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101828-21-1 molecular structure
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[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine

ChemBase ID: 962
Molecular Formular: C23H27N
Molecular Mass: 317.46718
Monoisotopic Mass: 317.21434987
SMILES and InChIs

SMILES:
N(Cc1ccc(C(C)(C)C)cc1)(Cc1c2c(ccc1)cccc2)C
Canonical SMILES:
CN(Cc1cccc2c1cccc2)Cc1ccc(cc1)C(C)(C)C
InChI:
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
InChIKey:
ABJKWBDEJIDSJZ-UHFFFAOYSA-N

Cite this record

CBID:962 http://www.chembase.cn/molecule-962.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
IUPAC Traditional name
butenafine
Brand Name
Lotrimin Ultra
Mentax
Mentax-tc
Synonyms
Butenafina [INN-Spanish]
Butenafine HCL
Butenafine hydrochloride
Butenafine [INN]
Butenafinum [INN-Latin]
Butenafine
CAS Number
101828-21-1
PubChem SID
160964425
46506191
PubChem CID
2484

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB01091 external link
PubChem 2484 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 2.8725023  LogD (pH = 7.4) 4.343121 
Log P 6.173649  Molar Refractivity 104.3294 cm3
Polarizability 42.022823 Å3 Polar Surface Area 3.24 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 5.85  LOG S -6.62 
Solubility (Water) 7.56e-05 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Slightly soluble (HCl salt) expand Show data source
Hydrophobicity(logP)
6.6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01091 external link
Item Information
Drug Groups approved
Description Butenafine hydrochloride is a synthetic benzylamine antifungal agent. Butenafine works by inhibiting the synthesis of sterols by inhibiting squalene epoxidase, an enzyme responsible for the creation of sterols needed in fungal cell membranes.
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 a synthetic antifungal agent that is structurally and pharmacologically related to allylamine antifungals. The exact mechanism of action has not been established, but it is suggested that butenafine's antifungal activity is exerted through the alteration of cellular membranes, which results in increased membrane permeability, and growth inhibition. 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. It is also active 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.
Affected Organisms
Fungi
Biotransformation The primary metabolite in urine was formed through hydroxylation at the terminal t-butyl side-chain.
Absorption The total amount absorbed through the skin into the systemic circulation has not been quantified.
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.
References
McNeely W, Spencer CM: Butenafine. Drugs. 1998 Mar;55(3):405-12; discussion 413. [Pubmed]
Singal A: Butenafine and superficial mycoses: current status. Expert Opin Drug Metab Toxicol. 2008 Jul;4(7):999-1005. [Pubmed]
Gupta AK: Butenafine: an update of its use in superficial mycoses. Skin Therapy Lett. 2002 Sep;7(7):1-2, 5. [Pubmed]
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]
Syed TA, Maibach HI: Butenafine hydrochloride: for the treatment of interdigital tinea pedis. Expert Opin Pharmacother. 2000 Mar;1(3):467-73. [Pubmed]
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]
Iwatani W, Arika T, Yamaguchi H: Two mechanisms of butenafine action in Candida albicans. Antimicrob Agents Chemother. 1993 Apr;37(4):785-8. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • McNeely W, Spencer CM: Butenafine. Drugs. 1998 Mar;55(3):405-12; discussion 413. Pubmed
  • • Singal A: Butenafine and superficial mycoses: current status. Expert Opin Drug Metab Toxicol. 2008 Jul;4(7):999-1005. Pubmed
  • • Gupta AK: Butenafine: an update of its use in superficial mycoses. Skin Therapy Lett. 2002 Sep;7(7):1-2, 5. Pubmed
  • • 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
  • • Syed TA, Maibach HI: Butenafine hydrochloride: for the treatment of interdigital tinea pedis. Expert Opin Pharmacother. 2000 Mar;1(3):467-73. Pubmed
  • • 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
  • • Iwatani W, Arika T, Yamaguchi H: Two mechanisms of butenafine action in Candida albicans. Antimicrob Agents Chemother. 1993 Apr;37(4):785-8. Pubmed
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PATENTS

PATENTS

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