Terbinafin

Strukturformel
Strukturformel von Terbinafin
Allgemeines
Freiname Terbinafin
Andere Namen
  • (E)-N-6,6-Trimethyl-N-(naphthalin-1-ylmethyl)hept-2-en-4-in-1-amin (IUPAC)
  • (E)-N-(6,6-Dimethyl-2-hepten-4-inyl)-N-methyl-1-naphthylmethylamin
Summenformel C21H25N
Externe Identifikatoren/Datenbanken
CAS-Nummer
EG-Nummer (Listennummer) 618-706-8
ECHA-InfoCard 100.119.605
PubChem 1549008
ChemSpider 1266005
DrugBank DB00857
Wikidata Q415259
Arzneistoffangaben
ATC-Code
Wirkstoffklasse

Antimykotikum

Eigenschaften
Molare Masse 291,43 g·mol−1
Aggregatzustand

fest

Schmelzpunkt

195–198 °C (Terbinafin·Hydrochlorid)[1]

Sicherheitshinweise
Bitte die Befreiung von der Kennzeichnungspflicht für Arzneimittel, Medizinprodukte, Kosmetika, Lebensmittel und Futtermittel beachten
GHS-Gefahrstoffkennzeichnung[2]

Hydrochlorid

Achtung

H- und P-Sätze H: 315​‐​319​‐​335​‐​410
P: 261​‐​273​‐​305+351+338​‐​501[2]
Toxikologische Daten
Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet.
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

Terbinafin ist ein Arzneistoff, der als Antimykotikum verwendet wird. Es handelt sich dabei um ein Allylamin-Derivat.

Anwendung

Der Wirkstoff kann topisch oder systemisch angewendet werden und wird hauptsächlich äußerlich zur Behandlung von Fußpilz und innerlich zur Behandlung von Nagelpilz (Onychomykose) verwendet. Er ist ein Standardtherapeutikum bei schwerwiegenden Onychomykosen und Dermatomykosen.

Wirkung

Terbinafin hemmt die Ergosterol-Synthese in der Pilzzellmembran. Durch die Inhibition der Squalenepoxidase blockiert Terbinafin die Umwandlung von Squalen in (S)-Squalen-2,3-epoxid, dem Vorläufer von Ergosterol. Daraus resultieren eine Squalenanreicherung und ein Ergosterolmangel der Zellmembran. Im Gegensatz zu Itraconazol, das die Umwandlung von Lanosterol in Ergosterol blockiert, wirkt Terbinafin damit früher im Syntheseweg. Letztlich blockieren beide Präparate jedoch die Bildung der Zellmembran von Pilzen, für die Ergosterol ein essentieller Bestandteil ist.

Handelsnamen

Monopräparate

Amiada (D), Amisan (A), Amykal (A), Domain (D), Fungizid-ratiopharm extra (D), Helvepidin (CH), Lamisil (D, A, CH), Mayfung (A), Myconormin (D, A, CH), Octosan (D), Pedibene (A), Tineafin (CH), Lamicosil (E), zahlreiche Generika (D, A, CH)

Literatur

  • M. Haugh, S. Helou, J. P. Boissel, B. J. Cribier: Terbinafine in fungal infections of the nails: a meta-analysis of randomized clinical trials. In: Br J Dermatol. 147, 2002, S. 118–121.
  • B. Sigurgeirsson, S. Billstein, T. Rantanen, T. Ruzicka, E. di Fonzo, B. J. Vermeer, M. J. Goodfield, E. G. Evans: L.I.ON. Study: efficacy and tolerability of continuous terbinafine (Lamisil) compared to intermittent itraconazole in the treatment of toenail onychomycosis. Lamisil vs. Itraconazole in Onychomycosis. In: Br J Dermatol. 141 Suppl, 56, 1999, S. 5–14.
  • M-H. Schmid-Wendtner: Terbinafin : systemische und topische Therapie von Pilzinfektionen. ABW-Verlag, Berlin 2006, ISBN 3-936072-44-2.

Einzelnachweise

  1. ↑ a b c d Eintrag zu Terbinafin. In: Römpp Online. Georg Thieme Verlag, abgerufen am 1. Juni 2014.
  2. ↑ a b Datenblatt Terbinafine hydrochloride bei Sigma-Aldrich, abgerufen am 23. Oktober 2016 (PDF).

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