Tolnaftate

From Wikipedia, the free encyclopedia
  (Redirected from Tinactin)
Jump to: navigation, search
Tolnaftate
Tolnaftate.svg
Clinical data
Trade names Tinactin
AHFS/Drugs.com Monograph
MedlinePlus a682617
ATC code D01AE18 (WHO)
Legal status
Legal status
  • OTC
Identifiers
Systematic (IUPAC) name: O-2-Naphthyl methyl(3-methylphenyl)thiocarbamate
Synonyms 2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate[1]
CAS Number 2398-96-1 YesY
PubChem (CID) 5510
DrugBank DB00525 YesY
ChemSpider 5309 YesY
UNII 06KB629TKV YesY
KEGG D00381 YesY
ChEBI CHEBI:9620 N
ChEMBL CHEMBL83668 YesY
Chemical and physical data
Formula C19H17NOS
Molar mass 307.41 g/mol
3D model (Jmol) Interactive image
Melting point 110 to 111.5 °C (230.0 to 232.7 °F)
 NYesY (what is this?)  (verify)

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, and liquid aerosol. Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm.

Mechanism[edit]

Although the exact mechanism of action is not entirely known, it is believed to inhibit squalene epoxidase,[2] an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal membrane) in a similar way to allylamines.[3]

Uses[edit]

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.[4]

References[edit]

  1. ^ a b "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. ^ 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 284167Freely accessible. PMID 3524433. 
  3. ^ "antifung". Retrieved 2008-07-09. 
  4. ^ 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.

External links[edit]