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| Clinical data | |
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| Trade names | Lamisil, Terbin, others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a699061 |
| License data | |
| Routes of administration | By mouth,topical |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | Readily absorbed: 70–90% |
| Protein binding | >99% |
| Metabolism | Liver |
| Eliminationhalf-life | Highly variable |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.119.605 |
| Chemical and physical data | |
| Formula | C21H25N |
| Molar mass | 291.438 g·mol−1 |
| 3D model (JSmol) | |
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Terbinafine is anantifungal medication used to treatpityriasis versicolor,fungal nail infections, andringworm includingjock itch andathlete's foot.[1][2][3] It is eithertaken by mouth or applied to the skin as a cream or ointment.[1][4]
Common side effects when taken by mouth include nausea, diarrhea, headache, cough, rash, andelevated liver enzymes.[1] Severe side effects includeliver problems andallergic reactions.[1] Liver injury is, however, unusual.[5] Oral use duringpregnancy is not typically recommended.[1] The cream and ointment may result in itchiness but are generally well tolerated.[2] Terbinafine is in theallylamines family of medications.[1] It works by decreasing the ability of fungi to synthesizeergosterol.[1] It appears to result infungal cell death.[6]
Terbinafine was discovered in 1991.[7] It is on theWorld Health Organization's List of Essential Medicines.[4] In 2022, it was the 255th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[8][9]
Terbinafine is mainly effective onmolds of the orderOnygenales and some yeasts in the genusCandida.[citation needed]
As a cream or powder, it is usedtopically for superficial skin infections such asjock itch (tinea cruris),athlete's foot (tinea pedis), and other types ofringworm (tinea corporis).[10]
Tablets by mouth are often prescribed for the treatment ofonychomycosis, a fungal nail infection, typically by a dermatophyte orCandida species. Fungal nail infections are located deep under the nail in thecuticle to which topically applied treatments are unable to penetrate in sufficient amounts. The tablets may, rarely, causehepatotoxicity, so patients are warned of this and may be monitored withliver function tests. Alternatives to oral administration have been studied.[citation needed]
Terbinafine may induce or exacerbatesubacute cutaneous lupus erythematosus. Persons withlupus erythematosus should first discuss possible risks with their doctor before initiation of therapy.[11]
Many side effects andadverse drug reactions have been reported with oral terbinafine hydrochloride,[12][13] possibly due to its extensivebiodistribution and the often extended durations involved in antifungal treatment (longer than two months). A comprehensive list of adverse events associated with terbinafine use includes:
In 2015, physicians reported[15] that a patient with anMTHFR enzyme mutation (specifically theC677T variant) had developed an adverse reaction to terbinafine (Lamisil) (headache, fatigue, anddizziness).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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Like other allylamines, terbinafine inhibitsergosterol synthesis by inhibitingsqualene epoxidase, an enzyme that catalyzes the conversion ofsqualene tolanosterol. In fungi, lanosterol is then converted toergosterol; in humans, lanosterol becomescholesterol. However,as fungi and animals diverged around 1.1 billion years ago - there is enough difference in this enzyme that terbinafine preferentially binds fungal squalene epoxidase, making it selective for inhibiting ergosterol production in fungi without significantly affecting cholesterol production in mammals. This is thought to fatally disrupt the fungalcell membrane.[citation needed]
Terbinafine is highlylipophilic and tends to accumulate inhair, skin,nails, andfat cells.
This accumulation results in therapeutic levels of terbinafine even after 80 days following one week treatment of 250 mg/day. Different dosing schedules have been proposed such as 500 mg/day for one week or 250 mg/day for two weeks each followed by a drug-free period of two or three weeks, totaling 3 months of treatment including the drug-free periods. Such intermittent dosing schedules appear to be as effective as continuous regimens.[16]
Terbinafinehydrochloride is a white crystalline powder that is freely soluble inmethanol anddichloromethane, soluble inethanol, and slightly soluble in water.[citation needed]
Terbinafine is produced by coupling of 3,3-dimethyl-1-butyne (tert-butylacetylene) with acrolein as a key step, followed by coupling of the product of that reaction, 6,6-dimethylhept-1-en-4-yn-3-ol, with N-methyl-1-naphthalenemethanamine.[17] Multiple patents and publication to alternate syntheses are available.
Despite its name it does not containterbium.
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 now approved for use bychildren age four and up. Theantifungalgranules can be sprinkled on a child's food to treatscalp fungus.[18]
In the United States the price in 1999 was $547 for a 12-week course; this fell to $10 by 2015, after the patent had expired.[19]
{{cite web}}: CS1 maint: bot: original URL status unknown (link)Persistent loss of taste associated with terbinafine would however appear to be extremely rare.
