Terbinafine

Terbinafine, sold under the brand name Lamisil among others, is an antifungal medication used to treat pityriasis versicolor, fungal nail infections, and ringworm including jock itch and athlete's foot.[1][2][3] It is either taken by mouth or applied to the skin as a cream or ointment.[1][4] The cream and ointment are not effective for nail infections.[5]

Terbinafine
Clinical data
Trade namesLamisil, others
AHFS/Drugs.comMonograph
MedlinePlusa699061
License data
Routes of
administration
By mouth, topical
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only) / GSL
  • US: ℞-only / OTC
Pharmacokinetic data
BioavailabilityReadily absorbed: 70–90%
Protein binding>99%
Metabolismliver
Elimination half-lifeHighly variable
Identifiers
  • [(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.119.605
Chemical and physical data
FormulaC21H25N
Molar mass291.438 g·mol−1
3D model (JSmol)
  • C(#C\C=C\CN(C)Cc2cccc1ccccc12)C(C)(C)C
  • InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+ Y
  • Key:DOMXUEMWDBAQBQ-WEVVVXLNSA-N Y
 NY (what is this?)  (verify)

Common side effects when taken by mouth include nausea, diarrhea, headache, cough, rash, and elevated liver enzymes.[1] Severe side effects include liver problems and allergic reactions.[1] Liver injury is, however, unusual.[6] Use during pregnancy is not typically recommended.[1] The cream and ointment may result in itchiness but are generally well tolerated.[2] Terbinafine is in the allylamines family of medications.[1] It works by decreasing the ability of fungi to synthesize sterols.[1] It appears to result in fungal cell death.[7]

Terbinafine was discovered in 1991.[8] It is on the World Health Organization's List of Essential Medicines.[4] In 2017, it was the 307th most commonly prescribed medication in the United States, with more than one million prescriptions.[9]


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