Naftifine

Naftifine
Systematic (IUPAC) name
(2E)-N-methyl-N-(1-naphthylmethyl)-3-phenylprop-2-en-1-amine
Clinical data
Trade names Naftin
AHFS/Drugs.com monograph
MedlinePlus a688020
Identifiers
65472-88-0 Yes
D01AE22
PubChem CID 47641
DrugBank DB00735 Yes
ChemSpider 66071 
UNII 4FB1TON47A 
ChEBI CHEBI:7451 
ChEMBL CHEMBL626 
Chemical data
Formula C21H21N
287.398 g/mol
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Naftifine (brand name Naftin) is an allylamine antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis (fungal infections).

Its precise mechanism of action is unknown, but may involve selectively blocking sterol biosynthesis via inhibition of the squalene 2,3-epoxidase enzyme.[1][2] The half-life is approximately 2–3 days.[2] The metabolites are excreted in the urine and feces.[3]

Synthesis

Naftifine synthesis: DE 2716943 DE 2809211 BE 853976 U.S. Patent 4,282,251 [4]

References

  1. ↑ Robertson Dirk B, Maibach Howard I, "Chapter 61. Dermatologic Pharmacology" (Chapter). Bertram G. Katzung, Susan B. Masters, Anthony J. Trevor: Basic & Clinical Pharmacology, 11e: http://www.accesspharmacy.com/content.aspx?aID=4517257.
  2. ↑ 2.0 2.1 Micromedex DRUGDEX Drug Point: Naftifine Hydrochloride. Accessed at www.thomsonhc.com/../BeginWith#secN10184, February 18, 2010.
  3. ↑ AccessPharmacy: Drug Monographs: Naftifine. Accessed at http://www.accesspharmacy.com/drugContentPopup.aspx?mid=6620&section=10, February 18, 2010.
  4. ↑ Loibner, H.; Pruckner, A.; Stütz, A. (1984). "Reduktive methylierung primärer und sekundärer amine mit hilfe von formaldehyd und salzen der phosphorigen säure". Tetrahedron Letters 25 (24): 2535. doi:10.1016/S0040-4039(01)81224-7.