Terbinafine

Terbinafine
Clinical data
Trade namesLamisil, Terbin, others
AHFS/Drugs.comMonograph
MedlinePlusa699061
License data
Routes of
administration		By mouth, topical
ATC code
Legal status
Legal status
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 Edit this at Wikidata
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+ checkY
  • Key:DOMXUEMWDBAQBQ-WEVVVXLNSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Terbinafine 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 should not be used for fungal nail infections.[5]

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] Oral 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 ergosterol.[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 2021, it was the 245th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[9][10]

  1. ^ a b c d e f g "Terbinafine Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  2. ^ a b "Lamisil 1% w/w Cream – Summary of Product Characteristics (SPC) – (eMC)". electronic Medicines Compendium (eMC). 17 March 2016. Archived from the original on 20 December 2016. Retrieved 17 December 2016.
  3. ^ Crawford F (July 2009). "Athlete's foot". BMJ Clinical Evidence. 2009. PMC 2907807. PMID 21696646.
  4. ^ a b World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  5. ^ Rang & Dale's Pharmacology (9th ed.). Elsevier. 2018. p. 694. ISBN 9780702074479.
  6. ^ Yan J, Wang X, Chen S (August 2014). "Systematic review of severe acute liver injury caused by terbinafine". International Journal of Clinical Pharmacy. 36 (4): 679–683. doi:10.1007/s11096-014-9969-y. PMID 24986266. S2CID 12867807.
  7. ^ "Terbinafine". www.drugbank.ca. Retrieved 2017-11-14.
  8. ^ Ravina E (2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. p. 90. ISBN 978-3-527-32669-3. Archived from the original on 2016-12-20.
  9. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  10. ^ "Terbinafine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.