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Showing drug card for Butenafine (DB01091)

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Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:24
Primary Accession Number DB01091
Secondary Accession Number
  • APRD00833
Name Butenafine
Drug Type
  • Approved
  • Small Molecule
Description Butenafine hydrochloride is a synthetic benzylamine antifungal agent. Butenafine works by inhibiting the synthesis of ergosterol by inhibiting squalene epoxidase, an enzyme responsible for the creation of sterols needed in fungal cell membranes.
Synonyms
  1. Butenafina [INN-Spanish]
  2. Butenafine HCL
  3. Butenafine [INN]
  4. Butenafine hydrochloride
  5. Butenafinum [INN-Latin]
Brand Names
  1. Lotrimin Ultra
  2. Mentax
  3. Mentax-tc
Brand Mixtures Not Available
Chemical IUPAC Name 1-(4-tert-butylphenyl)-N-methyl-N-(naphthalen-1-ylmethyl)methanamine
Chemical Formula C23H27N
Chemical Structure Structure
CAS Registry Number 101828-21-1
InChI Identifier InChI=1/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 Key ABJKWBDEJIDSJZ-UHFFFAOYAT
KEGG Drug Not Available
KEGG Compound C08067 Link Image
PubChem Compound 2484 Link Image
PubChem Substance 10267 Link Image
ChEBI ID Not Available
PharmGKB ID PA448698 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02231063 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/butenafine.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Butenafine Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 317.4672
Monoisotopic Molecular Weight 317.2143
State Solid
Melting Point Not Available
Experimental Water Solubility Slightly soluble (HCl salt) Source: PhysProp
Predicted Water Solubility 7.56e-05 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 6.6 Source: PhysProp
Predicted LogP 5.86 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -6.62 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN(CC1=CC=C(C=C1)C(C)(C)C)CC1=CC=CC2=CC=CC=C12
Canonical SMILES CN(CC1=CC=C(C=C1)C(C)(C)C)CC1=CC=CC2=CC=CC=C12
Drug Category
  • Antifungal Agents
ATC Codes
AHFS Codes Not Available
Indication 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.
Pharmacology Butenafine is an antifungal agent that acts by inhibiting squalene epoxidase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. It 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. It is active also against Candida albicans and this activity is superior to that of terbinafine and naftifine. Butenafine also generates low MICs for Cryptococcus neoformans and Aspergillus spp. as well.
Mechanism of Action Like allylamines, butenafine inhibits ergosterol biosynthesis by blocking squalene epoxidation. 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.
Absorption The total amount absorbed through the skin into the systemic circulation has not been quantified.
Toxicity Not Available
Protein Binding Not Available
Biotransformation The primary metabolite in urine was formed through hydroxylation at the terminal t-butyl side-chain.
Half Life Following topical application, a biphasic decline of plasma butenafine concentrations was observed with the half-lives estimated to be 35 hours initial and over 150 hours terminal.
Dosage Forms
Form Route
Cream Topical
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
Organisms Affected
  • Fungi
Targets
  1. Squalene monooxygenase
Drug Target 1 [top]
Target 1 ID 634
Target 1 Name Squalene monooxygenase
Target 1 Synonyms
  1. EC 1.14.99.7
  2. SE
  3. Squalene epoxidase
Target 1 Gene Name SQLE
Target 1 Protein Sequence >Squalene monooxygenase 
MWTFLGIATFTYFYKKFGDFITLANREVLLCVLVFLSLGLVLSYRCRHRNGGLLGRQRSG
SQFALFSDILSGLPFIGFFWAKSPPESENKEQLGARRRRKGTNISETSLIGTAACTSTSS
QNDPEVIIVGAGVLGSALVAVLSRDGRKVTVIERDLKEPDRIVGEFLQPGGYHVLKDLGL
GDTVEGLDAQVVNGYMIHDQESKSEVQIPYPLSENNQVQSGRAFHHGRFIMSLRKAAMAE
PNAKFIEGVVLQLLEEDDVVMGVQYKDKETGDIKELHAPLTVVADGLFSKFRKSLVSNKV
SVSSHFVGFLMKNAPQFKANHAELILANPSPVLIYRISSSETRVLVDIRGEMPRNLREYM
