[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine

• ChemBase ID: 962
• Molecular Formular: C23H27N
• Molecular Mass: 317.46718
• Monoisotopic Mass: 317.21434987
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 101828-21-1
• PubChem SID: 160964425; 46506191
• PubChem CID: 2484

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.8725023
• LogD (pH = 7.4): 4.343121
• Log P: 6.173649
• Molar Refractivity: 104.3294 cm^3
• Polarizability: 42.022823 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.85
• LOG S: -6.62
• Solubility (Water): 7.56e-05 g/l

PROPERTIES

Physical Property

• Solubility: Slightly soluble (HCl salt)
• Hydrophobicity(logP): 6.6

DETAILS

DrugBank - DB01091

• 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

• 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