Tolnaftate
Encyclopedia
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
.
(a key component of the fungal membrane) in a similar way to allylamines.
s when used to treat tinea pedis. It is, however, useful when dealing with ringworm, especially when passed from pets to humans. Tolnaftate is ineffective against Candida albicans
, and thus ineffective against candidal intertrigo
, which may sometimes masquerade as fungal infections by Tinea species.
Over-the-counter drug
Over-the-counter drugs are medicines that may be sold directly to a consumer without a prescription from a healthcare professional, as compared to prescription drugs, which may be sold only to consumers possessing a valid prescription...
anti-fungal agent. It may come as a cream, powder, spray, or liquid aerosol, and is used to treat jock itch
Jock itch
Tinea cruris, also known as crotch itch, crotch rot, Dhobie itch, eczema marginatum, gym itch, jock itch, and ringworm of the groin in American English is a dermatophyte fungal infection of the groin region in either sex, though more often seen in males...
, athlete's foot
Athlete's foot
Athlete's foot is a fungal infection of the skin that causes scaling, flaking, and itch of affected areas. It is caused by fungi in the genus Trichophyton and is typically transmitted in moist areas where people walk barefoot, such as showers or bathhouses...
and ringworm. It is sold under several brand names, most notably Tinactin (Merck
Merck & Co.
Merck & Co., Inc. , also known as Merck Sharp & Dohme or MSD outside the United States and Canada, is one of the largest pharmaceutical companies in the world. The Merck headquarters is located in Whitehouse Station, New Jersey, an unincorporated area in Readington Township...
) and Odor Eaters
Odor Eaters
Odor Eaters is a brand of foot-care products, especially shoe insoles and foot powder. The brand is manufactured by Blistex Inc.. Herbert Lapidus invented the namesake insoles in the early 1970s. The insoles consist of latex and activated carbon, known for its odor-neutralizing qualities.The...
(Combe Incorporated
Combe Incorporated
Combe Incorporated, based in White Plains, New York, is a privately owned personal-care company founded in 1949 by Ivan Combe. Combe products are sold in 64 countries on six continents. Ivan Combe primarily promotes the brand names instead of the company name...
). Other brands are Absorbine, Aftate, Genaspor, Lamisil AF, NP 27, Scholl and Ting. Tolnaftate is a thiocarbamate
Thiocarbamate
Thiocarbamates are a family of organosulfur compounds. There are two isomeric forms of thiocarbamate esters: O-thiocarbamates, ROCNR2, and S-thiocarbamates, RSCNR2...
.
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.Mechanism
Although the exact mechanism of action is not entirely known, it is believed to inhibit the squalene epoxidase, an important enzyme in the biosynthetic pathway of ergosterolErgosterol
Ergosterol is a sterol found in fungi, and named for ergot, a common name for the members of the fungal genus Claviceps from which ergosterol was first isolated. Ergosterol does not occur in plant or animal cells...
(a key component of the fungal membrane) in a similar way to allylamines.
Uses
Tolnaftate has been found to be generally slightly less effective than azoleAzole
An azole is a class of five-membered nitrogen heterocyclic ring compounds containing at least one other non-carbon atom of either nitrogen, sulfur, or oxygen. The parent compounds are aromatic and have two double bonds; there are successively reduced analogs with fewer...
s when used to treat tinea pedis. It is, however, useful when dealing with ringworm, especially when passed from pets to humans. Tolnaftate is ineffective against Candida albicans
Candida albicans
Candida albicans is a diploid fungus that grows both as yeast and filamentous cells and a causal agent of opportunistic oral and genital infections in humans. Systemic fungal infections including those by C...
, and thus ineffective against candidal intertrigo
Candidal intertrigo
Candidal intertrigo is an infection of the skin by Candida albicans, more specifically located between intertriginous folds of adjacent skin....
, which may sometimes masquerade as fungal infections by Tinea species.