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B5188

Sigma-Aldrich

Butenafine hydrochloride

≥98% (HPLC)

Synonym(s):

Butenafine hydrochloride, Mentax, N-(p-tert-butylbenzyl)-N-methyl-1-naphthalenemethylamine hydrochloride, N-[[4-(1,1-Dimethylethyl)phenyl]methyl]-N-methyl-1-naphthalenemethanamine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C23H27N · HCl
CAS Number:
101827-46-7
Molecular Weight:
353.93
MDL number:
MFCD00917064
UNSPSC Code:
51111800
PubChem Substance ID:
329773252
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: ≥10 mg/mL

originator

Schering Plough

storage temp.

room temp

SMILES string

Cl.CN(Cc1ccc(cc1)C(C)(C)C)Cc2cccc3ccccc23

InChI

1S/C23H27N.ClH/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;1H

InChI key

LJBSAUIFGPSHCN-UHFFFAOYSA-N

General description

Butenafine hydrochloride is chemically known as N-4-tertbutylbenzyl-N-methyl-1-naphthalenemethylamine hydrochloride. Butenafine, a benzylamine derivative, is a new generation antimycotic compound. It is easily soluble in methanol, ethanol, dichloromethane, and chloroform, but not in water. The allyl radical in butenafine hydrochloride is substituted by a butylbenzyl group.

Application

Butenafine hydrochloride has been used as a standard in high-performance liquid chromatography (HPLC) method to determine butenafine hydrochloride in butenafine-loaded nanosponges.

Biochem/physiol Actions

Butenafine exhibits fungicidal and antimycotic activity. This fungal squalene epoxidase inhibitor serves as an effective fungicide against T. rubrum, T. mentagrophytes, Microsporum canis, Aspergillus fumigatus, Sporothrix schenckii, Candida parapsilosis, and C. albicans. It is considered more effective and rapid than other antifungal drugs at curing dermatophytosis and preventing recurrences. In humans, it is used topically to treat tinea conditions and superficial candidiasis. Butenafine is considered a promising antimycotic compound to treat tinea pedis due to its efficiency, safety profile, relapse rates, and cost-effectiveness.
Butenafine possesses antifungal property. It is a squalene epoxidase inhibitor. Butenafine can inhibit the synthesis of ergosterol needed in fungal cell membranes.

Features and Benefits

This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H312

Hazard Classifications

Acute Tox. 4 Dermal

Storage Class Code

11 - Combustible Solids

WGK

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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1453888
Ansari MJ, et al.
Journal of Pharmaceutical Research International, 116-125 (2020)
Adriana Bezerra-Souza et al.
Pharmaceutics, 11(7) (2019-07-25)
Leishmaniasis is a neglected tropical disease affecting more than 12 million people worldwide, which in its visceral clinical form (VL) is characterised by the accumulation of parasites in the liver and spleen, and can lead to death if not treated.
T A Syed et al.
Expert opinion on pharmacotherapy, 1(3), 467-473 (2001-03-16)
Butenafine, a derivative of benzylamine with potent fungicidal activity is a new generation of antimycotic compound that has shown to be extremely effective against experimentally-induced tinea pedis in the guinea-pig, a situation that resembles synergetic pathology similar to that of

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