TOLNAFTATE

US Approved OTC

First approved in 1965

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H17NOS
Molecular Weight	307.409
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C(=S)OC1=CC=C2C=CC=CC2=C1)C3=CC=CC(C)=C3

InChI

InChIKey=FUSNMLFNXJSCDI-UHFFFAOYSA-N

InChI=1S/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C19H17NOS
Molecular Weight	307.409
Charge	0
Count

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

Description
Sources: https://www.drugs.com/monograph/tolnaftate.html
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3524433

Tolnaftate is a thiocarbamate derivative used as an over-the-counter anti-fungal agent for treatment of athlete's foot and ringworm. Tolnaftate acts by inhibition of ergosterol biosynthesis pathway in fungal cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
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/3524433	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Tinea corporis 19 Sources: https://www.drugs.com/monograph/tolnaftate.html	Curative	Approved 8583	TINACTIN Approved Use Treatment of tinea corporis (body ringworm) and tinea cruris (jock itch) caused by Epidermophyton floccosum, Microsporum canis, M. audouinii, Trichophyton mentagrophytes, T. rubrum, or T. tonsurans.
Tinea cruris 11 Sources: https://www.drugs.com/monograph/tolnaftate.html	Curative	Approved 8583	TINACTIN Approved Use Treatment of tinea corporis (body ringworm) and tinea cruris (jock itch) caused by Epidermophyton floccosum, Microsporum canis, M. audouinii, Trichophyton mentagrophytes, T. rubrum, or T. tonsurans.
Tinea pedis 28 Sources: https://www.drugs.com/monograph/tolnaftate.html	Curative	Approved 8583	TINACTIN Approved Use Treatment of tinea pedis (athlete’s foot) and tinea manuum (hand ringworm) caused by E. floccosum, M. canis, M. audouinii, T. mentagrophytes, T. rubrum, or T. tonsurans.
Tinea manuum 3 Sources: https://www.drugs.com/monograph/tolnaftate.html	Curative	Approved 8583	TINACTIN Approved Use Treatment of tinea pedis (athlete’s foot) and tinea manuum (hand ringworm) caused by E. floccosum, M. canis, M. audouinii, T. mentagrophytes, T. rubrum, or T. tonsurans.
Pityriasis (Tinea) versicolor 1 Sources: https://www.drugs.com/monograph/tolnaftate.html	Curative	Approved 8583	TINACTIN Approved Use Treatment of pityriasis (tinea) versicolor caused by Malassezia furfur (Pityrosporum orbiculare or P. ovale).

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9620	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9620
ChemicalBook	CB4396231	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4396231
eMolecules	594916	https://www.emolecules.com/cgi-bin/more?vid=594916
MolPort	MolPort-002-893-958	https://www.molport.com/shop/molecule-link/MolPort-002-893-958
Selleck Chemicals	tolnaftate	http://www.selleckchem.com/products/tolnaftate.html
ZINC	ZINC000000057522	http://zinc15.docking.org/substances/ZINC000000057522

