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About This Item
Empirical Formula (Hill Notation):
C21H21N · HCl
CAS Number:
Molecular Weight:
323.86
NACRES:
NA.76
PubChem Substance ID:
UNSPSC Code:
51102829
MDL number:
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
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Related Categories
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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Lawrence Charles Parish et al.
Journal of drugs in dermatology : JDD, 10(11), 1282-1288 (2011-11-05)
Naftifine HCl 2% cream (NAFT-2) is a topical allylamine antifungal agent under development in the United States. This randomized, double-blind, vehicle-controlled, phase 3 trial evaluated the efficacy and safety of two weeks of NAFT-2 treatment in subjects with tinea pedis.
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
Aditya K Gupta et al.
Journal of cutaneous medicine and surgery, 12(2), 51-58 (2008-03-19)
Naftifine is a topical allylamine that is effective and safe in the management of superficial dermatomycoses. Naftifine is fungicidal in vitro against a broad spectrum of dermatophyte fungi and provides good activity against Candida and Aspergillus species. It is also
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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