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

基本信息

化学结构

分子式

C₁₉H₁₇NOS

分子量

307.40938

精确质量

307.10308517

电荷

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

计算属性

JChem

LogD (pH = 7.4)

5.75

LogD (pH = 5.5)

5.75

Log P

5.75

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

false

Acid pKa

0.08

极化表面积

12.47

极化性

34.34

摩尔折射率

94.92

LOG S

-7.17

数据来源

名称和标识

别名

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传统名

tolnaftate

IUPAC标准名

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

商标名

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

国际非专利药品(INN)

tolnaftatumtolnaftatetolnaftato

名称和标识

数据登录号

EC号

219-266-6

MDL号

MFCD00056611

CAS号

2398-96-1

PubChem SID

2490039416096387046505456223441027

PubChem CID

DrugBank ID

Chemspider ID

ATC码

KEGG ID

Medline Plus

美国药典/FDA物质标识码

CHEMBL

维基百科标题

PubMed文献链接

4568708215655462034766422125963570534169736220617943509341531902758563965952516584782057450672470611620635527

CHEBI ID

BindingDB数据库

Reaxys Registry

SureChEMBL数据库

Drug Central Database

3,617

专利号

WO2010037089US2010035939

BRENDA Ligand数据库

CompTox数据库

BKMS React数据库

KEGG DRUG Database

HMDB数据库

BRENDA数据库

ACToR数据库

LINCS数据库

数据登录号

化合物性质

产品相关信息

质检报告

下载链接

成盐信息

Free Base

药理学性质

法定药品分级

OTC

作用靶点

Others

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

• 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)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

tolnaftate

IUPAC标准名

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

商标名

国际非专利药品(INN)

tolnaftatumtolnaftatetolnaftato

数据登录号

EC号

219-266-6

MDL号

MFCD00056611

CAS号

2398-96-1

PubChem SID

2490039416096387046505456223441027

PubChem CID

DrugBank ID

Chemspider ID

ATC码

KEGG ID

Medline Plus

美国药典/FDA物质标识码

CHEMBL

维基百科标题

PubMed文献链接

4568708215655462034766422125963570534169736220617943509341531902758563965952516584782057450672470611620635527

CHEBI ID

BindingDB数据库

Reaxys Registry

SureChEMBL数据库

Drug Central Database

3,617

专利号

WO2010037089US2010035939

BRENDA Ligand数据库

CompTox数据库

BKMS React数据库

KEGG DRUG Database

HMDB数据库

BRENDA数据库

ACToR数据库

LINCS数据库

参考文献

PubChem文献

数据源提供

• 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)

生物活性

PubChem BioAssay

化合物性质

产品相关信息

质检报告

下载链接

成盐信息

Free Base

药理学性质

法定药品分级

OTC

作用靶点

Others

描述信息

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.

化合物信息

ID:407