Vidarabine

• CAT Number: A000912
• CAS Number: 5536-17-4
• Molecular Formula: C10H13N5O4
• Molecular Weight: 267.2
• Purity: ≥95%
• Synonyms: Adenine arabinoside; Arabinosyladenine; Vira-A; Spongoadenosine; Ara-A
• Target: HSV
• Solubility: >12.4mg/mL in DMSO
• Storage: -20°C
• InChI: 1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1
• InChIKey: OIRDTQYFTABQOQ-UHTZMRCNSA-N
• SMILES: C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)CO)O)O

Vidarabine is an antiviral drug which is active against herpes simplex and varicella zoster viruses. The drug was originally intended as an anti-cancer drug. The anti-viral activity of vidarabine was first described by M. Privat de Garilhe and J. De Rudder in 1964. It was the first nucleoside analog antiviral to be given systemically and was the first agent to be licensed for the treatment of systematic herpes virus infection in humans. It was University of Alabama at Birmingham researcher and physician Dr. Richard Whitley in 1976 where the clinical effectiveness of vidarabine was first realized, and vidarabine was used in the treatment of many viral diseases.

Reference

1: Wang H, Xu T, Yuan J. The use of online heart-cutting high-performance liquid
chromatography coupled with linear ion trap mass spectrometry in the
identification of impurities in vidarabine monophosphate. J Sep Sci. 2017
Apr;40(8):1674-1685. doi: 10.1002/jssc.201601320. Epub 2017 Mar 24. PubMed PMID:
28211639.

2: Nakamura T, Fujita T, Kishimura M, Suita K, Hidaka Y, Cai W, Umemura M,
Yokoyama U, Uechi M, Ishikawa Y. Vidarabine, an Anti-Herpes Virus Agent, Protects
Against the Development of Heart Failure With Relatively Mild Side-Effects on
Cardiac Function in a Canine Model of Pacing-Induced Dilated Cardiomyopathy. Circ
J. 2016 Nov 25;80(12):2496-2505. Epub 2016 Nov 5. PubMed PMID: 27818454.

3: Bravo CA, Vatner DE, Vatner SF. Response to Letter to the Editor on /Does
Vidarabine Mediate Cardioprotection via Inhibition of AC5?/. J Pharmacol Exp
Ther. 2016 Aug;358(2):244-5. doi: 10.1124/jpet.116.234807. PubMed PMID: 27402380.

4: Seifert R. Does Vidarabine Mediate Cardioprotection via Inhibition of AC5? J
Pharmacol Exp Ther. 2016 Aug;358(2):242-3. doi: 10.1124/jpet.116.234245. PubMed
PMID: 27402379.

5: Wada T, Nakamura Y, Cao X, Ohara H, Izumi-Nakaseko H, Ando K, Nakazato Y,
Sugiyama A. Antiviral drug vidarabine possessing cardiac type 5 adenylyl cyclase
inhibitory property did not affect cardiohemodynamic or electrophysiological
variables in the halothane-anesthetized dogs. J Toxicol Sci. 2016
Feb;41(1):115-22. doi: 10.2131/jts.41.115. PubMed PMID: 26763398.

6: Seifert R. Vidarabine is neither a potent nor a selective AC5 inhibitor.
Biochem Pharmacol. 2014 Feb 15;87(4):543-6. doi: 10.1016/j.bcp.2013.12.025. Epub
2014 Jan 4. Review. PubMed PMID: 24398424.

7: Shen W, Kim JS, Mitchell S, Kish P, Kijek P, Hilfinger J. 5/’-O-D-valyl ara A,
a potential prodrug for improving oral bioavailability of the antiviral agent
vidarabine. Nucleosides Nucleotides Nucleic Acids. 2009;28(1):43-55. doi:
10.1080/15257770802581757. PubMed PMID: 19116869; PubMed Central PMCID:
PMC2642978.

8: Shen W, Kim JS, Kish PE, Zhang J, Mitchell S, Gentry BG, Breitenbach JM, Drach
JC, Hilfinger J. Design and synthesis of vidarabine prodrugs as antiviral agents.
Bioorg Med Chem Lett. 2009 Feb 1;19(3):792-6. doi: 10.1016/j.bmcl.2008.12.031.
Epub 2008 Dec 10. PubMed PMID: 19097789; PubMed Central PMCID: PMC2642980.

9: Suzuki M, Okuda T, Shiraki K. Synergistic antiviral activity of acyclovir and
vidarabine against herpes simplex virus types 1 and 2 and varicella-zoster virus.
Antiviral Res. 2006 Nov;72(2):157-61. Epub 2006 May 30. PubMed PMID: 16797734.

10: Miwa N, Kurosaki K, Yoshida Y, Kurokawa M, Saito S, Shiraki K. Comparative
efficacy of acyclovir and vidarabine on the replication of varicella-zoster
virus. Antiviral Res. 2005 Jan;65(1):49-55. PubMed PMID: 15652971.