Terbinafine

Summary

Terbinafine (CHEMBL822) is an approved small-molecule EC 1.14.13.132 (squalene monooxygenase) inhibitor (ATC D01AE15); indicated across 7 conditions including tinea infection and tinea unguium.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: D01AE15 (+1 more)
• Indications: 7 conditions
• Clinical trials: 37
• Chemistry: 291.4 Da · C21H25N

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL822
Name	Terbinafine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	1549008
ChEBI	CHEBI:9448
ATC	D01AE15, D01BA02
Molecular formula	C21H25N
Molecular weight	291.4
InChIKey	DOMXUEMWDBAQBQ-WEVVVXLNSA-N

SMILES: CC(C)(C)C#C/C=C/CN(C)CC1=CC=CC2=CC=CC=C21

IUPAC name: (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine

ChEBI definition: A tertiary amine that is N-methyl-1-naphthalenemethylamine in which the amino hydrogen is replaced by a 3-(tertbutylethynyl)allyl group. An antifungal agent administered orally (generally as the hydrochloride salt) for the treatment of skin and nail infections.

Pharmacological roles (ChEBI): EC 1.14.13.132 (squalene monooxygenase) inhibitor, P450 inhibitor, sterol biosynthesis inhibitor.

Also known as: Lamasil, Lamisil, Lamisil at, TDT-067, Terbinafina, Terbinafine, Terbinafine component of osurnia, terbinafine, Terbinafin, SID26754460, SID29215261, TERBINAFINE

Parent form; salt/anhydrous children: CHEMBL1200832

Patent coverage: 9,823 distinct patent families (33,025 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 32,400 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: Nuclear receptor ROR-gamma, Prelamin-A/C, Alpha-2A adrenergic receptor, Sodium-dependent noradrenaline transporter, Sigma non-opioid intracellular receptor 1, Cytochrome P450 2D6, Squalene monooxygenase, Squalene monooxygenase.

Bioactivity

ChEMBL activities: 10 potent at pChembl ≥ 5 of 12 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
LMNA	7.8	Potency	15.8	nM	CHEMBL_ACT_3642694
SQLE	7.52	Ki	30	nM	CHEMBL_ACT_1244509
CYP2D6	6.7	IC50	200	nM	CHEMBL_ACT_7806143
SIGMAR1	6.63	Ki	235.4	nM	CHEMBL_ACT_7808304
SIGMAR1	6.25	IC50	560.2	nM	CHEMBL_ACT_7808303
ADRA2A	5.67	Ki	2139	nM	CHEMBL_ACT_7804058
SLC6A2	5.39	Ki	4095	nM	CHEMBL_ACT_7804070
SLC6A2	5.38	IC50	4130	nM	CHEMBL_ACT_7804069
ADRA2A	5.24	IC50	5703	nM	CHEMBL_ACT_7804057
SQLE	5.22	IC50	6000	nM	CHEMBL_ACT_1244510

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

2 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
tinea infection	4	MONDO:0005982	EFO:0007510
tinea unguium	4	MONDO:0001628	MONDO:0001628

5 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
tinea pedis	3	MONDO:0005984	EFO:0007512
ulcerative colitis	2	MONDO:0005101	EFO:0000729
Crohn disease	2	MONDO:0005011	EFO:0000384
fungal infectious disease	1	MONDO:0002041	MONDO:0002041
chronic hepatitis B virus infection	1	MONDO:0005366	EFO:0004239

Clinical trials

Total trials: 37.

