Substance
ID:449146
Names and Identifiers
IUPAC name
2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate
Synonyms
FamvirFamciclovir
IUPAC Traditional name
2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate
Registration numbers
CAS Number
Properties
Pharmacology Properties
Mechanism of Action
Undergoes rapid biotransformation to penciclovir
that, in turn, is converted to penciclovir triphosphate by cellular (human) kinases
Consequently, herpes viral DNA synthesis and replication are selectively inhibited.
Guanine analogue
Prodrug of penciclovir with improved oral bioavailability
Penciclovir triphosphate selectively inhibits viral DNA polymerase by competing with deoxyguanosine triphosphate
In cells infected with HSV-1, HSV-2 or VZV, viral thymidine kinase phosphorylates penciclovir to a monophosphate form
Product Information
Application(s)
Antiviral drug
Used for the treatment of various herpes virus infections, most commonly for herpes zoster (shingles).
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• Vere Hodge, R.A. et al., Antimicrob. Agents Chemother., 1989, 33, 1765, (synth, pharmacokinet)
• Cirelli, R. et al., Antiviral Res., 1996, 29, 141, (rev, pharmacol)
• Vere Hodge, R.A., Antiviral Chem. Chemother., 1993, 4, 67, (rev)
• Genn, G.R. et al., J. Med. Chem., 1989, 32, 1738, (synth)
• Harnden, M.R. et al., Nucleosides Nucleotides, 1990, 9, 499, (cryst struct)
• Vere Hodge, R.A. et al., Chirality, 1993, 5, 577, (metab)
• Filer, C.W. et al., Xenobiotica, 1994, 24, 357, (metab, pharmacokinet, human)
• Brand, B. et al., Tetrahedron, 1999, 55, 5239-5252, (synth, pmr, cmr)
• Eur. Pat., 1986, Beecham, 182 024; CA, 105, 133669, (synth, pmr, pharmacol)
• Winton, C.F. et al., Anal. Proc. (London), 1990, 27, 181, (hplc)
• Freer, R. et al., Tetrahedron, 2000, 56, 4589-4595, (synth, pmr, cmr)
• Sutton, D. et al., Antiviral Res., 1993, 4, 37, (rev)