Terbinafine Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Verwenden
Terbinafine (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.
Definition
ChEBI: 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.
Indications
Terbinafine (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.
Antimicrobial activity
Terbinafine 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 resistance
Resistance has not been reported.
Pharmazeutische Anwendungen
A synthetic allylamine available as the hydrochloride for oral
and topical administration.
Pharmakokinetik
Oral absorption: 70–80%
C
max 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 Use
Terbinafine hydrochloride can be used in Tinea pedis, tinea corporis, tinea cruris, tinea capitis, Onychomycosis caused by dermatophytes.
Nebenwirkungen
These 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 Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