Phase distribution

Phase	Trials
PHASE2	9
PHASE3	8
PHASE1	8
Not specified	8
PHASE4	1
PHASE2/PHASE3	1
PHASE1/PHASE2	1
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01851590	PHASE4	COMPLETED	Resin vs. Amorolfine vs. Terbinafine Treatment in Onychomycosis
NCT00117754	PHASE3	COMPLETED	Terbinafine Compared to Griseofulvin in Children With Tinea Capitis
NCT00117767	PHASE3	COMPLETED	Terbinafine Compared to Griseofulvin in Children With Tinea Capitis
NCT00443820	PHASE3	COMPLETED	Efficacy Safety, and Tolerability of Topical Terbinafine in Patients With Mild to Moderate Toenail Fungus of the Big Toenail
NCT00443898	PHASE3	COMPLETED	Efficacy, Safety, and Tolerability of Topical Terbinafine in Patients With Mild to Moderate Toenail Fungus of the Big Toenail
NCT01433107	PHASE3	COMPLETED	Efficacy and Safety of Terbinafine Film Forming Solution in Patients With Tinea Pedis
NCT03171584	PHASE3	UNKNOWN	Antifungal Drugs in Treatment of Onychomycosis
NCT04880980	PHASE3	COMPLETED	Comparison of Efficacy of Double Dose Oral Terbinafine Vs Itraconazole in Treatment of Dermatophyte Infections of Skin.
NCT05128916	PHASE3	UNKNOWN	Efficacy of Intralesional PRP in Treatment of Onychomycosis
NCT05881980	PHASE2/PHASE3	UNKNOWN	Efficacy and Safety of Terbinafine and Itraconazole
NCT06295328	PHASE1/PHASE2	RECRUITING	From Fungus to Virus, Investigating the Safety and Efficacy of Terbinafine in Chronic Hepatitis B Patients
NCT07365423	PHASE2	RECRUITING	Terbinafine for Biochemically Recurrent Prostate Cancer (TerbinaPro)
NCT07382427	PHASE2	NOT_YET_RECRUITING	A Phase 2 Study to Assess the Effectiveness of Topical Terbinafine in Participants With Mild to Moderate Onychomycosis of the Toenails
NCT00491764	PHASE2	COMPLETED	A Study to Evaluate Efficacy and Safety of Four Posaconazole Regimens With Placebo and Terbinafine in the Treatment of Toenail Onychomycosis (Study P05082AM2)(COMPLETED)
NCT01080079	PHASE2	COMPLETED	Efficacy and Safety Study of Iontophoretic Application of Terbinafine Gel in Subjects With Onychomycosis
NCT01790165	PHASE2	COMPLETED	TDT 067 Open Label Multi-Dose Onychomycosis Study
NCT02606032	PHASE2	COMPLETED	Trial of Antimicrobials Versus Placebo in Addition to Fecal Transplant Therapy in Ulcerative Colitis
NCT03135912	PHASE2	COMPLETED	Three-Arm Trial of Novel Treatment for Tinea Pedis
NCT03471455	PHASE2	UNKNOWN	Isotretinoin In Preventing Recurrences In Chronic Recurrent Dermatophytosis
NCT03999437	PHASE2	UNKNOWN	SINGLE-APPLICATION TERBINAFINE HYDROCHLORIDE (1%) TOPICAL LIQUID SOLUTION VERSUS A SINGLE-APPLICATION BUTENAFINE HYDROCHLORIDE (1%) TOPICAL LIQUID SOLUTION FOR THE TREATMENT OF TINEA PEDIS
NCT06400056	PHASE1	NOT_YET_RECRUITING	Clinical and Laboratory Evaluation of Antifungal Resistance in Tinea Capitis
NCT00647647	PHASE1	COMPLETED	Fasting Study of Terbinafine Hydrochloride Tablets 250 mg and Lamisil® Tablets 250 mg
NCT00648713	PHASE1	COMPLETED	Fed Study of Terbinafine Hydrochloride Tablets 250 mg and Lamisil® 250 mg
NCT00691184	PHASE1	COMPLETED	Safety and Pharmacokinetics of Terbinafine Hydrogen Chloride (HCl) Nail Lacquer in Patients With Onychomycosis
NCT01286688	PHASE1	COMPLETED	Bioequivalence Study of Terbinafine Hydrochloride Tablets, 250 mg of Dr. Reddy’s Under Fasting Conditions
NCT01286701	PHASE1	COMPLETED	Bioequivalence Study of Terbinafine Hydrochloride Tablets, 250 mg of Dr. Reddy’s Under Fed Conditions
NCT01772212	PHASE1	COMPLETED	Bioequivalence Study for Terbinafine 250 mg
NCT05578950	PHASE1	COMPLETED	Comparative Study Between Pulse Therapy With Oral Itraconazole Versus Continuous Oral Terbinafine Therapy for Treatment of Onychomycosis
NCT05119712	EARLY_PHASE1	WITHDRAWN	Terbinafine Treatment of Axial Spondyloarthropathy
NCT05482763	Not specified	ACTIVE_NOT_RECRUITING	Mycosis Culture Collection From Dermatological Isolated
NCT07046988	Not specified	RECRUITING	Population Pharmacokinetics of Terbinafine in Children With Tinea Capitis
NCT07152327	Not specified	NOT_YET_RECRUITING	Terbinafine Hydrochloride for the Treatment of Otomycosis
NCT07242703	Not specified	NOT_YET_RECRUITING	Efficacy of Ultraviolet B Phototherapy in the Management of Resistant and Relapsing Tinea Corporis and Tinea Cruris
NCT00002394	Not specified	COMPLETED	Safety and Effectiveness of Giving Lamisil to HIV-Positive Subjects With Thrush Who Have Not Responded to Fluconazole Treatment
NCT00602251	Not specified	COMPLETED	Bioequivalency Study of Terbinafine Tablets Under Fed Conditions
NCT00602342	Not specified	COMPLETED	Bioequivalency Study of Terbinafine Tablets Under Fasting Conditions
NCT07068256	Not specified	COMPLETED	Efficacy Comparison of Itraconazole Pulse Therapy and Terbinafine Therapy in Treatment of Tinea Capitis in Children.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).