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Naftifine

Naftifine 구조식 이미지
카스 번호:
65472-88-0
상품명:
Naftifine
동의어(영문):
Naftin;naftifin;Exoderil;NAFTIFINE;AW-105-843;SN-105-843;Naftifungin;Naftifinebase;Naftifine USP/EP/BP;n-trans-cinnamyl-n-methyl-(1-naphthylmethyl)amine
CBNumber:
CB5211922
분자식:
C21H21N
포뮬러 무게:
287.4
MOL 파일:
65472-88-0.mol

Naftifine 속성

녹는점
177 °C
끓는 점
bp0.015 torr 162-167°
밀도
1.082±0.06 g/cm3(Predicted)
산도 계수 (pKa)
7.99±0.50(Predicted)
Merck
6355
CAS 데이터베이스
65472-88-0(CAS DataBase Reference)

안전

HS 번호 29214990

Naftifine C화학적 특성, 용도, 생산

Originator

Naftifine,Sandoz (Novartis)

용도

Naftifine (Naftin) is a synthetic allylamine derivative topical antifungal agent that works by blocking squalene 2,3-epoxidase, resulting in increased cell membrane permeability and cell death. It is structurally and pharmacologically related to terbinafine. It also has some antiinflammatory properties that may be due to its ability to alter chemotaxis by polymorphonucleocytes. It is most effective against dermatophytes, moderately active against molds, and less active against yeasts, including C. albicans.

용도

Naftifine is only permitted to be used externally and only superficially as a drug with a broad spectrum of action against dermatophytes and candida infections. According to the initial data, it exceeds the activity of econazole. Moreover, it does not have a locally irritating effect. It is believed that the fungicide activity of this drug is based on its ability to inhibit the fungal enzyme squalene epoxidase, thus lowering the concentration of ergosterol. The corresponding enzyme in mammals is inhibited significantly less. Synonyms of this drug are exoderil, naftin, and others.

용도

(E)-Naftifine is an intermediate in synthesizing Naftifine N-Oxide (N213110), which is an impurity or metabolite of Naftifine Hydrochloride (N213100), an allylamine antifungal agent.

정의

ChEBI: A tertiary amine in which the nitrogen is substituted by methyl, alpha-naphthylmethyl, and (1E)-cinnamyl groups. It is used (usually as its hydrochloride salt) for the treatment of fungal skin infections.

Indications

Naftifine (Naftin) is a synthetic allylamine derivative topical antifungal agent that works by blocking squalene 2,3-epoxidase, resulting in increased cell membrane permeability and cell death. It is structurally and pharmacologically related to terbinafine. It also has some antiinflammatory properties that may be due to its ability to alter chemotaxis by polymorphonucleocytes. It is most effective against dermatophytes, moderately active against molds, and less active against yeasts, including C. albicans.

Manufacturing Process

To a mixture of 1.42 g of methyl-(1-naphthylmethyl)amine hydrochloride, 2.89 g of sodium carbonate and 10 ml of dimethylformamide is added, at room temperature, 1.25 g of cinnamyl chloride, dropwise. After 18 hours stirring, at room temperature, the mixture is filtered and the filtrate is evaporated in vacuo. The residue is dissolved in toluene and, after drying over sodium sulphate, evaporated to obtain the trans-N-(cinnamylmethyl)-Nmethyl-(1-naphthylmethyl)amine compound, boiling point 162-167°C/0.015 Torr.
The free base may be converted, with isopropanolic hydrogen chloride solution, into the hydrochloride form, melting point 177°C (from propanol).

상표명

Naftin (Merz).

Therapeutic Function

Antifungal

Synthesis Reference(s)

Journal of Medicinal Chemistry, 29, p. 112, 1986 DOI: 10.1021/jm00151a019
Tetrahedron Letters, 25, p. 2535, 1984 DOI: 10.1016/S0040-4039(01)81224-7

Pharmaceutical Applications

A topical antifungal used as a 1% cream for the treatment of dermatophytoses, including tinea pedis, tinea corporis and tinea cruris.

Clinical Use

Naftifine was the first allyl amine to be discovered and marketed. It is subject to extensive first-pass metabolism to be orally active and, consequently, is only available in topical preparations. The widest use of naftifine is against various tinea infections of the skin.

Chemical Synthesis

Naftifine, (E)-N-methyl-N-(3-phenyl-2-propenyl)-1-naphthalinmethanamine (35.3.1), is synthesized by alkylating N-methyl-(1-naphthylmethyl)-amine with cinnamyl chloride in the presence of sodium carbonate.

Naftifine 준비 용품 및 원자재

원자재

준비 용품


Naftifine 공급 업체

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