Naftifine

HCID 47641CAS 65472-88-0
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

Standard-SMILES
CN(C/C=C/c1ccccc1)Cc1cccc2ccccc12
InChIKey
OZGNYLLQHRPOBR-DHZHZOJOSA-N
Summenformel
C21H21N
Durchschnittliche Molmasse
287,4 g/mol
Monoisotopische Masse
287,16739967

Überblick

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.

Namen und Bezeichner

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

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,1
Polarare Oberfläche (TPSA)
3,2 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
5
Schwere Atome
22

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Pharmaceuticals -> Antibiotics

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

Sicherheit und Regulatorisches

Toxikologische Informationen

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

D - Dermatologicals

QD - Dermatologicals

Pharmacodynamics · 1 Eintrag

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 Eintrag

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 Einträge

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.

Verwendung und Herstellung

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

Zugehörige Reaktionen

0
Reaktionsaufzeichnung erstellen

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

Verknüpfte Notizen

Wird geladen…