Aciclovir

• Catalog No.: Bio-0206
• CAS Number: 59277-89-3
• M. F.: C8H11N5O3
• M. W.: 225.20464

SYNONYMS

• IUPAC name: 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one
• Synonyms: Virasorb; Supraviran; Milavir; Acycloguanosine; Cycloviran; Activir; Avirax; Geavir; Herpetad; Soothelip; Mirolex; Virovir; Zyclir; Zovirax; Acyclovir

DATABASE IDS

• CAS Number: 59277-89-3

PROPERTIES

• Application(s): Antiviral agent.
• Application(s): Used especially against herpes.
• Mechanism of Action: Guanosine analog that acts as an antimetabolite.
• Mechanism of Action: Viral (HSV-1, HSV-2 and VZV) thymidine kinase converts aciclovir to the aciclovir monophosphate, which is then converted to the diphosphate by cellular guanylate kinase,
• Mechanism of Action: and finally to the triphosphate by phosphoglycerate kinase, phosphoenolpyruvate carboxykinase, and pyruvate kinase.
• Mechanism of Action: Aciclovir triphosphate competitively inhibits viral DNA polymerase and competes with the natural deoxyguanosine triphosphate, for incorporation into viral DNA.
• Mechanism of Action: Once incorporated, aciclovir triphosphate inhibits DNA synthesis by acting as a chain terminator.

REFERENCES

• Ger. Pat., 1976, 2 539 963; CA, 84, 180300p, (synth)
• Elion, G.B. et al., Proc. Natl. Acad. Sci. U.S.A., 1977, 74, 5716, (pharmacol)
• Fiddian, A.P., Appl. Virol., 1984, 103, (rev, pharmacol)
• Birnbaum, G.I. et al., Can. J. Chem., 1984, 62, 2646, (cryst struct)
• Eur. Pat., 1984, Wellcome, 108 285; CA, 101, 192401e, (Desciclovir, synth, pharmacol)
• Krenitsky, T.A. et al., Proc. Natl. Acad. Sci. U.S.A., 1984, 81, 3209-3213, (synth, pharmacol)
• Krasny, H.C. et al., Biochem. Pharmacol., 1986, 35, 4339, (metab)
• Rees, P.J. et al., J. Antimicrob. Chemother., 1986, 18, 215-222, (pharmacokinet)
• Kelley, J.L. et al., J. Het. Chem., 1986, 23, 271, (synth)
• Chu, C.K. et al., J. Het. Chem., 1986, 23, 289, (rev)
• Radl, S. et al., Cesk. Farm., 1987, 36, 58, (synth)
• Petty, B.G. et al., Antimicrob. Agents Chemother., 1987, 31, 1317-1322, (pharmacokinet)
• Matsumoto, H. et al., Chem. Pharm. Bull., 1988, 36, 1153, (synth)
• Arndt, K.A. et al., J. Am. Acad. Dermatol., 1988, 18, 188, (adverse effects)
• Stimac, A. et al., Synthesis, 1990, 461-464, (synth)
• Reardon, J.E. et al., Adv. Pharmacol., 1991, 22, 1, (rev)
• Alhede, B. et al., J.O.C., 1991, 56, 2139, (synth, cmr)
• De Miranda, P. et al., Antiviral Chem. Chemother., 1992, 3, 1, (metab, rev)
• U.K. Pat., 1993, Norsk Hydro A/S, 2 260 319; CA, 119, 271633g, (acyclovir elaidate)
• Wagstaff, A.J. et al., Drugs, 1994, 47, 153, (rev)
• Buck, I.M. et al., Tetrahedron, 1994, 50, 9195-9206, (synth)
• Jennings, R. et al., Antimicrob. Agents Chemother., 1999, 43, 53-61, (acyclovir elaidate)
• Plass, M. et al., J.C.S. Perkin 2, 1999, 2641-2646, (uv, pmr, ir, Raman)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 602; 628
• Ormrod, D. et al., Drugs, 2000, 59, 839-863; 1317-1359
• Gao, H. et al., Synthesis, 2000, 329-351, (rev)
• Gao, H. et al., Synth. Commun., 2001, 31, 1399-1419, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AEC700; AEC725