Naftifine

HCID 47641CAS 65472-88-0

基本情報

標準SMILES: CN(C/C=C/c1ccccc1)Cc1cccc2ccccc12
InChIKey: OZGNYLLQHRPOBR-DHZHZOJOSA-N
分子式: C21H21N
平均分子量: 287.4 g/mol
単同位体質量: 287.16739967

概要

Naftifine is 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. It has a role as an EC 1.14.13.132 (squalene monooxygenase) inhibitor and a sterol biosynthesis inhibitor. It is a member of naphthalenes, a tertiary amine and an allylamine antifungal drug.

名称と識別子

優先名称: Naftifine
IUPAC: (E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine

名称と別名

Naftifine65472-88-0NaftifinaNaftifinumNaftifinNaft-5004FB1TON47ACHEBI:7451AW-105-843DTXSID6048545RefChem:57001methyl(naphthalen-1-ylmethyl)(3-phenylprop-2-en-1-yl)amine

名称をさらに表示

DTXCID6028101D01AE22(E)-Naftifine(E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine(E)-N-Cinnamyl-N-methyl-1-naphthalenemethylamineNaftifine (INN)CHEMBL626methyl[(naphthalen-1-yl)methyl](3-phenylprop-2-en-1-yl)amine

データベース識別子

CAS: 65472-88-0
PubChem CID: 47641
DTXSID: DTXSID6048545
ChEMBL: CHEMBL626
ChEBI: CHEBI:7451
UNII: 4FB1TON47A
Nikkaji: J19.990G、J3.124.773J

物性

構造計算による物性

XLogP: 5.1
極性表面積: 3.2 Å²
水素結合供与体数: 0
水素結合受容体数: 1
回転可能結合数: 5
重原子数: 22
形式電荷: 0
複雑度: 342

実験および物理化学的性質

Drugs · 3 件

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Pharmaceuticals -> Antibiotics

Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antifungal Agents

安全と法規制

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

化学と産業

薬理情報

ATC Code · 2 件

D - Dermatologicals

QD - Dermatologicals

Pharmacodynamics · 1 件

Naftifine is a synthetic, broad spectrum, antifungal agent and allylamine derivative. The following in vitro data are available, but their clinical significance is unknown. Naftifine has been shown to exhibit fungicidal activity in vitro against a broad spectrum of organisms including Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans, Epidermophyton floccosum, and Microsporum canis, Microsporum audouini, and Microsporum gypseum; and fungistatic activity against Candida species including Candida albicans. However it is only used to treat the organisms listed in the indications.

Mechanism of Action · 1 件

Although the exact mechanism of action against fungi is not known, naftifine appears to interfere with sterol biosynthesis by inhibiting the enzyme squalene 2,3-epoxidase. This inhibition of enzyme activity results in decreased amounts of sterols, especially ergosterol, and a corresponding accumulation of squalene in the cells.

Biological Half-LifeApproximately 2 to 3 days following topical administration.

FDA Pharmacological Classification · 5 件

4FB1TON47A

NAFTIFINE

Chemical Structure [CS] - Allylamine

Established Pharmacologic Class [EPC] - Allylamine Antifungal

Naftifine is an Allylamine Antifungal.

MeSH Pharmacological ClassificationSubstances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.

用途と製造

UsesUse (kg; approx.) in Germany (2009): >10