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Tolnaftate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Tolnaftate
Clinical data
Trade namesTinactin
Other names2-NaphthylN-methyl-N-(3-tolyl)thionocarbamate[1]
AHFS/Drugs.comMonograph
MedlinePlusa682617
ATC code
Legal status
Legal status
Identifiers
  • O-2-Naphthyl methyl(3-methylphenyl)thiocarbamate
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.017.516Edit this at Wikidata
Chemical and physical data
FormulaC19H17NOS
Molar mass307.41 g·mol−1
3D model (JSmol)
Melting point110 to 111.5 °C (230.0 to 232.7 °F)
  • S=C(Oc2ccc1c(cccc1)c2)N(c3cc(ccc3)C)C
  • 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 checkY
  • Key:FUSNMLFNXJSCDI-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tolnaftate (INN),[1] sold under the brand nameTAGRID, among others, is a syntheticthiocarbamate used as ananti-fungal agent that may be soldwithout medical prescription in most jurisdictions. It is supplied as a cream, powder, spray, liquid, andliquid aerosol.[2] Tolnaftate is used to treat fungal conditions such asjock itch,athlete's foot andringworm.[2]

Mechanism

[edit]

Although the exact mechanism of action is not entirely known, it is believed to inhibitsqualene epoxidase,[3] an important enzyme in the biosynthetic pathway ofergosterol (a key component of the fungal cell membrane) in a similar way toterbinafine.[4]

Uses

[edit]

Tolnaftate has been found to be generally slightly less effective thanazoles when used to treattinea pedis (athlete's foot). It is, however, useful when dealing withringworm, especially when passed from pets to humans.[5]

Side effects

[edit]

Side effects that may occur include:[6]

Less severe side effects include:[6]

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

See also

[edit]

References

[edit]
  1. ^ab"International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary names (Rec. I.N.N.): List 6"(PDF). World Health Organization. Retrieved12 November 2016.
  2. ^ab"Tolnaftate".MedlinePlus,gov.
  3. ^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 284167.PMID 3524433.
  4. ^"antifung". Archived fromthe original on 2008-06-17. Retrieved2008-07-09.
  5. ^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.
  6. ^ab"Tolnaftate skin cream, gel, solution, or spray".Cleveland Clinic.

External links

[edit]
Wall/
membrane
Ergosterol
inhibitors
Azoles (lanosterol 14α-
demethylase
inhibitors)
Imidazoles
Triazoles
Thiazoles
Polyene antimycotics
(ergosterol binding)
Squalene monooxygenase
inhibitors
Allylamines
Benzylamines
Others
β-glucan synthase
inhibitors
Intracellular
Pyrimidine analogues/
thymidylate synthase inhibitors
Mitotic inhibitors
Aminoacyl tRNA synthetase inhibitors
Others
CARTooltip Constitutive androstane receptor
PXRTooltip Pregnane X receptor
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