Naftifine

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 Search

SMILES

CN(C\C=C\C1=CC=CC=C1)CC2=C3C=CC=CC3=CC=C2

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00735
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/naftin.html

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 Target	Pharmacology	Potency
Squalene monooxygenase 10 Target ID: CHEMBL3592 Sources: http://www.drugbank.ca/drugs/DB00735	Inhibitor 8504
Squalene monooxygenase 10 Target ID: CHEMBL2364679 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8834895	Inhibitor 8504	114.6 nM [IC50]
Squalene monooxygenase 10 Target ID: Q92206 Gene ID: 3646458\|\|\|3646509 Gene Symbol: ERG1 Target Organism: Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3877503	Inhibitor 8504	1.1 µM [Ki]
Lymphoma cell line 2 Target ID: CHEMBL614114 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26504016	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tinea pedis 28 Sources: https://www.drugs.com/pro/naftin.html	Curative		Approved 8583	Naftin Approved Use Naftin Cream is an allylamine antifungal indicated for the treatment of interdigital tinea pedis, tinea cruris, and tinea corporis caused by the organism Trichophyton rubrum. Launch Date 2012
Tinea corporis 19 Sources: https://www.drugs.com/pro/naftin.html	Curative		Approved 8583	Naftin Approved Use Naftin Cream is an allylamine antifungal indicated for the treatment of interdigital tinea pedis, tinea cruris, and tinea corporis caused by the organism Trichophyton rubrum. Launch Date 2012

C_max

Value	Dose	Analyte	Population
7 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	6.4 g single, topical dose: 6.4 g route of administration: Topical experiment type: SINGLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	6.4 g 1 times / day multiple, topical dose: 6.4 g route of administration: Topical experiment type: MULTIPLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.21 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	8.1 g single, topical dose: 8.1 g route of administration: Topical experiment type: SINGLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
12.7 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	8.1 g 1 times / day multiple, topical dose: 8.1 g route of administration: Topical experiment type: MULTIPLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
3.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	2.3 g single, topical dose: 2.3 g route of administration: Topical experiment type: SINGLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
3.31 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	2.3 g 1 times / day multiple, topical dose: 2.3 g route of administration: Topical experiment type: MULTIPLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
117 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	6.4 g single, topical dose: 6.4 g route of administration: Topical experiment type: SINGLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
204 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	6.4 g 1 times / day multiple, topical dose: 6.4 g route of administration: Topical experiment type: MULTIPLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
138 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	8.1 g single, topical dose: 8.1 g route of administration: Topical experiment type: SINGLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
192 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	8.1 g 1 times / day multiple, topical dose: 8.1 g route of administration: Topical experiment type: MULTIPLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN
49.8 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	2.3 g single, topical dose: 2.3 g route of administration: Topical experiment type: SINGLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
52.4 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	2.3 g 1 times / day multiple, topical dose: 2.3 g route of administration: Topical experiment type: MULTIPLE co-administered:	NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.5 day DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/019356s008,019599s014,204286s003lbl.pdf	6.4 g single, topical dose: 6.4 g route of administration: Topical experiment type: SINGLE co-administered:		NAFTIFINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 % 1 times / day multiple, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019599s013lbl.pdf	unhealthy, 9 (2-18) Health Status: unhealthy Age Group: 9 (2-18) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019599s013lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019599s013lbl.pdf
2 % 1 times / day multiple, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019599s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019599s013lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/019599s013lbl.pdf
2 % 1 times / day multiple, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204286Orig1s000MedR.pdf	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204286Orig1s000MedR.pdf	Disc. AE: Application site fissure, Hypersensitivity... AEs leading to discontinuation/dose reduction: Application site fissure (grade 3-4) Hypersensitivity (grade 2-3) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204286Orig1s000MedR.pdf

AEs

AE	Significance	Dose	Population
Hypersensitivity	grade 2-3 Disc. AE	2 % 1 times / day multiple, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204286Orig1s000MedR.pdf	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204286Orig1s000MedR.pdf
Application site fissure	grade 3-4 Disc. AE	2 % 1 times / day multiple, topical Recommended Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204286Orig1s000MedR.pdf	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/204286Orig1s000MedR.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 303 UGT 219

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/3964331/	yes
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/3964331/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7451	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7451
ZINC	ZINC000001530977	http://zinc15.docking.org/substances/ZINC000001530977

PubMed

Title	Date	PubMed
Azole antifungal agents related to naftifine and butenafine.	2000-06	10909187
Effects of naftifine and terbinafine, two allylamine antifungal drugs, on selected functions of human polymorphonuclear leukocytes.	1994-11	7872755
[Synthesis and antifungal activity of butenafine hydrochloride (KP-363), a new benzylamine antifungal agent].	1991-02	2056447
Effect of the antimycotic drug naftifine on growth of and sterol biosynthesis in Candida albicans.	1984-04	6375557
In vitro activity of naftifine, a new antifungal agent.	1981-03	7247366

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 Created by `admin` on `Mon Mar 31 18:06:43 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:43 GMT 2025`
Record UNII	4FB1TON47A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Naftifine

Official Name

English

NAFT-500

Preferred Name

English

Naftifine [WHO-DD]

Common Name

English

NAFTIFINE [MI]

Common Name

English

NAFTIFINE [VANDF]

Common Name

English

AW-105-843

Code

English

naftifine [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QD01AE22