CAS 2398-96-1|Methyl-[3-methylphenyl]-carbamothioic acid O-2-naphthyl ester|tolnaftate|O-2-Naphthyl methyl(3-methylphenyl)thiocarbamate|N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioa...

General Information

Structure

Molecular Formula

C₁₉H₁₇NOS

Molecular Mass

307.40938

Exact Mass

307.10308517

Charge

InChI

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

InChIKey

FUSNMLFNXJSCDI-UHFFFAOYSA-N

Canonic Smiles

Cc1cccc(c1)N(C(=S)Oc1ccc2c(c1)cccc2)C

Isomeric Smiles

S=C(Oc1cc2c(cc1)cccc2)N(c1cc(ccc1)C)C

Calculated Properties

JChem

LogD (pH = 7.4)

5.75

LogD (pH = 5.5)

5.75

Log P

5.75

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

0.08

Polar Surface Area

12.47

Polarizability

34.34

Molar Refractivity

94.92

LOG S

-7.17

Data Source

Names and Identifiers

Synonyms

Methyl-[3-methylphenyl]-carbamothioic acid O-2-naphthyl esterO-2-Naphthyl methyl(3-methylphenyl)thiocarbamateTolnaftateMethyl-(3-methylphenyl)carbamothioic acid O-2-naphthyl esterTolnaftateChinofungin2-Naphthyl N-Methyl-N-(3-tolyl)thiocarbamateSch 10144PhytodermTolnaphthateTritinPitrexTolsanilTonoftalAftateDermoxinMethyl(3-methylphenyl)carbamothioic Acid O-2-Naphthalenyl EsterN-Methyl-N-(3-methylphenyl)carbamothioic Acid O-2-Naphthalenyl EsterO-2-Naphthyl m,N-dimethylthiocarbanilate2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamateTolnaphthateN-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamideMethyl (3-methylphenyl)carbamothioic acid O-2-naphthalenyl estertolnaftatem,N-Dimethylthiocarbanilic acid O-2-naphthyl ester

IUPAC Traditional name

tolnaftate

IUPAC name

N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide

Brand Name

TinactinHi-alazinTolnaftate (JP15/USP)Tolnaftate(USAN)Tinactin (TN)Ting antifungal spray powderAftate for jock itch sprinkle powderTolnaftate (JP14/USP)FungistopTolnaftato [inn-spanish]NP-27 Spray PowderAftate for jock itch gelTniadermTritinTinactin jock itch creamSporilineTing productsDr. Scholl's athlete's foot sprayO-2-Naphthyl N,N-dimethylthiocarbanilateAftatePhytodermTinactin jock itch spray powderM,N-Dimethylthiocarbanilic acid O-2-naphthyl esterNP-27 CreamSeparin (TN)Tinactin creamTinactin aerosol powderCarbanilic acid, N,M-dimethylthio-, O-2-naphthyl esterTolnaftatum [inn-latin]NP-27 PowderAftate for athlete's foot sprinkle powderNP-27 SolutionTinactin solutionPitrex creamDungistopTing antifungal spray liquidTing antifungal powderNaphthiomate-tFocusanTinavetAftate for athlete's foot gelTinactin plus powderSorgoaPrestwick_472Aftate for jock itch aerosol spray powderDermoxinGenaspore creamZeasorb-AFZeasorb-AF powderTolnaftato [DCIT]2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamateTinavet (veterinary)Tinactin antifungal deodorant powder aerosolAftate for athlete's foot aerosol spray liquidO-2-Naphthyl M,N-dimethylthiocarbanilateAftate for athlete's foot aerosol spray powderHi-alarzinTimopedTinactin jock itch aerosol powderNaphthiomate TCarbanilic acid, M,N-dimethylthio-, O-2-naphthyl esterTinactin plus aerosol powderTolsanilo-(2-Naphthyl) methyl(3-methylphenyl)thiocarbamateTinactin aerosol liquidTonoftalTinactin powderSeparinChinofunginTinadermTing antifungal creamTolnaftate [usan:ban:inn:jan]TolnaphthatePitrex

International Nonproprietary Name (INN)

tolnaftatumtolnaftatetolnaftato

Names and Identifiers

Registration numbers

EC Number

219-266-6

MDL Number

MFCD00056611

CAS Number

2398-96-1

PubChem SID

2490039416096387046505456223441027

PubChem CID

DrugBank ID

Chemspider ID

ATC CODE

KEGG ID

Medline Plus

Unique Ingredient Identifier

06KB629TKV

CHEMBL

83668CHEMBL83668

Wikipedia Title

Tolnaftate

PubMed Citation Links

4568708215655462034766422125963570534169736220617943509341531902758563965952516584782057450672470611620635527

CHEBI ID

BindingDB Database

Reaxys Registry

SureChEMBL Database

Drug Central Database

3,617

Patent number

WO2010037089US2010035939

BRENDA Ligand Database

CompTox Database

BKMS React Database

KEGG DRUG Database

HMDB Database

BRENDA Database

ACToR Database

LINCS Database

Registration numbers

Properties

Physical Property

Product Information

Certificate of Analysis

Download link

Salt Data

Free Base

Pharmacology Properties

Legal Status

OTC

Target

Others

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00525

Drug Groups

approved

Description

Tolnaftate is a synthetic over-the-counter anti-fungal agent. It may come as a cream, powder, spray, or liquid aerosol, and is used to treat jock itch, athlete's foot and ringworm. It is sold under several brand names, most notably Tinactin (Schering-Plough Corporation) and Odor Eaters (Combe Incorporated). Other brands are Absorbine, Aftate, Desenex, Genaspor, NP 27, and Ting.

