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Naftifine hydrochloride

Names

[ CAS No. ]:
65473-14-5

[ Name ]:
Naftifine hydrochloride

[Synonym ]:
(2E)-N-méthyl-N-(naphtalén-1-ylméthyl)-3-phénylprop-2-én-1-amine chlorhydrate
(2E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine hydrochloride (1:1)
MFCD00059047
(2E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine hydrochloride
(2E)-N-Methyl-N-(1-naphthylmethyl)-3-phenyl-2-propen-1-amine hydrochloride (1:1)
1-naphthalenemethanamine, N-methyl-N-[(2E)-3-phenyl-2-propenyl]-, hydrochloride
(E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine,hydrochloride
(2E)-N-Methyl-N-(1-naphthylmethyl)-3-phenylprop-2-en-1-amine hydrochloride (1:1)
(2E)-N-Methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-aminhydrochlorid
1-Naphthalenemethanamine, N-methyl-N-[(2E)-3-phenyl-2-propen-1-yl]-, hydrochloride (1:1)
Naftifine HCl

Biological Activity

[Description]:

Naftifine Hydrochloride is a synthetic, broad spectrum, antifungal agent.Target: AntifungalNaftifine exhibits an interesting in vitro spectrum of activity against dermatophytes (38 strains; minimal inhibitory concentration (MIC) range 0.1 to 0.2 mg/mL), aspergilli (6 strains; MIC range, 0.8 to 12.5 mg/mL), Sporothrix schenckii (2 strains; MICs, 0.8 and 1.5 mg/mL), and yeasts of the genus Candida (77 strains; MIC range, 1.5 to greater than 100 mg/mL) [1]. The MIC of naftifine for C. albicans Δ63 is 100 mg/L in Sabouraud medium (initial pH 6.5). Naftifine (50 mg/L) gives greater than 99% inhibition of sterol biosynthesis both in whole cells and in cell extracts of C. albicans. The primary action of naftifine appears to be the blocking of fungal squalene epoxidation [2].Naftifine HCl 2% cream results in clinical cure rate and clinical success rate of 33% and 84% after treatment for 4 weeks, and week 2 efficacy response rates in Naftifine HCl 2% subjects are all lower than at week 4 but are significantly higher than week 2 vehicle-treated counterparts [3]. Naftifine causes interruption of fungal ergosterol synthesis and accumulation of squalene in fungal organisms. Naftifine also has demonstrated anti-inflammatory properties such as a reduction in superoxide production and a reduction in polymorphonuclear leukocyte chemotaxis/endothelial adhesion. Naftifine has shown good efficacy and safety for a variety of conditions and is a useful treatment that provides both antifungal action and relief of inflammatory signs and symptoms. Few adverse events have been noted with naftifine use, the most frequent being mild and transient burning, stinging, or itching in the application area [4].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal
Research Areas >> Infection

[References]

[1]. Georgopoulos, A., et al., In vitro activity of naftifine, a new antifungal agent. Antimicrob Agents Chemother, 1981. 19(3): p. 386-9.

[2]. Ryder, N.S., G. Seidl, and P.F. Troke, Effect of the antimycotic drug naftifine on growth of and sterol biosynthesis in Candida albicans. Antimicrob Agents Chemother, 1984. 25(4): p. 483-7.

[3]. Parish, L.C., et al., A double-blind, randomized, vehicle-controlled study evaluating the efficacy and safety of naftifine 2% cream in tinea cruris. J Drugs Dermatol, 2011. 10(10): p. 1142-7.

[4]. Gupta, A.K., J.E. Ryder, and E.A. Cooper, Naftifine: a review. J Cutan Med Surg, 2008. 12(2): p. 51-8.


[Related Small Molecules]

Cycloheximide | Hygromycin B | Cancidas | 5-Flucytosine | Posaconazole | Terbinafine | Ciclopirox | Isavuconazole | Anidulafungin | Clotrimazole | Clioquinol | Miconazole Nitrate | Pimaricin | Ascomycin | Econazole (nitrate)

Chemical & Physical Properties

[ Boiling Point ]:
440.1ºC at 760 mmHg

[ Melting Point ]:
172-175ºC

[ Molecular Formula ]:
C21H22ClN

[ Molecular Weight ]:
323.859

[ Flash Point ]:
194.4ºC

[ Exact Mass ]:
323.144073

[ PSA ]:
3.24000

[ LogP ]:
5.78700

[ Storage condition ]:
-20?C Freezer

MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2942000000

Customs

[ HS Code ]: 2942000000

Articles

DrugBank 3.0: a comprehensive resource for 'omics' research on drugs.

Nucleic Acids Res. 39 , D1035-41., (2011)

DrugBank (http://www.drugbank.ca) is a richly annotated database of drug and drug target information. It contains extensive data on the nomenclature, ontology, chemistry, structure, function, action, ...

Allergic contact dermatitis from naftifine in a child without cross-reaction to terbinafine.

J. Eur. Acad. Dermatol. Venereol. 11(1) , 72-3, (1998)

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 nec...

RIPK3-mediated necroptosis regulates cardiac allograft rejection.

Journal. of. Drugs in. Dermatology. 10(11) , 1282-8, (2011)

Cell death results in tissue damage and ultimately donor graft rejection and can occur as an active molecular process through apoptotic, necrotic and newly identified receptor interacting protein 1 an...


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Related Compounds