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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

Key Documents

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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)
Athlete's foot.
Fay Crawford
Clinical evidence, (11)(11), 2128-2132 (2005-01-18)
J J Goday et al.
Journal of the European Academy of Dermatology and Venereology : JEADV, 11(1), 72-73 (1998-09-10)
Allergic contact dermatitis from naftifine has been scarcely described in the English literature, all of them in adults. We report a case of a 12-year-old girl who developed an acute eczema on her neck after application of a naftifine cream.
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
Naftifine, a topical allylamine.
Shellie Marks et al.
Journal of drugs in dermatology : JDD, 9(7), 750-750 (2010-08-04)
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