VEKIYPQIPDHLKEPFLEATDNSHLRSMLASFLPPSSVKKRGVLLLGDAYNMRHPLTGGG
MTVAFKDIKLWRKLLKGIPDLYDDAAIFEANKSFYWARKTSHSFVVNILAQALYELFSAT
DDSLHQLRKACFLYFKLGGECVAGPVGLLSVLSPNPLALIGHFFAVAIYAVYFCFKSEPW
ITKPRALLSSSAVLYKACSVIFPLIYSEMKYMVH
Target 1 Number of Residues 583
Target 1 Molecular Weight 63940
Target 1 Theoretical pI 9.12
Target 1 GO Classification
Function
catalytic activity
oxidoreductase activity
Process
physiological process
metabolism
cellular metabolism
generation of precursor metabolites and energy
electron transport
Component
Not Available
Target 1 General Function Coenzyme transport and metabolism
Target 1 Specific Function Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway
Target 1 Pathways
Name SMPDB Link KEGG Link
Biosynthesis of steroids map00100 Link Image
Terpenoid biosynthesis map00900 Link Image
Target 1 Reactions
  • squalene + AH2 + O2 = (S)-squalene-2,3-epoxide + A + H2O
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 20-40
  • 61-81
  • 123-143
  • 546-566
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 2443316 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q14534 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ERG1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Microsome
  • microsomal membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1725 bp 
ATGTGGACTTTTCTGGGCATTGCCACTTTCACCTATTTTTATAAGAAGTTCGGGGACTTC
ATCACTTTGGCCAACAGGGAGGTCCTGTTGTGCGTGCTGGTGTTCCTCTCGCTGGGCCTG
GTGCTCTCCTACCGCTGTCGCCACCGAAACGGGGGTCTCCTCGGGCGCCAGCGGAGCGGC
TCCCAGTTCGCCCTCTTCTCGGATATTCTCTCAGGCCTGCCTTTCATTGGCTTCTTCTGG
GCCAAATCCCCCCCTGAATCAGAAAATAAGGAGCAGCTCGGGGCCAGGAGGCGCAGAAAA
GGAACCAATATTTCAGAAACAAGCTTAATAGGAACAGCTGCCTGTACATCAACATCTTCT
CAGAATGACCCAGAAGTTATCATCGTGGGAGCTGGCGTGCTTGGCTCTGCTTTGGTAGCT
GTGCTTTCCAGAGATGGAAGAAAGGTGACAGTCATTGAGAGAGACTTAAAAGAGCCTGAC
AGAATAGTTGGAGAATTCCTGCAGCCGGGTGGTTATCATGTTCTCAAAGACCTTGGTCTT
GGAGATACAGTGGAAGGTCTTGATGCCCAGGTTGTAAATGGTTACATGATTCATGATCAG
GAAAGCAAATCAGAGGTTCAGATTCCTTACCCTCTGTCAGAAAACAATCAAGTGCAGAGT
GGAAGAGCTTTCCATCACGGAAGATTCATCATGAGTCTCCGGAAAGCAGCTATGGCAGAG
CCCAATGCAAAGTTTATTGAAGGTGTTGTGTTACAGTTATTAGAGGAAGATGATGTTGTG
ATGGGAGTTCAGTACAAGGATAAAGAGACTGGAGATATCAAGGAACTCCATGCTCCACTG
ACTGTTGTTGCAGATGGGCTTTTCTCCAAGTTCAGGAAAAGCCTGGTCTCCAATAAAGTT
TCTGTATCATCTCATTTTGTTGGCTTTCTTATGAAGAATGCACCACAGTTTAAAGCAAAT
CATGCTGAACTTATTTTAGCTAACCCGAGTCCAGTTCTCATCTACCGGATTTCATCCAGT
GAAACTCGAGTACTTGTTGACATTAGAGGAGAAATGCCAAGGAATTTAAGAGAATACATG
GTTGAAAAAATTTACCCACAAATACCTGATCACCTGAAAGAACCATTCTTAGAAGCCACT
GACAATTCTCATCTGAGGTCCATGCTAGCAAGCTTCCTTCCTCCTTCATCAGTGAAGAAA
CGAGGTGTTCTTCTTTTGGGAGACGCATATAATATGAGGCATCCACTTACTGGTGGAGGA
ATGACTGTTGCTTTTAAAGATATAAAACTATGGAGAAAACTGCTAAAGGGTATCCCTGAC
CTTTATGATGATGCAGCTATTTTCGAGGCCAACAAATCATTTTACTGGGCAAGAAAAACA
TCTCATTCCTTTGTCGTGAATATCCTTGCTCAGGCTCTTTATGAATTATTTTCTGCCACA
GATGATTCCCTGCATCAACTAAGAAAAGCCTGTTTTCTTTATTTCAAACTTGGTGGCGAA
TGTGTTGCGGGTCCTGTTGGGCTGCTTTCTGTATTGTCTCCTAACCCTCTAGCTTTAATT
GGACACTTCTTTGCTGTTGCAATCTATGCCGTGTATTTTTGCTTTAAGTCAGAACCTTGG
ATTACAAAACCTCGAGCCCTTCTCAGTAGTAGTGCTGTATTGTACAAAGCGTGTTCTGTA
ATATTTCCTCTAATTTACTCAGAAATGAAGTATATGGTTCATTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID SQLE Link Image
Target 1 GenAtlas ID SQLE Link Image
Target 1 HGNC ID HGNC:11279 Link Image
Target 1 Chromosome Location 8
Target 1 Locus 8q24.1
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Nakamura Y, Sakakibara J, Izumi T, Shibata A, Ono T: Transcriptional regulation of squalene epoxidase by sterols and inhibitors in HeLa cells. J Biol Chem. 1996 Apr 5;271(14):8053-6. [PubMed Link Image]
  2. Nagai M, Sakakibara J, Wakui K, Fukushima Y, Igarashi S, Tsuji S, Arakawa M, Ono T: Localization of the squalene epoxidase gene (SQLE) to human chromosome region 8q24.1. Genomics. 1997 Aug 15;44(1):141-3. [PubMed Link Image]
Target 1 Drug 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 Link Image]
  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 Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.