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Terbinafine hydrochloride

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Terbinafine hydrochloride Basic information
Terbinafine hydrochloride Chemical Properties
  • Melting point:203-205 °C
  • Boiling point:417.9±33.0 °C(Predicted)
  • Density 1.007±0.06 g/cm3(Predicted)
  • pka6.92±0.50(Predicted)
  • CAS DataBase Reference91161-71-6(CAS DataBase Reference)
Safety Information
Terbinafine hydrochloride Usage And Synthesis
  • UsesTerbinafine (Lamisil) is a second-generation allylamine that is related to naftifine; however, it is 10 to 100 times more potent in vitro. It is fungicidal, whereas griseofulvin, ketoconazole, itraconazole, and other azole derivatives are all fungistatic. Because it is fungicidal, duration of therapy is shorter, and relapse rates are less than with other oral or topical therapies. Terbinafine acts by inhibiting squalene epoxidase and thereby decreasing synthesis of ergosterol, an essential component of fungal cell membranes. It is highly lipophilic and concentrates in the stratum corneum, sebum, and hair follicles. Slightly better cure rates are attained with b.i.d. than with daily dosing.
    Lamisil (Novartis)  Tablets
  • DefinitionChEBI: A tertiary amine that is N-methyl-1-naphthalenemethylamine in which the amino hydrogen is replaced by a 3-(tertbutylethynyl)allyl group. An antifungal agent administered orally (generally as the hydrochloride salt) for the t eatment of skin and nail infections.
  • Antimicrobial activityTerbinafine is active against a wide range of pathogenic fungi, including dermatophytes (Epidermophyton, Microsporum and Trichophyton spp.), various Candida spp., Aspergillus spp., some dimorphic fungi (Blastomyces dermatitidis, Histoplasma capsulatum and Sporothrix schenckii) and many dematiaceous fungi.
  • Acquired resistanceResistance has not been reported.
  • Pharmaceutical ApplicationsA synthetic allylamine available as the hydrochloride for oral and topical administration.
  • PharmacokineticsOral absorption: 70–80%
    Cmax 250 mg oral: c. 1 mg/L after 2 h
    Plasma half-life: c. 17 h
    Volume of distribution: 1000 L
    Plasma protein binding: >99%
    Blood concentrations increase in proportion to dosage. It is lipophilic and is rapidly and extensively distributed to body tissues. It reaches the stratum corneum by diffusion through the dermis and epidermis, and secretion in sebum. Diffusion from the nail bed is the major factor in its rapid penetration of nails. It is metabolized by the liver and the inactive metabolites are mostly excreted in the urine. The elimination half-life is prolonged in patients with hepatic or renal impairment.
  • Clinical UseTerbinafine hydrochloride can be used in Tinea pedis, tinea corporis, tinea cruris, tinea capitis, Onychomycosis caused by dermatophytes.
  • Side effectsThese include abdominal discomfort, loss of appetite, nausea, diarrhea, headache, impairment of taste, rash and urticaria. Serious skin reactions, including Stevens– Johnson syndrome, and rare hepatotoxic reactions, including jaundice, cholestasis and hepatitis, are occasionally encountered.
Terbinafine hydrochloride Preparation Products And Raw materials
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