Tolnaftate

Tolnaftate (INN),^[1] 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.^[2] Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm.^[2] Tolnaftate was discovered by Teruhisa Noguchi in 1962 while he was working for the Nippon Soda Company.^[3]

Tolnaftate

Clinical data
Trade names	Tinactin
Other names	2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate[1]
AHFS/Drugs.com	Monograph
MedlinePlus	a682617
ATC code	D01AE18 (WHO)
Legal status
Legal status	In general: Over-the-counter (OTC)
Identifiers
IUPAC name O-2-Naphthyl methyl(3-methylphenyl)thiocarbamate
CAS Number	2398-96-1 Y
PubChem CID	5510
DrugBank	DB00525 Y
ChemSpider	5309 Y
UNII	06KB629TKV
KEGG	D00381 Y
ChEBI	CHEBI:9620 N
ChEMBL	ChEMBL83668 Y
CompTox Dashboard (EPA)	DTXSID3042477
ECHA InfoCard	100.017.516
Chemical and physical data
Formula	C19H17NOS
Molar mass	307.41 g·mol−1
3D model (JSmol)	Interactive image
Melting point	110 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,^[4] an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal cell membrane) in a similar way to terbinafine.^[5]

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.^[6]

Side effects

Side effects that may occur include:^[7]

• 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:^[7]

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

See also

• Liranaftate, a similar thiocarbamate antifungal