Indication

Tolnaftate topical is used to treat skin infections such as athlete's foot, jock itch, and ringworm infections. Tolnaftate is also used, along with other antifungals, to treat infections of the nails, scalp, palms, and soles of the feet. The powder and powder aerosol may be used to prevent athlete's foot.

Pharmacology

Tolnaftate is a synthetic over-the-counter anti-fungal agent.

Toxicity

Oral rat LD50: 891 mg/kg. Inhalation rat LC50: > 900 mg/m3/1hr. Irritation: skin rabbit: 500 mg/24H mild. Eye rabbit: 100 mg severe. Investigated a mutagen and reproductive effector.

Affected Organisms

Yeast and other fungi

References

• Barrett-Bee K, Dixon G: Ergosterol biosynthesis inhibition: a target for antifungal agents. Acta Biochim Pol. 1995;42(4):465-79. [Pubmed]

• Ryder NS, Frank I, Dupont MC: Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate. Antimicrob Agents Chemother. 1986 May;29(5):858-60. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

Crystalline

T6638

Application
Tolnaftate is used to study the mechanism of ergosterol (sterol) biosynthesis at the rate-limiting step of squalene epoxidase inhibition. Tolnaftate is clinically used to treat cutaneous infections such as athlete′s foot, jock itch, and ringworm1. It also has been used as a comparator compound for antifungal efficiency studies2.
Biochem/physiol Actions
Tolnaftate prevents ergosterol biosynthesis by inhibiting squalene epoxidase. It has also been reported to distort the hyphae and to stunt mycelial growth in susceptible organisms1. Tolnaftate inhibits biosynthesis of aflatoxin.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T6638.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

T535400

Antifungal.

ChEBI

CHEBI:9620

A monothiocarbamic ester that is the methyl(3-tolyl)carbamothioate ester of 2-naphthol. A synthetic anti-fungal agent used to treat jock itch, athlete's foot and ringworm.

Molecule Details

References

PubChem Literature

From Data Sources

• Ryder NS, Frank I, Dupont MC: Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate. Antimicrob Agents Chemother. 1986 May;29(5):858-60. Pubmed

• Barrett-Bee K, Dixon G: Ergosterol biosynthesis inhibition: a target for antifungal agents. Acta Biochim Pol. 1995;42(4):465-79. Pubmed

• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)

• Dresen, S., et al.: Anal. Bioanal. Chem., 396, 2425 (2009)

• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

tolnaftate

IUPAC name

N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide

Brand Name

International Nonproprietary Name (INN)

tolnaftatumtolnaftatetolnaftato

Registration numbers

EC Number

219-266-6

MDL Number

MFCD00056611

CAS Number

2398-96-1

PubChem SID

2490039416096387046505456223441027

PubChem CID

DrugBank ID

Chemspider ID

ATC CODE

KEGG ID

Medline Plus

Unique Ingredient Identifier

06KB629TKV

CHEMBL

83668CHEMBL83668

Wikipedia Title

Tolnaftate

PubMed Citation Links

4568708215655462034766422125963570534169736220617943509341531902758563965952516584782057450672470611620635527

CHEBI ID

BindingDB Database

Reaxys Registry

SureChEMBL Database

Drug Central Database

3,617

Patent number

WO2010037089US2010035939

BRENDA Ligand Database

CompTox Database

BKMS React Database

KEGG DRUG Database

HMDB Database

BRENDA Database

ACToR Database

LINCS Database

Properties

Physical Property

Product Information

Certificate of Analysis

Download link

Salt Data

Free Base

Pharmacology Properties

Legal Status

OTC

Target

Others

References

PubChem Literature

From Data Sources

• Ryder NS, Frank I, Dupont MC: Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate. Antimicrob Agents Chemother. 1986 May;29(5):858-60. Pubmed

• Barrett-Bee K, Dixon G: Ergosterol biosynthesis inhibition: a target for antifungal agents. Acta Biochim Pol. 1995;42(4):465-79. Pubmed

• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)

• Dresen, S., et al.: Anal. Bioanal. Chem., 396, 2425 (2009)

• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)

Bioactivity

PubChem BioAssay

Molecule Details

DrugBank

DB00525

Drug Groups

approved

Description

Indication

Pharmacology

Tolnaftate is a synthetic over-the-counter anti-fungal agent.

Toxicity

Oral rat LD50: 891 mg/kg. Inhalation rat LC50: > 900 mg/m3/1hr. Irritation: skin rabbit: 500 mg/24H mild. Eye rabbit: 100 mg severe. Investigated a mutagen and reproductive effector.

Affected Organisms

Yeast and other fungi

References

• Barrett-Bee K, Dixon G: Ergosterol biosynthesis inhibition: a target for antifungal agents. Acta Biochim Pol. 1995;42(4):465-79. [Pubmed]

• Ryder NS, Frank I, Dupont MC: Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate. Antimicrob Agents Chemother. 1986 May;29(5):858-60. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

Crystalline

T6638

T535400

Antifungal.

ChEBI

CHEBI:9620

A monothiocarbamic ester that is the methyl(3-tolyl)carbamothioate ester of 2-naphthol. A synthetic anti-fungal agent used to treat jock itch, athlete's foot and ringworm.

Molecule

ID:407