Butenafine (CED0011633)

Record Information
Version1.0
Creation Date2016-05-22 04:28:02 UTC
Update Date2026-08-22 00:58:07 UTC
Accession NumberCHEM017566
Identification
Common NameButenafine
ClassSmall Molecule
Description
Butenafine belongs to the naphthalenes, a class of benzenoids within the organic compounds. This compound has the chemical formula C23H27N and an average molecular weight of 317.47 g/mol. In terms of biological activity, it acts as an inhibitor or modulator of squalene monooxygenase (SQLE) and targets squalene epoxidase ERG1. The compound is associated with 11 recorded sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is used as an antifungal for dermatological use. In food and food processing applications, it is used for food preservation. Other recorded sources include household cleaning and consumer products, specifically tobacco smoke filters, perfumes within detergents and soaps, cigar cigarettes, and other smoking requisites. Additionally, it is found in electrical and electronic equipment, including electrodes, hybrid capacitors, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. The recorded route of exposure for this substance is topical.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(4-Tert-butyl-benzyl)-methyl-naphthalen-1-ylmethyl-amineChEBI
(4-Tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamineChEBI
4-Tert-butylbenzyl(methyl)(1-naphthalenemethyl)amineChEBI
ButenafinaChEBI
ButenafinumChEBI
N-(p-Tert-butylbenzyl)-N-methyl-1-naphthalenemethylamineChEBI
Butenafine hydrochlorideHMDB
N-4-Tert-butylbenzyl-N-methyl-1-naphthalene methylamine hydrochlorideHMDB
MentaxHMDB
Chemical FormulaC23H27N
Average Molecular Mass317.467 g/mol
Monoisotopic Mass317.214 g/mol
CAS Registry Number101828-21-1
IUPAC Name[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Traditional Namebutenafine
SMILESCN(CC1=CC=C(C=C1)C(C)(C)C)CC1=CC=CC2=CC=CC=C12
InChI IdentifierInChI=1S/C23H27N/c1-23(2,3)21-14-12-18(13-15-21)16-24(4)17-20-10-7-9-19-8-5-6-11-22(19)20/h5-15H,16-17H2,1-4H3
InChI KeyABJKWBDEJIDSJZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Phenylpropane
  • Phenylmethylamine
  • Benzylamine
  • Aralkylamine
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.6e-05 g/LALOGPS
logP5.85ALOGPS
logP6.17ChemAxon
logS-6.6ALOGPS
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity104.33 m³·mol⁻¹ChemAxon
Polarizability38.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-2912000000-2c89ed2a27ca719c5093Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-b991404e4a3bc6aadefaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0119000000-bd784f9c30b34fb0dc15Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fdp-1911000000-a9cab6ed25fa0c536850Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-afff1eba5ff5f66f1a8bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0109000000-3229d502a37a8f211314Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01bc-0922000000-601177d74a3082e00493Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-888fc78224dc3dd94257Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-1904000000-22d19910a589d522612cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-2900000000-716706abe01dbb1ea4ceNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-613644afd8812fe192d7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0209000000-4f4c585a2889c3a6c620Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ou-0912000000-25b0266ad68788222f6bNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
947.0Log mg/kg[530:1700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
299Antifungals for dermatological useHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)18.5281
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)14.9471
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)20.3186
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)48.4222
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)42.8949
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)69.4415
Interferon alpha/beta receptor 1 structureClick to view 3D structureInterferon alpha/beta receptor 1P17181HumansPredicted (SEA)1.71268
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)207.468
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)288.976
Click to view 3D structureSqualene epoxidase ERG1Q92206YeastPredicted (SEA)0.389246
Click to view 3D structureAmine oxidase [flavin-containing] BP19643Rattus norvegicusPredicted (SEA)70.9206
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)259.238
Listeriolysin regulatory protein structureClick to view 3D structureListeriolysin regulatory proteinP22262Listeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)Predicted (SEA)1.24559
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)308.361
Click to view 3D structure4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming)Q2FDU6Staphylococcus aureus (strain USA300)Predicted (SEA)2.17978
Click to view 3D structureChaperone protein dnaKC3TRK2Escherichia coliPredicted (SEA)17.4382
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)520.889
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)525.171
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)510.068
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)593.99
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)402.247
Click to view 3D structureSigma non-opioid intracellular receptor 1Q9R0C9Rattus norvegicusPredicted (SEA)397.42
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)3087.58
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)1193.97
Click to view 3D structureAmine oxidase [flavin-containing] AP21396Rattus norvegicusPredicted (SEA)136.236
Concentrations
Not Available
External Links
DrugBank IDDB01091
HMDB IDHMDB0015223
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkButenafine
Chemspider ID2390
ChEBI ID3238
PubChem Compound ID2484
Kegg Compound IDC08067
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17371821
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8340915
3. Iwatani W, Arika T, Yamaguchi H: Two mechanisms of butenafine action in Candida albicans. Antimicrob Agents Chemother. 1993 Apr;37(4):785-8.
4. McNeely W, Spencer CM: Butenafine. Drugs. 1998 Mar;55(3):405-12; discussion 413.
5. Reyes BA, Beutner KR, Cullen SI, Rosen T, Shupack JL, Weinstein MB: Butenafine, a fungicidal benzylamine derivative, used once daily for the treatment of interdigital tinea pedis. Int J Dermatol. 1998 Jun;37(6):450-3.
6. Syed TA, Maibach HI: Butenafine hydrochloride: for the treatment of interdigital tinea pedis. Expert Opin Pharmacother. 2000 Mar;1(3):467-73.
7. Mingeot-Leclercq MP, Gallet X, Flore C, Van Bambeke F, Peuvot J, Brasseur R: Experimental and conformational analyses of interactions between butenafine and lipids. Antimicrob Agents Chemother. 2001 Dec;45(12):3347-54.
8. Gupta AK: Butenafine: an update of its use in superficial mycoses. Skin Therapy Lett. 2002 Sep;7(7):1-2, 5.
9. Singal A: Butenafine and superficial mycoses: current status. Expert Opin Drug Metab Toxicol. 2008 Jul;4(7):999-1005. doi: 10.1517/17425255.4.7.999 .