Terbinafine

Terbinafine
Systematic (IUPAC) name
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade names Lamisil, Terboderm, Triabin
AHFS/Drugs.com monograph
MedlinePlus a699061
Pregnancy
category
  • B
Routes of
administration		 Oral and topical
Legal status
Legal status
  • Low-strength topical preparations available without prescription
Pharmacokinetic data
Bioavailability Readily absorbed: 70–90%
Protein binding >99%
Metabolism Hepatic
Biological half-life Highly variable
Identifiers
CAS Number 91161-71-6 YesY 78628-80-5
ATC code D01AE15 (WHO) D01BA02 (WHO)
PubChem CID 1549008
DrugBank DB00857 YesY
ChemSpider 1266005 YesY
UNII G7RIW8S0XP YesY
KEGG D02375 YesY
ChEBI CHEBI:9448 N
ChEMBL CHEMBL822 YesY
Chemical data
Formula C21H25N
Molar mass 291.43 g/mol
 NYesY (what is this?)  (verify)

Terbinafine hydrochloride, also known under the trade name Lamisil,[1] is an antifungal developed by Novartis and Omega Pharma. It is highly hydrophobic and tends to accumulate in hair, skin, nails, and fatty tissue.

It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.[2]

Medical uses

Terbinafine is mainly effective on the dermatophyte group of fungi.

As a 1% 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.[3]

Oral 250-mg tablets are often prescribed for the treatment of onychomycosis, a fungal nail infection, typically by a dermatophyte or Candida species. 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.[4]

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.[5]

FDA approval

Terbinafine first became available in Europe in 1991 and in the United States in 1996. 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 four and up. The antifungal granules can be sprinkled on a child's food to treat ringworm of the scalp, tinea capitis.[6]

Side effects

Many side effects and adverse drug reactions have been reported with oral terbinafine hydrochloride[7][8][9] possibly due to its extensive biodistribution and the often extended durations involved in antifungal treatment (longer than two months). A comprehensive list of adverse events associated with terbinafine use includes:

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.

Brand names

Terbinafine is sold in India as Terboderm by Omega Pharma, Lamisil in Argentina, Australia, Belgium, Brazil, Canada, Chile, Croatia, Egypt, Czech, Denmark, Estonia, Finland, France, Germany, Greece, Hungary, Iceland, Ireland, Israel, Mexico, New Zealand, Norway, Pakistan (لیمسل), Peru, Romania, Russia, Slovakia, Slovenia, South Africa, Sweden, Thailand, the United Kingdom, the United States, and Venezuela; also it is sold under the name Corbinal and Terbisil in Turkey, and Undofen in Poland. As a generic oral medication, it is sold as Sebifin, Tinasil, Terbisil, Terbicor, and Tamsil in Australia, whilst the generic topical medication is sold there as SolvEasyTinea and Tamsil.[11][12] It is also available as a generic medication in the United States, the United Kingdom, Belgium, Switzerland, Brazil and Mexico. In India, terbinafine hydrochloride is available in topical form under the brand names Triabin by Medley Pharmaceuticals, Sebifin (Ranbaxy Labs), Zimig (GSK Pharma), Tyza (Abbott Healthcare)[13] 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. Other names include Terbinaforce (Mankind Pharma) and Tafine (Deurali Janta Pharmaceuticals Pvt Ltd.) Turbo (Apex Pharmaceuticals Pvt Ltd) in Nepal. The topical form is sold as LamisilAT in the United States.

References

  1. ↑ Terbinafine - brand name list from Drugs.com
  2. ↑ "19th WHO Model List of Essential Medicines (April 2015)" (PDF). WHO. April 2015. Retrieved May 10, 2015.
  3. ↑ Markova, Tsveti (January 2002). "What is the most effective treatment for tinea pedis (athlete’s foot)?". The Journal of Family Practice (Frontline Medical Communications) 51 (1): 15–22. Retrieved 2013-11-09.
  4. ↑ "Clinical Trials Update". Genetic Engineering & Biotechnology News 29 (8): 58. 2009.
  5. ↑ Callen JP, Hughes AP, Kulp-Shorten C (September 2001). "Subacute cutaneous lupus erythematosus induced or exacerbated by terbinafine: a report of 5 cases". Arch Dermatol 137 (9): 1196–8. doi:10.1001/archderm.137.9.1196. PMID 11559217.
  6. ↑ "US FDA approves oral granules for scalp ringworm". Reuters. 2007-09-28.
  7. ↑ "Lamisil (terbinafine): Side Effects". Doublecheckmd.com. 2010-06-16. Retrieved 2013-11-09.
  8. ↑ McGuire, Stephen (2008-02-05). "Australian regulators issue warning on Novartis' Lamisil". Medical Marketing and Media. Mmm-online.com. Retrieved 2013-11-09.
  9. ↑ "Terbinafine-1 (Terbinafine Hydrochloride,Lamisil)". Drug Dosage and Side Effects. Healthline.com. 2009-02-27. Retrieved 2013-11-09.
  10. ↑ Duxbury, A J; Oliver, R J; Pemberton, M N (2000-03-25). "Case report: Persistent impairment of taste associated with terbinafine". British Dental Journal (188): 295–296. doi:10.1038/sj.bdj.4800461. Retrieved 2016-03-05. Persistent loss of taste associated with terbinafine would however appear to be extremely rare.
  11. ↑ "Terbinafine". Pharmaceutical Benefits Scheme: A-Z list. Australian Government.
  12. ↑ "PI and CMI Trade Names and Active Ingredients containing Terbinafine". Therapeutic Goods Administration. Australian Government.
  13. ↑ "Terbinafine brands in India". Brand index. DrugsUpdate India.
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