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(C)=CC=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

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 8146

Conditions

Condition	Modality	Highest Phase	Product
Tinea corporis 19 Sources: https://www.drugs.com/monograph/tolnaftate.html	Curative	Approved 8307	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 8307	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 8307	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 8307	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 8307	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
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
eMolecules	594916	https://www.emolecules.com/cgi-bin/more?vid=594916

PubMed

Title	Date	PubMed
Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate.	1986 May	3524433
[Synthesis and antifungal activity of butenafine hydrochloride (KP-363), a new benzylamine antifungal agent].	1991 Feb	2056447
Ergosterol biosynthesis inhibition: a target for antifungal agents.	1995	8852337
Securin is not required for cellular viability, but is required for normal growth of mouse embryonic fibroblasts.	2001 Aug 7	11516952
Anti-mycotics suppress interleukin-4 and interleukin-5 production in anti-CD3 plus anti-CD28-stimulated T cells from patients with atopic dermatitis.	2001 Dec	11886533
Evolutionary lines of cysteine peptidases.	2001 May	11517925
A study of dermatophytes and their in-vitro antifungal sensitivity.	2002 Apr	12696733
The anaphase-promoting complex and separin are required for embryonic anterior-posterior axis formation.	2002 Feb	11832245
[Antimycotics suppress interleukin-4 and interleukin-5 production in anti-CD3 plus anti-CD28-stimulated T cells from patients with atopic dermatitis].	2004	15284827
Biochemical characterization of terbinafine-resistant Trichophyton rubrum isolates.	2004 Dec	15682641
The identification of foam-forming soluble proteins from wheat (Triticum aestivum) dough.	2005 Apr	15789342
Nuclear distribution and chromatin association of DNA polymerase alpha-primase is affected by TEV protease cleavage of Cdc23 (Mcm10) in fission yeast.	2005 Jun 7	15941470
Highly sensitive and selective spectrofluorimetric determination of tolnaftate through the formation of ternary inclusion complex of beta-naphthol/beta-cyclodextrin/anionic surfactant system.	2006 Mar 15	18970541
Study on the supramolecular multirecognition mechanism of beta-naphthol/beta-cyclodextrin/anionic surfactant in a tolnaftate hydrolysis system.	2006 May 4	16640448
[Use of topical antifungal agents].	2006 May-Jun	16989127
ProFAT: a web-based tool for the functional annotation of protein sequences.	2006 Oct 23	17059594
Displacement and re-accumulation of centromeric cohesin during transient pre-anaphase centromere splitting.	2007 Dec	17763979
A multi-step pathway for the establishment of sister chromatid cohesion.	2007 Jan 19	17238288
Topical treatments for fungal infections of the skin and nails of the foot.	2007 Jul 18	17636672
Identification of the C. elegans anaphase promoting complex subunit Cdc26 by phenotypic profiling and functional rescue in yeast.	2007 Mar 20	17374146
Polo-like kinase controls vertebrate spindle elongation and cytokinesis.	2007 May 2	17476331
PTTG is a secretory protein in human pituitary adenomas and in mouse pituitary tumor cell lines.	2007 Spring	17652795
Functional characterization of cohesin subunit SCC1 in Trypanosoma brucei and dissection of mutant phenotypes in two life cycle stages.	2008 Aug	18554326
Cell-type-specific TEV protease cleavage reveals cohesin functions in Drosophila neurons.	2008 Feb	18267092
Inhibitory phosphorylation of separase is essential for genome stability and viability of murine embryonic germ cells.	2008 Jan	18232736
E1 ubiquitin-activating enzyme UBA-1 plays multiple roles throughout C. elegans development.	2008 Jul 18	18636104
RIP and RALyase cleave the sarcin/ricin domain, a critical domain for ribosome function, during senescence of wheat coleoptiles.	2008 Jun 13	18395011
Heterologous expression of plasmodial proteins for structural studies and functional annotation.	2008 Oct 1	18828893
PTTG: an important target gene for ovarian cancer therapy.	2008 Oct 20	19014669
Are placebo-controlled trials of creams for athlete's foot still justified?	2008 Sep	18834482
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
Fungicide-driven evolution and molecular basis of multidrug resistance in field populations of the grey mould fungus Botrytis cinerea.	2009 Dec	20019793
Label-free detection of drug-membrane association using ultraviolet-visible sum-frequency generation.	2009 Feb 4	19140762
Trichomycoses.	2009 Jul	20927231
Identification of Hedgehog signaling inhibitors with relevant human exposure by small molecule screening.	2010 Aug	20434536
Sli15(INCENP) dephosphorylation prevents mitotic checkpoint reengagement due to loss of tension at anaphase onset.	2010 Aug 10	20619650
Targeted protein depletion in Saccharomyces cerevisiae by activation of a bidirectional degron.	2010 Dec 29	21190544
Proteasome nuclear activity affects chromosome stability by controlling the turnover of Mms22, a protein important for DNA repair.	2010 Feb 19	20174551
Both interaction surfaces within cohesin's hinge domain are essential for its stable chromosomal association.	2010 Feb 23	20153193
In vitro antifungal activity of hydroxychavicol isolated from Piper betle L.	2010 Feb 3	20128889
Assay of tolnaftate in human skin samples after in vitro penetration studies using high performance liquid chromatography.	2010 Jul-Aug	20635527
Development of high-yield autofluorescent protein microarrays using hybrid cell-free expression with combined Escherichia coli S30 and wheat germ extracts.	2010 Jun 15	20546627
Current concepts in systemic and topical therapy for superficial mycoses.	2010 Mar 4	20347665
Otomycosis: Diagnosis and treatment.	2010 Mar 4	20347664
One-hit wonders of genomic instability.	2010 May 19	20482869
Breast cancer biomarker discovery in the functional genomic age: a systematic review of 42 gene expression signatures.	2010 Oct 27	21082037
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903

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.

Name

Type

Language

TOLNAFTATE

Official Name

English

TOLNAFTATE [INCI]

Common 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

SEPARIN

Brand 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