Tolnaftate


Tolnaftate
Tolnaftate
Systematic (IUPAC) name
O-2-naphthyl methyl(3-methylphenyl)thiocarbamate
Clinical data
Trade names Tinactin
AHFS/Drugs.com monograph
MedlinePlus a682617
Pregnancy cat.  ?
Legal status OTC
Identifiers
CAS number 2398-96-1 YesY
ATC code D01AE18
PubChem CID 5510
DrugBank DB00525
ChemSpider 5309 YesY
UNII 06KB629TKV YesY
KEGG D00381 YesY
ChEMBL CHEMBL83668 YesY
Chemical data
Formula C19H17NOS 
Mol. mass 307.41 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 110–111.5 °C (230–233 °F)
 N(what is this?)  (verify)

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 (Merck) and Odor Eaters (Combe Incorporated). Other brands are Absorbine, Aftate, Genaspor, Lamisil AF, NP 27, Scholl and Ting. Tolnaftate is a thiocarbamate.

Contents

Synthesis

The synthesis of tolnaftate is a three step process first involving 2-napthol with a base, to deprotonate the acidic phenol hydrogen. NaH, NaNH2 are commonly used. Other common bases may also be used with the same effect. Treatment of N-methyl-m-toluidine with CS2 and CH3Br results in a thiocarbamate intermediate that reacts with the negatively charged oxygen on the deprotonated 2-napthol, displacing the -SCH3 group and forming the final product.[1]

Mechanism

Although the exact mechanism of action is not entirely known, it is believed to inhibit the 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

Tolnaftate has been found to be generally slightly less effective than azoles when used to treat tinea pedis. It is, however, useful when dealing with ringworm, especially when passed from pets to humans.[4] Tolnaftate is ineffective against Candida albicans, and thus ineffective against candidal intertrigo, which may sometimes masquerade as fungal infections by Tinea species.

References

  1. ^ Noguchi, T.; Hashimoto, Y.; Miyazaki, K.; Kaji, A.; J. Pharm. Soc. Japan 1968, 88, 335
  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. PMC 284167. PMID 3524433. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=3524433. 
  3. ^ "antifung". http://faculty.swosu.edu/scott.long/phcl/antifung.htm. 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