Famciclovir

Strukturformel
Allgemeines
Freiname Famciclovir
Andere Namen
  • 2-[2-(2-Amino-9H-purin-9-yl)ethyl]-1,3-propandiyl-diacetat
  • [2-(Acetyloxymethyl)-4-(2-aminopurin-9-yl)butyl]acetat (IUPAC)
Summenformel C14H19N5O4
Externe Identifikatoren/Datenbanken
CAS-Nummer 104227-87-4
EG-Nummer (Listennummer) 630-411-6
ECHA-InfoCard 100.158.713
PubChem 3324
ChemSpider 3207
DrugBank DB00426
Wikidata Q420186
Arzneistoffangaben
ATC-Code
Wirkstoffklasse

Virostatikum

Eigenschaften
Molare Masse 321,33 g·mol−1
Aggregatzustand

fest

Schmelzpunkt

102–104 °C[1]

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

H- und P-Sätze H: keine H-Sätze
P: keine P-Sätze[2]
Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet.
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

Famciclovir ist ein Analogon der Nukleinbase 2-Aminopurin und wird als Virostatikum bei Infektionen und Reaktivierungen von Herpes-simplex-Viren (HSV-1 und -2) und Varizella-Zoster-Virus (VZV) eingesetzt.

Chemie

Famciclovir ist das Diacetyl-Derivat von Penciclovir, welches nach oraler Einnahme keine ausreichende Bioverfügbarkeit erzielen konnte. Das machte die Entwicklung einer Substanz mit besserer Pharmakokinetik erforderlich.

Pharmakologie

Famciclovir ist ein Prodrug von Penciclovir, das nach oraler Einnahme metabolisiert wird und dabei durch Deacetylierung sowie anschließender Oxidation zu Penciclovir umgewandelt wird.

Anwendung

Der Wirkstoff wird als Rezidivanz zur Behandlung des Herpes genitalis bzw. zur Frühbehandlung eines Herpes zoster („Gürtelrose“) eingesetzt. In Kombination mit Lamivudin wurde Famciclovir in Studien als Ersatz zur Interferon-Kombinationstherapie auch bei einer chronischen Infektion mit Hepatitis B angewendet.[3] Dies ist seit der Verfügbarkeit spezifischer Virustatika gegen das Hepatitis-B-Virus obsolet.

Handelsnamen

Monopräparate
Famvir (D, A, CH) sowie ein Generikum (A)

  • Eintrag zu Famciclovir in der Human Metabolome Database (HMDB), abgerufen am 29. Oktober 2013.

Einzelnachweise

  1. ↑ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14. Auflage. 2006, ISBN 0-911910-00-X, S. 670.
  2. ↑ a b Datenblatt Famciclovir, United States Pharmacopeia (USP) Reference Standard bei Sigma-Aldrich, abgerufen am 3. Januar 2023 (PDF).
  3. ↑ C. Trépo et al.: Famciclovir in chronic hepatitis B: results of a dose-finding study. In: Journal of Hepatology, 2000, 32(6), S. 1011–1018; PMID 10898322

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