Naftifine

HCID 47641CAS 65472-88-0
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Basic information

Standard SMILES
CN(C/C=C/c1ccccc1)Cc1cccc2ccccc12
InChIKey
OZGNYLLQHRPOBR-DHZHZOJOSA-N
Molecular formula
C21H21N
Average molar mass
287.4 g/mol
Monoisotopic mass
287.16739967

Overview

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.

Names & identifiers

Preferred name
Naftifine
IUPAC
(E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine

Names & synonyms

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

Database identifiers

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

Properties

Computed structural properties

XLogP
5.1
Topological polar surface area
3.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
5
Heavy atoms
22

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Pharmaceuticals -> Antibiotics

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

Safety & regulation

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemistry & industry

Pharmacology

ATC Code · 2 items

D - Dermatologicals

QD - Dermatologicals

Pharmacodynamics · 1 item

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 <i>Trichophyton rubrum</i>, <i>Trichophyton mentagrophytes</i>, <i>Trichophyton tonsurans</i>, <i>Epidermophyton floccosum</i>, and <i>Microsporum canis</i>, <i>Microsporum audouini</i>, and <i>Microsporum gypseum</i>; and fungistatic activity against <i>Candida</i> species including <i>Candida albicans</i>. However it is only used to treat the organisms listed in the indications.

Mechanism of Action · 1 item

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 items

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.

Uses & manufacturing

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

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