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2398-96-1 molecular structure
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N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide

ChemBase ID: 407
Molecular Formular: C19H17NOS
Molecular Mass: 307.40938
Monoisotopic Mass: 307.10308517
SMILES and InChIs

SMILES:
S=C(Oc1cc2c(cc1)cccc2)N(c1cc(ccc1)C)C
Canonical SMILES:
Cc1cccc(c1)N(C(=S)Oc1ccc2c(c1)cccc2)C
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

Cite this record

CBID:407 http://www.chembase.cn/molecule-407.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide
IUPAC Traditional name
tolnaftate
Brand Name
Chinofungin
Dr. Scholl's athlete's foot spray
Dermoxin
Dungistop
Focusan
Fungistop
Genaspore cream
Hi-alarzin
Hi-alazin
NP-27 Cream
NP-27 Powder
NP-27 Solution
NP-27 Spray Powder
Naphthiomate T
Naphthiomate-t
O-2-Naphthyl N,N-dimethylthiocarbanilate
O-2-Naphthyl M,N-dimethylthiocarbanilate
Phytoderm
Pitrex
Pitrex cream
Prestwick_472
Separin
Separin (TN)
Sorgoa
Sporiline
Timoped
Tinactin
Tinactin (TN)
Tinactin aerosol liquid
Tinactin aerosol powder
Tinactin antifungal deodorant powder aerosol
Tinactin cream
Tinactin jock itch aerosol powder
Tinactin jock itch cream
Tinactin jock itch spray powder
Tinactin plus aerosol powder
Tinactin plus powder
Tinactin powder
Tinactin solution
Tinaderm
Tinavet
Tinavet (veterinary)
Ting antifungal cream
Ting antifungal powder
Ting antifungal spray liquid
Ting antifungal spray powder
Ting products
Tniaderm
Tolnaftate (JP14/USP)
Tolnaftate (JP15/USP)
Tolnaftate [usan:ban:inn:jan]
Tolnaftate(USAN)
Tolnaftato [DCIT]
Tolnaftato [inn-spanish]
Tolnaftatum [inn-latin]
Tolnaphthate
Tolsanil
Tonoftal
Tritin
Zeasorb-AF
Zeasorb-AF powder
M,N-Dimethylthiocarbanilic acid O-2-naphthyl ester
o-(2-Naphthyl) methyl(3-methylphenyl)thiocarbamate
2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate
Aftate
Aftate for athlete's foot aerosol spray liquid
Aftate for athlete's foot aerosol spray powder
Aftate for athlete's foot gel
Aftate for athlete's foot sprinkle powder
Aftate for jock itch aerosol spray powder
Aftate for jock itch gel
Aftate for jock itch sprinkle powder
Carbanilic acid, N,M-dimethylthio-, O-2-naphthyl ester
Carbanilic acid, M,N-dimethylthio-, O-2-naphthyl ester
Synonyms
Tolnaftate
O-2-Naphthyl methyl(3-methylphenyl)thiocarbamate
N-Methyl-N-(3-methylphenyl)carbamothioic Acid O-2-Naphthalenyl Ester
Methyl(3-methylphenyl)carbamothioic Acid O-2-Naphthalenyl Ester
2-Naphthyl N-Methyl-N-(3-tolyl)thiocarbamate
Aftate
Chinofungin
Dermoxin
Phytoderm
Pitrex
Sch 10144
Tolnaphthate
Tolsanil
Tonoftal
Tritin
Methyl-[3-methylphenyl]-carbamothioic acid O-2-naphthyl ester
Methyl-(3-methylphenyl)carbamothioic acid O-2-naphthyl ester
Tolnaftate
CAS Number
2398-96-1
EC Number
219-266-6
MDL Number
MFCD00056611
PubChem SID
46505456
160963870
24900394
PubChem CID
5510
ATC CODE
D01AE18
CHEMBL
83668
Chemspider ID
5309
DrugBank ID
DB00525
KEGG ID
D00381
Unique Ingredient Identifier
06KB629TKV
Wikipedia Title
Tolnaftate
Medline Plus
a682617

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 5.745038  LogD (pH = 7.4) 5.7450395 
Log P 5.7450395  Molar Refractivity 94.9204 cm3
Polarizability 38.28467 Å3 Polar Surface Area 12.47 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 4.87  LOG S -5.75 
Solubility (Water) 5.46e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
7.02e-05 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] expand Show data source
Chloroform expand Show data source
DMSO expand Show data source
Apperance
White Solid expand Show data source
Melting Point
110-111.5 °C (230-232.7°F) expand Show data source
110-112°C expand Show data source
111-112°C expand Show data source
Hydrophobicity(logP)
5.1 expand Show data source
Storage Condition
2-8°C expand Show data source
Refrigerator expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
FD8891300 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
TSCA Listed
false expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
Others expand Show data source
Legal Status
OTC expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00525 external link
Item Information
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
Sigma Aldrich - T6638 external link
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.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)
  • • Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)
  • • Dresen, S., et al.: Anal. Bioanal. Chem., 396, 2425 (2009)
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PATENTS

PATENTS

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INTERNET

INTERNET

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