Terbinafine

Terbinafine

Clinical data
Trade names	Lamisil, Terboderm, others
AHFS/Drugs.com	Monograph
MedlinePlus	a699061
Pregnancy category	B
Routes of administration	by mouth and topical
ATC code	D01AE15 (WHO) D01BA02 (WHO)
Legal status
Legal status	Low-strength topical preparations available without prescription
Pharmacokinetic data
Bioavailability	Readily absorbed: 70–90%
Protein binding	>99%
Metabolism	liver
Biological half-life	Highly variable
Identifiers
IUPAC name [(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
CAS Number	91161-71-6 Y 78628-80-5
PubChem (CID)	1549008
DrugBank	DB00857 Y
ChemSpider	1266005 Y
UNII	G7RIW8S0XP Y
KEGG	D02375 Y
ChEBI	CHEBI:9448 N
ChEMBL	CHEMBL822 Y
ECHA InfoCard	100.119.605
Chemical and physical data
Formula	C21H25N
Molar mass	291.43 g/mol
3D model (Jmol)	Interactive image
SMILES C(#C\C=C\CN(C)Cc2cccc1ccccc12)C(C)(C)C
InChI 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?)

Terbinafine, sold under the brand name Lamisil among others, is an antifungal medication used to treat ringworm, pityriasis versicolor, and fungal nail infections. It is either taken by mouth or applied to the skin as a cream or ointment. The cream and ointment are not effective for nail infections.

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. 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 make sterols.

Terbinafine was discovered in 1991. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 2.20 USD for a 20 gm tube. In the United States a course of treatment costs less than 25 USD and is available over the counter.

Terbinafine is mainly effective on the dermatophyte group of fungi.

As a cream or powder, it is used topically for superficial skin infections such as jock itch (tinea cruris), athlete's foot (tinea pedis), and other types of ringworm (tinea corporis). Terbinafine cream works in about half the time required by other antifungals.