Tolnaftate

Tolnaftate
Clinical data
Trade names	Tinactin
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 ;
PubChem CID	5510;
DrugBank	DB00525 ;
ChemSpider	5309 ;
UNII	06KB629TKV;
KEGG	D00381 ;
ChEMBL	ChEMBL83668 ;
CompTox Dashboard (EPA)	DTXSID3042477 ;
ECHA InfoCard	100.017.516
Chemical and physical data
Formula	C19H17NOS
Molar mass	307.41 g/mol 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 ; Key:FUSNMLFNXJSCDI-UHFFFAOYSA-N ;
	(verify)

Tolnaftate 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. It is sold under several brand names, including Absorbine, Aftate, Genaspor, Lamisil AF, NP 27, Odor Eaters (Combe Incorporated), Scholl, Tinactin (Merck), Tinaderm, and Ting.

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 (athlete's foot). 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 dermatophytic fungi that are typically the cause of tinea.

References

^ Noguchi, T.; Hashimoto, Y.; Miyazaki, K.; Kaji, A.; J. Pharm. Soc. Japan 1968, 88, 335
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ "antifung". Retrieved 2008-07-09.
^ 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

Medline's entry for tolnaftate

[1] Noguchi, T.; Hashimoto, Y.; Miyazaki, K.; Kaji, A.; J. Pharm. Soc. Japan 1968, 88, 335

[pmid3524433-2] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[urlantifung-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.

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