U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C21H21N
Molecular Weight 287.3981
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NAFTIFINE

SMILES

CN(C\C=C\C1=CC=CC=C1)CC2=CC=CC3=CC=CC=C23

InChI

InChIKey=OZGNYLLQHRPOBR-DHZHZOJOSA-N
InChI=1S/C21H21N/c1-22(16-8-11-18-9-3-2-4-10-18)17-20-14-7-13-19-12-5-6-15-21(19)20/h2-15H,16-17H2,1H3/b11-8+

HIDE SMILES / InChI

Molecular Formula C21H21N
Molecular Weight 287.3981
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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. 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. Naftifine is used for the topical treatment of tinea pedis, tinea cruris, and tinea corporis caused by the organisms Trichophyton rubrum, Trichophyton mentagrophytes, Trichophyton tonsurans and Epidermophyton floccosum. Marketed as Naftin.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
114.6 nM [IC50]
1.1 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Naftin
Curative
Naftin

Cmax

ValueDoseCo-administeredAnalytePopulation
9.21 ng/mL
8.1 g single, topical
NAFTIFINE plasma
Homo sapiens
12.7 ng/mL
8.1 g 1 times / day multiple, topical
NAFTIFINE plasma
Homo sapiens
7 ng/mL
6.4 g single, topical
NAFTIFINE plasma
Homo sapiens
11 ng/mL
6.4 g 1 times / day multiple, topical
NAFTIFINE plasma
Homo sapiens
3.6 ng/mL
2.3 g single, topical
NAFTIFINE plasma
Homo sapiens
3.31 ng/mL
2.3 g 1 times / day multiple, topical
NAFTIFINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
138 ng × h/mL
8.1 g single, topical
NAFTIFINE plasma
Homo sapiens
192 ng × h/mL
8.1 g 1 times / day multiple, topical
NAFTIFINE plasma
Homo sapiens
117 ng × h/mL
6.4 g single, topical
NAFTIFINE plasma
Homo sapiens
204 ng × h/mL
6.4 g 1 times / day multiple, topical
NAFTIFINE plasma
Homo sapiens
49.8 ng × h/mL
2.3 g single, topical
NAFTIFINE plasma
Homo sapiens
52.4 ng × h/mL
2.3 g 1 times / day multiple, topical
NAFTIFINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.5 day
6.4 g single, topical
NAFTIFINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
For topical use only. NAFTIN Cream is not for ophthalmic, oral or intravaginal use. Apply a thin layer of NAFTIN Cream once-daily to the affected areas plus a ½ inch margin of healthy surrounding skin for 2 weeks.
Route of Administration: Topical
In Vitro Use Guide
The anti-tumor apoptotic effect of naftifine at doses ranging from 0.1-200 uM was investigated on two human and one murine lymphoma. Naftifine significantly reduced cell viability in all tested myeloma and lymphoma cell lines in a dose-dependent manner.
Substance Class Chemical
Record UNII
4FB1TON47A
Record Status Validated (UNII)
Record Version