NDF-RT N0000007522
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
CFR 21 CFR 524.957
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
CFR 21 CFR 524.955
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
WHO-ATC D01AE15
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
WHO-VATC QD01BA02
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
Code System Code Type Description
USAN
Z-4
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID2023640
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
DRUG CENTRAL
2597
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
EVMPD
SUB10909MIG
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
ChEMBL
CHEMBL822
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
RXCUI
37801
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY RxNorm
LACTMED
Terbinafine
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
SMS_ID
100000092310
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
MERCK INDEX
m10569
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
TERBINAFINE
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
NCI_THESAURUS
C48019
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
INN
5657
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
DRUG BANK
DB00857
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
CAS
91161-71-6
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
PUBCHEM
1549008
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
FDA UNII
G7RIW8S0XP
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
CHEBI
9448
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
MESH
C041359
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
DAILYMED
G7RIW8S0XP
Created by admin on Fri Dec 15 15:54:39 UTC 2023 , Edited by admin on Fri Dec 15 15:54:39 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of TERBINAFINE
SALT/SOLVATE (PARENT)
Structure of TERBINAFINE HYDROCHLORIDE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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