Structure via PubChem · Public domain (PubChem)
terbinafine
Sign in to saveAlso known as SFO327, Terbinafina, Terbinafinum, (e)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine, (e)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine, Lamisil at, Lamisil, SF-86327
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. It is either taken by mouth or applied to the skin as a cream or ointment.
Chemical data
- Formula
- C21H25N
- Molecular weight
- 291.4 g/mol
- IUPAC name
- (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine
- SMILES
- CC(C)(C)C#C/C=C/CN(C)CC1=CC=CC2=CC=CC=C21
- InChIKey
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N
- XLogP
- 5.6
- Polar surface area
- 3.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
4,069 papers- Terbinafine-associated hepatotoxicity.The American journal of the medical sciences · 2003
- [Terbinafine-resistant dermatophytoses and onychomycosis due to Trichophyton rubrum].Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete · 2021
- Terbinafine: an update.Journal of the American Academy of Dermatology · 1997
- [Terbinafine].Annales de dermatologie et de venereologie · 1999
- Terbinafine-induced hepatotoxicity.Gastroenterologia y hepatologia · 2019
via PubMed
Wikidata facts
- Mass
- 291.1987
Show 7 more facts
- chemical formula
- C₂₁H₂₅N
- Commons category
- Terbinafine
- isomeric SMILES
- CC(C)(C)C#C/C=C/CN(C)CC1=CC=CC2=CC=CC=C21
- canonical SMILES
- CC(C)(C)C#CC=CCN(C)CC1=CC=CC2=CC=CC=C21
- World Health Organisation international non-proprietary name
- terbinafine
- defined daily dose
- 0.25
- stylized name
- LamISIL
Sources (9)
via Wikidata · CC0
~8 min read
Article
8 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- Chemistry
- History
- Society and culture
- Brand names
- References
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. It is either taken by mouth or applied to the skin as a cream or ointment.
Common side effects when taken by mouth include nausea, diarrhea, headache, cough, rash, and elevated liver enzymes. Severe side effects include liver problems and allergic reactions. Liver injury is, however, unusual. Oral use during pregnancy is not typically recommended. The cream and ointment may result in itchiness but are generally well tolerated. Terbinafine is in the allylamines family of medications. It works by decreasing the ability of fungi to synthesize ergosterol. It appears to result in fungal cell death.