You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:12 UTC
HMDB IDHMDB0015223
Secondary Accession Numbers
  • HMDB15223
Metabolite Identification
Common NameButenafine
DescriptionButenafine, also known as mentax, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Butenafine is a drug which is used for the topical treatment of the following dermatologic infections: tinea (pityriasis) versicolor due to m. furfur, interdigital tinea pedis (athlete’s foot), tinea corporis (ringworm) and tinea cruris (jock itch) due to e. floccosum, t. mentagrophytes, t. rubrum, and t. tonsurans. Butenafine is a very strong basic compound (based on its pKa). Butenafine is a potentially toxic compound. When a high concentration of squalene is reached, it is thought to have an effect of directly kill fungal cells. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Blockage of squalene monooxygenase also leads to a subsequent accumulation of squalene. Butenafine's mechanism of action is believed to involve the synthesis inhibition of sterols. Although the mechanism of action has not been fully established, it has been suggested that butenafine, like allylamines, interferes with sterol biosynthesis (especially ergosterol) by inhibiting squalene monooxygenase, an enzyme responsible for converting squalene to 2,3-oxydo squalene. Butenafine is mainly active against dermatophytes and has superior fungicidal activity against this group of fungi when compared to that of terbinafine, naftifine, tolnaftate, clotrimazole, and bifonazole. Butenafine is a synthetic antifungal agent that is structurally and pharmacologically related to allylamine antifungals.
Structure
Data?1582753272
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 Weight317.4672
Monoisotopic Molecular Weight317.214349869
IUPAC Name[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Traditional Namebutenafine
CAS Registry Number101828-21-1
SMILES
CN(CC1=CC=C(C=C1)C(C)(C)C)CC1=CC=CC2=CC=CC=C12
InChI Identifier
InChI=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
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.6e-05 g/LNot Available
LogP6.6Not 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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-2912000000-2c89ed2a27ca719c5093Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-b991404e4a3bc6aadefaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0119000000-bd784f9c30b34fb0dc15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdp-1911000000-a9cab6ed25fa0c536850Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-afff1eba5ff5f66f1a8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0109000000-3229d502a37a8f211314Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bc-0922000000-601177d74a3082e00493Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01091 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01091 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01091
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2390
KEGG Compound IDC08067
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButenafine
METLIN IDNot Available
PubChem Compound2484
PDB IDNot Available
ChEBI ID3238
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Iwatani W, Arika T, Yamaguchi H: Two mechanisms of butenafine action in Candida albicans. Antimicrob Agents Chemother. 1993 Apr;37(4):785-8. [PubMed:8494375 ]
  2. McNeely W, Spencer CM: Butenafine. Drugs. 1998 Mar;55(3):405-12; discussion 413. [PubMed:9530545 ]
  3. 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. [PubMed:9646136 ]
  4. Syed TA, Maibach HI: Butenafine hydrochloride: for the treatment of interdigital tinea pedis. Expert Opin Pharmacother. 2000 Mar;1(3):467-73. [PubMed:11249531 ]
  5. 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. [PubMed:11709307 ]
  6. Gupta AK: Butenafine: an update of its use in superficial mycoses. Skin Therapy Lett. 2002 Sep;7(7):1-2, 5. [PubMed:12432425 ]
  7. 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 . [PubMed:18624686 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name:
SQLE
Uniprot ID:
Q14534
Molecular weight:
63922.505
References
  1. Mukherjee PK, Leidich SD, Isham N, Leitner I, Ryder NS, Ghannoum MA: Clinical Trichophyton rubrum strain exhibiting primary resistance to terbinafine. Antimicrob Agents Chemother. 2003 Jan;47(1):82-6. [PubMed:12499173 ]
  2. Gao PH, Cao YB, Xu Z, Zhang JD, Zhang WN, Wang Y, Gu J, Cao YY, Li RY, Jia XM, Jiang YY: In vitro antifungal activity of ZJ-522, a new triazole restructured from fluconazole and butenafine, against clinically important fungi in comparison with fluconazole and butenafine. Biol Pharm Bull. 2005 Aug;28(8):1414-7. [PubMed:16079485 ]
  3. 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 . [PubMed:18624686 ]
  4. Ramam M, Prasad HR, Manchanda Y, Khaitan BK, Banerjee U, Mukhopadhyaya A, Shetty R, Gogtay JA: Randomised controlled trial of topical butenafine in tinea cruris and tinea corporis. Indian J Dermatol Venereol Leprol. 2003 Mar-Apr;69(2):154-8. [PubMed:17642865 ]
  5. Iwatani W, Arika T, Yamaguchi H: Two mechanisms of butenafine action in Candida albicans. Antimicrob Agents Chemother. 1993 Apr;37(4):785-8. [PubMed:8494375 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]