Tolnaftate

• Catalog No.: DB00525
• CAS Number: 2398-96-1
• M. F.: C19H17NOS
• M. W.: 307.40938

SYNONYMS

• IUPAC name: N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide
• IUPAC Traditional name: tolnaftate
• Brand Name: Tolsanil; Tinavet (veterinary); Sporiline; Carbanilic acid, N,M-dimethylthio-, O-2-naphthyl ester; Aftate; Chinofungin; Dermoxin; Fungistop; NP-27 Solution; Naphthiomate T; Naphthiomate-t; O-2-Naphthyl M,N-dimethylthiocarbanilate; Tinactin plus aerosol powder; Tinactin solution; Tonoftal; Tritin; Carbanilic acid, M,N-dimethylthio-, O-2-naphthyl ester; Focusan; Hi-alazin; NP-27 Cream; NP-27 Powder; O-2-Naphthyl N,N-dimethylthiocarbanilate; Phytoderm; Separin; Timoped; Tinactin; Tinactin aerosol powder; Tinactin cream; Tinactin jock itch spray powder; Tinactin plus powder; Tinactin powder; Ting antifungal powder; Tolnaftate (JP14/USP); Tolnaftate (JP15/USP); Tolnaftate(USAN); Tolnaftato [DCIT]; M,N-Dimethylthiocarbanilic acid O-2-naphthyl ester; Aftate for athlete's foot aerosol spray liquid; Aftate for athlete's foot aerosol spray powder; Aftate for jock itch gel; Dr. Scholl's athlete's foot spray; Dungistop; Genaspore cream; Hi-alarzin; NP-27 Spray Powder; Pitrex; Pitrex cream; Prestwick_472; Separin (TN); Sorgoa; Tinactin (TN); Tinactin aerosol liquid; Tinactin antifungal deodorant powder aerosol; Tinactin jock itch aerosol powder; Tinactin jock itch cream; Tinaderm; Tinavet; Ting antifungal cream; Ting antifungal spray liquid; Ting antifungal spray powder; Ting products; Tniaderm; Tolnaftate [usan:ban:inn:jan]; Tolnaftato [inn-spanish]; Tolnaftatum [inn-latin]; Tolnaphthate; Zeasorb-AF; Zeasorb-AF powder; o-(2-Naphthyl) methyl(3-methylphenyl)thiocarbamate; 2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate; Aftate for athlete's foot gel; Aftate for athlete's foot sprinkle powder; Aftate for jock itch aerosol spray powder; Aftate for jock itch sprinkle powder

DATABASE IDS

• PubChem CID: 5510
• PubChem SID: 46505456
• CAS Number: 2398-96-1

PROPERTIES

• Hydrophobicity(logP): 5.1
• Solubility: 7.02e-05 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]

DETAILS

Description (English)

• 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

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