Butenafine

Summary

Butenafine (CHEMBL990) is an approved small-molecule EC 1.14.13.132 (squalene monooxygenase) inhibitor (ATC D01AE23); indicated across 1 condition including tinea pedis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: D01AE23
• Indications: 1 condition
• Clinical trials: 7
• Chemistry: 317.5 Da · C23H27N

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL990
Name	Butenafine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	2484
ChEBI	CHEBI:3238
ATC	D01AE23
Molecular formula	C23H27N
Molecular weight	317.5
InChIKey	ABJKWBDEJIDSJZ-UHFFFAOYSA-N

SMILES: CC(C)(C)C1=CC=C(C=C1)CN(C)CC2=CC=CC3=CC=CC=C32

IUPAC name: 1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine

ChEBI definition: Trimethylamine in which hydrogen atoms attached to different methyl groups are substituted by 1-naphthyl and 4-tert-butylphenyl groups. It is an inhibitor of squalene epoxidase, an enzyme responsible for the creation of sterols needed in fungal cell membranes, and is used as its hydrochloride salt for treatment of dermatological fungal infections.

Pharmacological roles (ChEBI): EC 1.14.13.132 (squalene monooxygenase) inhibitor, antifungal drug.

Also known as: Butenafina, Butenafine, SID29215487, volley, SID144205282, SID170465093, BUTENAFINE, Butenafine HCl, butenafine

Parent form; salt/anhydrous children: CHEMBL1200397

Patent coverage: 2,894 distinct patent families (10,505 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 10,270 (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: 10 (assay-derived). Sample: Prelamin-A/C, Alpha-2A adrenergic receptor, Acetylcholinesterase, Sodium-dependent noradrenaline transporter, 5-hydroxytryptamine receptor 2A, Sodium-dependent serotonin transporter, Voltage-gated inwardly rectifying potassium channel KCNH2, Sigma non-opioid intracellular receptor 1, Cytochrome P450 2D6, Nuclear receptor subfamily 1 group I member 2.

Bioactivity

ChEMBL activities: 11 potent at pChembl ≥ 5 of 14 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CYP2D6	6.52	IC50	300	nM	CHEMBL_ACT_7613997
SLC6A4	6.12	Ki	750	nM	CHEMBL_ACT_7615511
ADRA2A	5.86	Ki	1367	nM	CHEMBL_ACT_7612588
SLC6A4	5.85	IC50	1412	nM	CHEMBL_ACT_7615510
SIGMAR1	5.78	Ki	1662	nM	CHEMBL_ACT_7615513
KCNH2	5.55	AC50	2800	nM	CHEMBL_ACT_25117303
ADRA2A	5.44	IC50	3644	nM	CHEMBL_ACT_7612587
SLC6A2	5.41	IC50	3910	nM	CHEMBL_ACT_7612599
SLC6A2	5.41	Ki	3878	nM	CHEMBL_ACT_7612600
SIGMAR1	5.4	IC50	3953	nM	CHEMBL_ACT_7615512
ACHE	5.16	IC50	6907	nM	CHEMBL_ACT_7612571

Target pathways

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

Indications & clinical

Indications

1 indication (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
tinea pedis	1	MONDO:0005984	EFO:0007512

Clinical trials

Total trials: 7.

Phase distribution

Phase	Trials
PHASE3	4
PHASE1	2
PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT04531527	PHASE3	COMPLETED	Study to Learn More About the Potential of Antifungal Cream V61-044 Containing Trolamine to Cause Irritant Reaction of the Skin to Ultra Violet Light in Healthy Human Subjects
NCT04531540	PHASE3	COMPLETED	Study to Determine Skin Irritation and/or Sensitization Potential of an Antifungal Cream Containing Trolamine (Repeated Insult Patch Test)
NCT04531813	PHASE3	COMPLETED	Study to Determine Skin Irritation Potential of an Antifungal Cream Containing Trolamine After Repeated Skin Application (Cumulative Irritation Patch Test)
NCT04532164	PHASE3	COMPLETED	Study to Find Out if Cream V61-044 Used to Treat Fungal Infections Causes an Allergic Skin Reaction to Sunlight in Healthy Participants
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
NCT01119742	PHASE1	TERMINATED	Clinical Equivalence of Two Generic Butenafine Hydrochloride 1% Creams as Compared to Lotrimin Ultra Cream in Patients With Interdigital Tinea Pedis
NCT01580878	PHASE1	COMPLETED	Evaluate the Safety & Bioequivalence of a Generic Butenafine Cream & Lotrimin Ultra® & Compare Both to a Vehicle Control in Treatment of Interdigital Tinea Pedis

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

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