PubMed

Title	Date	PubMed
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013-09-05	23769903
Targeted protein depletion in Saccharomyces cerevisiae by activation of a bidirectional degron.	2010-12-29	21190544
Breast cancer biomarker discovery in the functional genomic age: a systematic review of 42 gene expression signatures.	2010-10-27	21082037
Sli15(INCENP) dephosphorylation prevents mitotic checkpoint reengagement due to loss of tension at anaphase onset.	2010-08-10	20619650
Identification of Hedgehog signaling inhibitors with relevant human exposure by small molecule screening.	2010-08	20434536
Assay of tolnaftate in human skin samples after in vitro penetration studies using high performance liquid chromatography.	2010-07-20	20635527
Development of high-yield autofluorescent protein microarrays using hybrid cell-free expression with combined Escherichia coli S30 and wheat germ extracts.	2010-06-15	20546627
One-hit wonders of genomic instability.	2010-05-19	20482869
Current concepts in systemic and topical therapy for superficial mycoses.	2010-03-04	20347665
Otomycosis: Diagnosis and treatment.	2010-03-04	20347664
Both interaction surfaces within cohesin's hinge domain are essential for its stable chromosomal association.	2010-02-23	20153193
Proteasome nuclear activity affects chromosome stability by controlling the turnover of Mms22, a protein important for DNA repair.	2010-02-19	20174551
In vitro antifungal activity of hydroxychavicol isolated from Piper betle L.	2010-02-03	20128889
Fungicide-driven evolution and molecular basis of multidrug resistance in field populations of the grey mould fungus Botrytis cinerea.	2009-12	20019793
Trichomycoses.	2009-07	20927231
Label-free detection of drug-membrane association using ultraviolet-visible sum-frequency generation.	2009-02-04	19140762
Conserved features of cohesin binding along fission yeast chromosomes.	2009	19454013
Efficient protein depletion by genetically controlled deprotection of a dormant N-degron.	2009	19401679
PTTG: an important target gene for ovarian cancer therapy.	2008-10-20	19014669
Heterologous expression of plasmodial proteins for structural studies and functional annotation.	2008-10-01	18828893
Are placebo-controlled trials of creams for athlete's foot still justified?	2008-09	18834482
Functional characterization of cohesin subunit SCC1 in Trypanosoma brucei and dissection of mutant phenotypes in two life cycle stages.	2008-08	18554326
E1 ubiquitin-activating enzyme UBA-1 plays multiple roles throughout C. elegans development.	2008-07-18	18636104
RIP and RALyase cleave the sarcin/ricin domain, a critical domain for ribosome function, during senescence of wheat coleoptiles.	2008-06-13	18395011
Cell-type-specific TEV protease cleavage reveals cohesin functions in Drosophila neurons.	2008-02	18267092
Inhibitory phosphorylation of separase is essential for genome stability and viability of murine embryonic germ cells.	2008-01	18232736
Displacement and re-accumulation of centromeric cohesin during transient pre-anaphase centromere splitting.	2007-12	17763979
Topical treatments for fungal infections of the skin and nails of the foot.	2007-07-18	17636672
Polo-like kinase controls vertebrate spindle elongation and cytokinesis.	2007-05-02	17476331
Identification of the C. elegans anaphase promoting complex subunit Cdc26 by phenotypic profiling and functional rescue in yeast.	2007-03-20	17374146
A multi-step pathway for the establishment of sister chromatid cohesion.	2007-01-19	17238288
PTTG is a secretory protein in human pituitary adenomas and in mouse pituitary tumor cell lines.	2007	17652795
ProFAT: a web-based tool for the functional annotation of protein sequences.	2006-10-23	17059594
The eggshell is required for meiotic fidelity, polar-body extrusion and polarization of the C. elegans embryo.	2006-10-16	17042944
[Use of topical antifungal agents].	2006-09-23	16989127
Study on the supramolecular multirecognition mechanism of beta-naphthol/beta-cyclodextrin/anionic surfactant in a tolnaftate hydrolysis system.	2006-05-04	16640448
Highly sensitive and selective spectrofluorimetric determination of tolnaftate through the formation of ternary inclusion complex of beta-naphthol/beta-cyclodextrin/anionic surfactant system.	2006-03-15	18970541
Nuclear distribution and chromatin association of DNA polymerase alpha-primase is affected by TEV protease cleavage of Cdc23 (Mcm10) in fission yeast.	2005-06-07	15941470
The identification of foam-forming soluble proteins from wheat (Triticum aestivum) dough.	2005-04	15789342
Shugoshin prevents dissociation of cohesin from centromeres during mitosis in vertebrate cells.	2005-03	15737064
Dissociation of cohesin from chromosome arms and loss of arm cohesion during early mitosis depends on phosphorylation of SA2.	2005-03	15737063
Biochemical characterization of terbinafine-resistant Trichophyton rubrum isolates.	2004-12	15682641
Validation of a liquid chromatography assay for the quantification of the Raf kinase inhibitor BAY 43-9006 in small volumes of mouse serum.	2004-09-25	15282098
Tolnaftate spray treatment during pregnancy.	2004-05	15082081
[Antimycotics suppress interleukin-4 and interleukin-5 production in anti-CD3 plus anti-CD28-stimulated T cells from patients with atopic dermatitis].	2004	15284827
Involvement of fatty acid pathways and cortical interaction of the pronuclear complex in Caenorhabditis elegans embryonic polarity.	2003-10-03	14527340
A study of dermatophytes and their in-vitro antifungal sensitivity.	2002-04	12696733
Ergosterol biosynthesis inhibition: a target for antifungal agents.	1995	8852337
[Synthesis and antifungal activity of butenafine hydrochloride (KP-363), a new benzylamine antifungal agent].	1991-02	2056447
Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate.	1986-05	3524433

Patents

Sample Use Guides

In Vivo Use Guide

Apply topically to the infected skin as a 1% cream, aerosol liquid spray, aerosol powder spray, powder, or solution.

Route of Administration: Topical

In Vitro Use Guide

Ergosterol biosynthesis in fungal cells from Candida albicans, Candida parapsilosis and Trichophyton mentagrophytes was measured by incubation of cells were incubated with [U-14C]acetate at pH 6.5 for 2 hrs and quantification of nonsaponifiable lipids by thin layer chromatography. Tolnaftate inhibited ergosterol biosynthesis with IC50 of about 0.1-1.0 mg/l.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:36:50 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:50 GMT 2025`
Record UNII	06KB629TKV
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TOLNAFTATE

Official Name

English

SEPARIN

Preferred Name

English

NSC-233648

Code

English

TOLNAFTATE [VANDF]

Common Name

English

TOLNAFTATE [EP MONOGRAPH]

Common Name

English

O-2-NAPHTHYL M,N-DIMETHYLTHIOCARBANILATE

Common Name

English

SCH 10144

Code

English

TOLNAFTATE [USP-RS]

Common Name

English

CARBAMOTHIOIC ACID, METHYL(3-METHYLPHENYL)-, O-2-NAPHTHALENYL ESTER

Common Name

English

SCH-10144

Code

English

Tolnaftate [WHO-DD]

Common Name

English

tolnaftate [INN]

Common Name

English

TOLNAFTATE [JAN]

Common Name

English

TOLNAFTATE [MI]

Common Name

English

TOLNAFTATE [USP MONOGRAPH]

Common Name

English

TOLNAFTATE [GREEN BOOK]

Common Name

English

TOLNAFTATE [USAN]

Common Name

English

TOLNAFTATE [MART.]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QD01AE18