Terbinafine
You don't need to be Editor-In-Chief to add or edit content to WikiDoc. You can begin to add to or edit text on this WikiDoc page by clicking on the edit button at the top of this page. Next enter or edit the information that you would like to appear here. Once you are done editing, scroll down and click the Save page button at the bottom of the page.
| |
| Terbinafine
| |
| Systematic (IUPAC) name | |
| N,6,6-trimethyl-N-(naphthalen-1-ylmethyl) hept-2-en-4-yn-1-amine | |
| Identifiers | |
| CAS number | |
| ATC code | D01 D01BA02 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C21H25N |
| Mol. mass | 291.43 g/mol |
| Pharmacokinetic data | |
| Bioavailability | Readily absorbed |
| Protein binding | >99% |
| Metabolism | Hepatic |
| Half life | 36 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
B |
| Legal status | |
| Routes | Oral topical |
|
WikiDoc Resources for Terbinafine | |
|
Articles | |
|---|---|
|
Most recent articles on Terbinafine Most cited articles on Terbinafine | |
|
Media | |
|
Powerpoint slides on Terbinafine | |
|
Evidence Based Medicine | |
|
Clinical Trials | |
|
Ongoing Trials on Terbinafine at Clinical Trials.gov Clinical Trials on Terbinafine at Google
| |
|
Guidelines / Policies / Govt | |
|
US National Guidelines Clearinghouse on Terbinafine
| |
|
Books | |
|
News | |
|
Commentary | |
|
Definitions | |
|
Patient Resources / Community | |
|
Patient resources on Terbinafine Discussion groups on Terbinafine Patient Handouts on Terbinafine Directions to Hospitals Treating Terbinafine Risk calculators and risk factors for Terbinafine
| |
|
Healthcare Provider Resources | |
|
Causes & Risk Factors for Terbinafine | |
|
Continuing Medical Education (CME) | |
|
International | |
|
| |
|
Businness | |
|
Experimental / Informatics | |
Please Take Over This Page and Apply to be Editor-In-Chief for this topic: There can be one or more than one Editor-In-Chief. You may also apply to be an Associate Editor-In-Chief of one of the subtopics below. Please mail us [1] to indicate your interest in serving either as an Editor-In-Chief of the entire topic or as an Associate Editor-In-Chief for a subtopic. Please be sure to attach your CV and or biographical sketch.
Terbinafine hydrochloride (Lamisil in UK, US, France, Canada, Romania and Hungary, also sold under the name Terbisil) is a synthetic allylamine antifungal. It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. As a generic it is sold under the name Zabel in Australia. It is now also available as a generic in the U.S.
Pharmacology
Terbinafine hydrochloride is a white fine crystalline powder that is freely soluble in methanol and methylene chloride, 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 wall synthesis pathway.
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.
Oral 250mg 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. Alcohol consumption should also be avoided while taking terbinafine.
Specific US issues
Many health insurance companies consider these infections to be a cosmetic problem, and either do not cover the cost of the months-long course of Lamisil, which can run into the thousands of dollars, or recommend use of less expensive alternatives like fluconazole.
FDA approval
The FDA 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 U.S. Food and Drug Administration stated that Lamisil (terbinafine hydrochloride, by Novartis AG) is a new treatment approved for use by children aged 4 up. The antifungal granules that can be sprinkled on a child's food to treat ringworm of the scalp, Tinea capitis. [1]
References
Antifungals (D01 and J02) | |
|---|---|
| Antibiotics | Griseofulvin • polyene antimycotics (Natamycin, Nystatin) |
| Topical azoles | imidazoles (Bifonazole, Clomidazole, Clotrimazole, Econazole, Fenticonazole, Ketoconazole, Isoconazole, Miconazole, Oxiconazole, Sertaconazole, Sulconazole, Tioconazole) • triazoles (Fluconazole) • benzimidazole (Thiabendazole) |
| Other topicals | Ciclopirox • Ethylparaben • Flucytosine • Salicylic acid • Selenium sulfide • Tolnaftate • Undecylenic acid • allylamines (Amorolfine, Butenafine, Naftifine, Terbinafine) |
| For systemic use | Griseofulvin • allylamine (Terbinafine) • polyene antimycotic (Amphotericin B) • triazoles (Itraconazole, Posaconazole, Voriconazole) • echinocandins (Anidulafungin, Caspofungin, Micafungin) |
| Other | Tea tree oil • citronella oil • lemon grass • orange oil • patchouli • lemon myrtle |
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
