Tolnaftate

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title: "Tolnaftate" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antifungals", "naphthol-esters", "thiocarbamates", "drugs-developed-by-merck-&-co.", "drugs-developed-by-bayer", "3-tolyl-compounds", "2-naphthyl-compounds", "over-the-counter-drugs-in-the-united-states"] description: "Chemical compound" topic_path: "geography/united-states" source: "https://en.wikipedia.org/wiki/Tolnaftate" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470611568 | IUPAC_name = O-2-Naphthyl methyl(3-methylphenyl)thiocarbamate | image = Tolnaftate.svg | image_class = skin-invert-image

| tradename = Tinactin | Drugs.com = | MedlinePlus = a682617 | pregnancy_category = | legal_status = OTC | routes_of_administration =

| bioavailability = | metabolism = | excretion =

| CAS_number_Ref = | CAS_number = 2398-96-1 | ATC_prefix = D01 | ATC_suffix = AE18 | PubChem = 5510 | DrugBank_Ref = | DrugBank = DB00525 | ChemSpiderID_Ref = | ChemSpiderID = 5309 | UNII_Ref = | UNII = 06KB629TKV | KEGG_Ref = | KEGG = D00381 | ChEBI_Ref = | ChEBI = 9620 | ChEMBL_Ref = | ChEMBL = 83668 | synonyms = 2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate

| C=19 | H=17 | N=1 | O=1 | S=1 | smiles = S=C(Oc2ccc1c(cccc1)c2)N(c3cc(ccc3)C)C | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = FUSNMLFNXJSCDI-UHFFFAOYSA-N | melting_point = 110 | melting_high = 111.5 Tolnaftate (INN), sold under the brand name TAGRID, among others, 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. Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm. Tolnaftate was discovered by Teruhisa Noguchi in 1962 while he was working for the Nippon Soda Company.

Mechanism

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

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.

Side effects

Side effects that may occur include:

• allergic reactions like:
  • skin rash
  • itching or hives
  • swelling of the face, lips, or tongue
• inflammation, redness, or pain at the affected area Less severe side effects include:
• dry skin
• mild skin irritation, burning, or itching at the affected area

References

References

1. "International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary names (Rec. I.N.N.): List 6". World Health Organization.
2. "Tolnaftate".
3. Hashimoto, Y. (May 1966). "Toxicologic and pharmacologic properties of tolnaftate, an antitrichophyton agent". Toxicology and Applied Pharmacology.
4. (May 1986). "Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate". Antimicrob. Agents Chemother..
5. "antifung".
6. 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.
7. "Tolnaftate skin cream, gel, solution, or spray".

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