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Terbinafine, sold under the brand name Lamisil among others, an antifungal medication used to treat pityriasis versicolor, fungal nail infections, and ringworm including jock itch and athlete’s foot.
Common side effects when taken by mouth include nausea, diarrhea, headache, cough, rash, and elevated liver enzymes.
Terbinafine was discovered in 1991.
1 Medical uses
1.1 FDA approval
2 Side effects
4 Brand names
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.
Tablets by mouth 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 by mouth administration have been studied.
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.
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 terbinafine 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.
Many side effects and adverse drug reactions have been reported with oral terbinafine hydrochloride 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:
Gastrointestinal problems: Diarrhea, constipation, nausea, fullness, abdominal pain, indigestion, dyspepsia, gastritis, cholestasis, flatulence, altered stool colour, abdominal muscular pain
Central nervous system or neurological problems: Headaches, dizziness, vertigo, light-headedness, decreased concentration levels, paraesthesia (pins and needles)
Hepatic problems: Raised liver enzyme levels, liver inflammation ( hepatitis ), liver damage, liver failure
Immune system problems: Decreased white blood cell counts including pancytopenia, leukopenia, lymphopenia, thrombocytopenia, agranulocytosis, and neutropenia, autoimmune reactions such as lupus erythematosus
Psychological problems: Depression, anxiety, insomnia, increased or unusual dream activity, malaise
Sensory problems: Complete loss of taste ( ageusia ), decreased taste ( hypogeusia ) and distorted taste ( dysgeusia ), often involving a metallic taste sensation and dry mouth, visual disturbances including blurred vision, green vision and double vision. In extremely rare cases, the loss or impairment of taste is permanent
Skin problems: Rashes, hives ( urticaria ), skin irritation, itching, jaundice, Stevens–Johnson syndrome
Other side effects: Fatigue, increased heart rate ( tachycardia ), hair loss ( alopecia ), decreased red blood cell count ( anemia ), muscle pain ( myalgia ), joint pain ( arthralgia )
In 2015 physicians reported that a patient with an MTHFR enzyme mutation (specifically the C677T variant) had developed an adverse reaction to Lamisil (headache, fatigue, and dizziness). Genetic testing revealed the MTHFR C677T mutation. It was noted that Lamisil interferes with the methylation cycle and that this can cause side effects in individuals with the MTHFR C677T mutation.
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Terbinafine hydrochloride is a white fine crystalline powder that is freely soluble in methanol and dichloromethane, soluble in ethanol, and slightly soluble in water. It is highly hydrophobic and tends to accumulate in hair, skin, nails, and fatty tissue.
Like other allylamines, terbinafine inhibits ergosterol synthesis by inhibiting squalene epoxidase, an enzyme that catalyzes the conversion of squalene to lanosterol. In fungi, lanosterol is then converted to ergosterol ; in humans, lanosterol becomes cholesterol. However, there is sufficient genetic divergence between fungal and human squalene epoxidases that terbinafine preferentially binds fungal squalene epoxidase, making it selective for inhibiting ergosterol production in fungi without significantly affecting cholesterol production in humans. This is thought to change cell membrane permeability, causing fungal cell lysis.
Terbinafine is sold in India as Terboderm by Omega Pharma and Tyza (Abbott Healthcare), 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 (Sun Pharma), 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. 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.
Terbinafine is produced from metathesis of 1,3-dichloropropene and neohexene followed by reaction with N -methyl-1-naphthalenemethanamine.
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