Tolnaftate

Tolnaftate (INN)[1] is a synthetic thiocarbamate used as an anti-fungal agent that may be sold without medical prescription in most jurisdictions. It is supplied as a cream, powder, spray, liquid, and liquid aerosol.[2] Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm.[2]

Tolnaftate
Clinical data
Trade namesTinactin
Other names2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate[1]
AHFS/Drugs.comMonograph
MedlinePlusa682617
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • O-2-Naphthyl methyl(3-methylphenyl)thiocarbamate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.017.516
Chemical and physical data
FormulaC19H17NOS
Molar mass307.41 g·mol−1
3D model (JSmol)
Melting point110 to 111.5 °C (230.0 to 232.7 °F)
SMILES
  • S=C(Oc2ccc1c(cccc1)c2)N(c3cc(ccc3)C)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 Y
  • Key:FUSNMLFNXJSCDI-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Mechanism

Although the exact mechanism of action is not entirely known, it is believed to inhibit squalene epoxidase,[3] an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal cell membrane) in a similar way to terbinafine.[4]

Uses

Tolnaftate has been found to be generally slightly less effective than azoles when used to treat tinea pedis (athlete's foot). It is, however, useful when dealing with ringworm, especially when passed from pets to humans.[5]

Side effects

Side effects that may occur include:[6]

Less severe side effects include:[6]

  • dry skin
  • mild skin irritation, burning, or itching at the affected area

See also

References
  1. "International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary names (Rec. I.N.N.): List 6" (PDF). World Health Organization. Retrieved 12 November 2016.
  2. "Tolnaftate". MedlinePlus,gov.
  3. Ryder NS, Frank I, Dupont MC (May 1986). "Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate". Antimicrob. Agents Chemother. 29 (5): 858–60. doi:10.1128/aac.29.5.858. PMC 284167. PMID 3524433.
  4. "antifung". Archived from the original on 2008-06-17. Retrieved 2008-07-09.
  5. Crawford F, Hart R, Bell-Syer S, Torgerson D, Young P, Russell I. Topical treatments for fungal infections of the skin and nails of the foot (Cochrane Review). In: The Cochrane Library, Issue 1, 2003. Oxford: Update Software.
  6. "Tolnaftate skin cream, gel, solution, or spray". Cleveland Clinic.
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