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Merck

N1790

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
NACRES:
NA.76
PubChem Substance ID:
329818590
UNSPSC Code:
51102829
MDL number:
MFCD00059047

assay

≥99%

form

powder

InChI key

OLUNPKFOFGZHRT-YGCVIUNWSA-N

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+;

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

Quality Level

200

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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

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.
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.

Other Notes

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

Storage Class

11 - Combustible Solids

wgk

nwg

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000350741
0000350741
SLCQ3069
SLCK3331
MKBR6134V

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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
Ruifeng Zhang et al.
Medical mycology, 49(1), 90-93 (2010-07-29)
We report a rare case of kerion celsi of the scalp caused by Microsporum gypseum in a boy 1 month after he received dermatoplasty for a scalp injury from a road accident. Species identification was performed by observation of morphologic
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