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N1790

Sigma-Aldrich

Naftifine hydrochloride

Synonym(s):

Naftifine HCL

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About This Item

Empirical Formula (Hill Notation):
C21H21N · HCl
CAS Number:
65473-14-5
Molecular Weight:
323.86
MDL number:
MFCD00059047
UNSPSC Code:
51102829
PubChem Substance ID:
329818590
NACRES:
NA.76

Assay

≥99%

Quality Level

200

form

powder

solubility

ethanol: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
fungi
yeast

Mode of action

cell wall synthesis | interferes
enzyme | inhibits

storage temp.

2-8°C

SMILES string

Cl.CN(C\C=C\c1ccccc1)Cc2cccc3ccccc23

InChI

1S/C21H21N.ClH/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20;/h2-15H,16-17H2,1H3;1H/b11-8+;

InChI key

OLUNPKFOFGZHRT-YGCVIUNWSA-N

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Application

Naftifine is a synthetic, broad spectrum, antifungal agent and allylamine derivative. It is used topically to treat superficial dermatomycoses such as tinea pedis, tinea cruris, and tinea corporis.

Biochem/physiol Actions

Naftifine is an allylamine compound that has antifungal and antimycotic activities. Naftifine inhibits fungal squalene epoxidase and prevents ergosterol biosynthesis. Naftifine also has antibiotic activity against Gram-positive and Gram-negative bacteria. It has demonstrated anti-inflammatory properties such as a reduction in superoxide production and a reduction in polymorphonuclear leukocyte chemotaxis/endothelial adhesion. Naftifine appears to interfere with sterol biosynthesis by inhibiting the squalene 2,3-epoxidase. This inhibition results in decreased amounts of ergosterol and an accumulation of squalene in the cells.
Allylamine compound that has antifungal and antimycotic activities. Naftifine inhibits fungal squalene epoxidase and prevents ergosterol biosynthesis. Naftifine also has antibiotic activity against Gram-positive and Gram-negative bacteria and has demonstrated anti-inflammatory properties.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Light sensitive.

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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Allergic contact dermatitis to naftifine.
Monica Corazza et al.
Contact dermatitis, 53(5), 302-303 (2005-11-15)
Muhterem Polat et al.
Mycoses, 50(6), 525-526 (2007-10-20)
The patient we present herein is a 6-month-old infant who had erythema and scaling on the central part of the face for 4 months. Both the abundant scaling and the localisation, but also the low age of this infant led
Athlete's foot.
Fay Crawford
Clinical evidence, (11)(11), 2128-2132 (2005-01-18)
Michael H Gold et al.
Journal of drugs in dermatology : JDD, 11(4), 514-518 (2012-03-29)
Topical antifungal treatment is a mainstay of therapy for Seborrehic Dermatitis (SD). Although the amidazole and ciclopyridine antifungals have been extensively studied, few clinical efficacy data are available for topical allylamine therapy in SD. The objective of this open-label exploratory
Maite Uzqueda et al.
Pharmaceutical research, 23(5), 980-988 (2006-05-23)
Naftifine (NF) is an antifungal drug poorly soluble in basic aqueous solutions. Complexation with cyclodextrins (CDs) improves the physicochemical characteristics of many drugs. The aim of this work is to characterize the interactions between NF and alpha-CD, beta-CD, hydroxypropylbeta-CD, methylbeta-CD
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