Famciclovir

• Catalog No.: Bio-0039
• CAS Number: 104227-87-4
• M. F.: C14H19N5O4
• M. W.: 321.33176

SYNONYMS

• IUPAC name: 2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate
• IUPAC Traditional name: 2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate
• Synonyms: Famvir

DATABASE IDS

• CAS Number: 104227-87-4

PROPERTIES

• Application(s): Antiviral drug
• Application(s): Used for the treatment of various herpes virus infections, most commonly for herpes zoster (shingles).
• Mechanism of Action: Guanine analogue
• Mechanism of Action: Prodrug of penciclovir with improved oral bioavailability
• Mechanism of Action: Undergoes rapid biotransformation to penciclovir
• Mechanism of Action: In cells infected with HSV-1, HSV-2 or VZV, viral thymidine kinase phosphorylates penciclovir to a monophosphate form
• Mechanism of Action: that, in turn, is converted to penciclovir triphosphate by cellular (human) kinases
• Mechanism of Action: Penciclovir triphosphate selectively inhibits viral DNA polymerase by competing with deoxyguanosine triphosphate
• Mechanism of Action: Consequently, herpes viral DNA synthesis and replication are selectively inhibited.

REFERENCES

• Eur. Pat., 1986, Beecham, 182 024; CA, 105, 133669, (synth, pmr, pharmacol)
• Vere Hodge, R.A. et al., Antimicrob. Agents Chemother., 1989, 33, 1765, (synth, pharmacokinet)
• Genn, G.R. et al., J. Med. Chem., 1989, 32, 1738, (synth)
• Winton, C.F. et al., Anal. Proc. (London), 1990, 27, 181, (hplc)
• Harnden, M.R. et al., Nucleosides Nucleotides, 1990, 9, 499, (cryst struct)
• Vere Hodge, R.A., Antiviral Chem. Chemother., 1993, 4, 67, (rev)
• Sutton, D. et al., Antiviral Res., 1993, 4, 37, (rev)
• Vere Hodge, R.A. et al., Chirality, 1993, 5, 577, (metab)
• Filer, C.W. et al., Xenobiotica, 1994, 24, 357, (metab, pharmacokinet, human)
• Cirelli, R. et al., Antiviral Res., 1996, 29, 141, (rev, pharmacol)
• Brand, B. et al., Tetrahedron, 1999, 55, 5239-5252, (synth, pmr, cmr)
• Freer, R. et al., Tetrahedron, 2000, 56, 4589-4595, (synth, pmr, cmr)