Terbinafine

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Terbinafine
Systematic (IUPAC) name
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade namesLamisilat
AHFS/Drugs.commonograph
MedlinePlusa699061
Pregnancy cat.B
Legal status ?
RoutesOral, topical
Pharmacokinetic data
BioavailabilityReadily absorbed: 70–90%
Protein binding>99%
MetabolismHepatic
Half-lifeHighly variable
Identifiers
CAS number91161-71-6 YesY 78628-80-5
ATC codeD01AE15 D01BA02
PubChemCID 1549008
DrugBankDB00857
ChemSpider1266005 YesY
UNIIG7RIW8S0XP YesY
KEGGD02375 YesY
ChEMBLCHEMBL822 YesY
Chemical data
FormulaC21H25N 
Mol. mass291.43 g/mol
 YesY (what is this?)  (verify)
 
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Terbinafine
Systematic (IUPAC) name
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade namesLamisilat
AHFS/Drugs.commonograph
MedlinePlusa699061
Pregnancy cat.B
Legal status ?
RoutesOral, topical
Pharmacokinetic data
BioavailabilityReadily absorbed: 70–90%
Protein binding>99%
MetabolismHepatic
Half-lifeHighly variable
Identifiers
CAS number91161-71-6 YesY 78628-80-5
ATC codeD01AE15 D01BA02
PubChemCID 1549008
DrugBankDB00857
ChemSpider1266005 YesY
UNIIG7RIW8S0XP YesY
KEGGD02375 YesY
ChEMBLCHEMBL822 YesY
Chemical data
FormulaC21H25N 
Mol. mass291.43 g/mol
 YesY (what is this?)  (verify)

Terbinafine hydrochloride is a synthetic allylamine antifungal from Novartis. It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues.

It is sold by the name Lamisil in Argentina, Australia, Belgium, Brazil, Canada, Chile, Egypt, Czech, Finland, France, Germany, Greece, Hungary, Iceland, Ireland, Israel, Mexico, New Zealand, Norway, Pakistan (لیمسل), Peru, Romania, Russia, Slovakia, Slovenia, South Africa, Sweden, United Kingdom, United States and Venezuela, also sold under the name Corbinal and Terbisil in Turkey and under the name "undofen cream" in Poland. As a generic it is sold under the name Zabel in Australia. It is also available as a generic medication in the United States, United Kingdom, Belgium, Switzerland and Brazil.

In India, Terbinafine hydrochloride is available in topical form under the brand name Sebifin (Ranbaxy Labs), Zimig (GSK Pharma) and mycoCeaze (Progreś Laboratories).

MycoVa, developed by Apricus Biosciences, is a topical nail solution of terbinafine and DDAIP which has completed three Phase III studies for the treatment of onychomycosis.

Contents

Pharmacology

Generic terbinafine hydrochloride pills

Terbinafine hydrochloride is a white fine crystalline powder that is freely soluble in methanol and dichloromethane, soluble in ethanol, and slightly soluble in water.

Like other allylamines, terbinafine inhibits ergosterol synthesis by inhibiting squalene epoxidase, an enzyme that is part of the fungal cell membrane synthesis pathway. Because terbinafine prevents conversion of squalene to lanosterol, ergosterol cannot be synthesized. This is thought to change cell membrane permeability, causing fungal cell lysis.

Indications

Terbinafine is mainly effective on the dermatophytes group of fungi.

As a 1% cream or powder it is used for superficial skin infections such as jock itch (Tinea cruris), athlete's foot (Tinea pedis) and other types of ringworm (Tinea corporis). Studies have shown that terbinafine cream works in about half the time required by other antifungals[1].

Oral 250 mg tablets are often prescribed for the treatment of onychomycosis of the toenail or fingernail due to the dermatophyte Tinea unguium. Fungal nail infections are located deep under the nail in the cuticle to which topically applied treatments are unable to penetrate in sufficient amounts. The tablets may, rarely, cause hepatotoxicity, so patients are warned of this and may be monitored with liver function tests. Alternatives to oral administration have been studied. In 2009, results from a clinical study of a new formulation (terbinafine in Transfersomes, referred to as TDT-067) for topical treatment of onychomycosis were reported by Celtic Pharma.[2]

It has been found that terbinafine hydrochloride may induce or exacerbate subacute cutaneous lupus erythematosus. Persons with lupus erythematosus should first discuss possible risks with their doctor before initiation of therapy.[3]

FDA approval

The U.S. Food and Drug Administration has approved the first generic versions of prescription Lamisil (terbinafine hydrochloride) tablets. The remaining patent or exclusivity for Lamisil expired on June 30, 2007.

On September 28, 2007, the FDA stated that Lamisil (terbinafine hydrochloride, by Novartis AG) is a new treatment approved for use by children age 4 and up. The antifungal granules can be sprinkled on a child's food to treat ringworm of the scalp, Tinea capitis.[4]

Side effects

Many side effects and adverse drug reactions have been reported with terbinafine[5][6][7] possibly due to its extensive biodistribution and the often extended durations involved in anti-fungal treatment ( > 2 months ). The following is a comprehensive list of adverse events that are associated with terbinafine use:

References