Adenine, arabinosides

Antiviral Agents. Although a number of antibiotics have been shown to have some sort of antiviral activity, only vidarabine [5536-17-4] (adenine arabinoside) is used clinically against viral infections at this time. As the need for new antiviral agents (qv) increases and new screening procedures are developed, one would expect the discovery of other new effective antiviral antibiotics that could be used safely in human therapy. 

HBV infection remains a major worldwide public health problem. The World Health Organization estimates that there are still 350 million chronic carriers of the vims, who are at risk of developing chronic hepatitis, liver cirrhosis, and hepatocellular carcinoma. The success of IFN-a treatment - mainly performed as combined treatment with adenine-arabinoside - has been measured by the normalization of liver enzymes, loss of HBe antigen and of detectable viral DNA in the serum of patients. It has been estimated from several clinical trials that as many as 40% of treated HBV patients would respond to therapy with IFN-a or combined treatment with nucleoside analogues and IFN-a. 

Utagawa, T., Morisawa, H., Yoshinaga, F., Yamazaki, A., Misugi, K. and Hirose, Y., Microbiological synthesis of adenine arabinoside. Agric. Biol. Chem., 1985, 49, 1053-1058. 

Vidarabine (adenine arabinoside, ara-A) is phos-phorylated in the cell to the triphosphate derivative which blocks DNA synthesis by inhibiting DNA polymerase. It is indicated for infections with herpes simplex virus and varicella-zoster however its use has to a large extend been surpassed by aciclovir. It is administered topically or intravenously. It is inactivated rapidly by adenosine deaminase which for systemic use necessitates constant infusion of the drug. Vidarabine is the least toxic of the purine analogues. Nausea and vomiting are the most frequent adverse effects and neurotoxicity may occur. 

Vidarabine (adenine arabinoside, Vira-A) is an adenine nucleoside analogue containing arabinose in place of ri-bose. It is obtained from cultures of Streptomyces an-tibioticus and has activity against HSV-1, HSV-2, VZV, CMV, HBV, poxviruses, hepadnaviruses, rhabdoviruses, and certain RNA tumor viruses. 

M. T. Cerenzia, L. Fiume, W. D. Venon, B. Lavezzo, M. R. Brunetto, A. Ponzetto, G. Di Stefano, C. Busi, A. Mattioli, G. B. Gervasi, et al., Adenine arabinoside monophosphate coupled to lactosaminated human albumin administered for 4 weeks in patients with chronic type B hepatitis decreased viremia without producing significant side effects, Hepatology 23 657-661 (1996). 

L. Fiume, A. Mattioli, C. Busi, S. Corzani, and G. Di Stefano. High-pressure liquid chromatographic method for determining adenine arabinoside monophosphate coupled to lactosaminated albumin in plasma, Pharm. Acta Helv. 66 230-232 (1991). 

L. Fiume, G. Di Stefano, C. Busi, and A. Mattioli, A conjugate of lactosaminated poly-l-lysine with adenine arabinoside monophosphate, administered to mice by intramuscular route, accomplishes a selective delivery of the drug to the liver. Bio-chem. Pharmacol. 47 643-650 (1994). 

Chemical Name 9-p-D-Arabinofuranosyl-9H-purine-6-amine monohydrate Common Name Adenine arabinoside Spongoadenosine Structural Formula ... 

Vidarabine [vye DARE a been] arabinofuranosyl adenine, ara-A, adenine arabinoside) is one of the most effective of the nucleoside analogs and is also the least toxic. However, it has been supplanted clinically by acyclovir, which is more efficacious and safe. Although vidarabine is active against herpes simplex virus type 1 (HSV-1), HSV-2, and varicella-zoster virus (VZV), its use is limited to treatment of immunocompromised patients with herpes simplex keratitis or encephalitis, or VZV infections. Vidarabine, an adenosine analog, is converted in the cell to its 5 -triphosphate analog (ara-ATP), which is postulated to inhibit viral DNA synthesis. Some resistant herpes virus... 

SYNS ADENINE ARABINOSIDE ARABINOSYLADENINE P-d-ARABINOSYLADENINE 9-ARABINOSYLADENINE VIDARABIN VIDARABINE... 

The use of topical ophthalmic antiviral agents such as idoxuridine and adenine arabinoside generally has been found to be ineffective in the treatment of EKC. However, 1% trifluridine has been shown to decrease replication of adenovirus types 8,13, and 19 in vitro, though no strong evidence exists for its use in EKC patients. 

Cohn J. L adenine-arabinoside en ophtalmologie. [Arabinosyladenine in ophthalmology.] J Fr Ophtalmol 1981 4(6-7) 525-30. 

Vibramycin doxycycline. vidarabine [ban. inn. jan. usan) (adenine arabinoside Ara-A Vira-A ) is a purine nucleoside ANTIVIRAL isolated from the marine gorgonian Evnicella cavoUni and Streptomyces spp. Clinically, it may be used to treat herpes simplex and vaccinia infections. 

Hirota, K Sherker, A. H., Omata, M., Yokosuka, O., and Okuda, K. (1987) Effects of adenine arabinoside on scrum and intraheparic replicative forms of duck hepatitis B virus in chronic infection. Hepatology 7, 24-28. 

Synonyms adenine arabinoside ara-A Trade names Arasena Vira-A Ophthalmic (Pfizer) Indications Herpetic keratoconjunctivitis Category Antiviral, nucleoside analog Half-life 3.3 hours... 

Vidarabine (adenine arabinoside), an analogue of adenosine, does not interfere with purine biosynthesis but affects DNA synthesis. 

It is phosphorylated to adenine arabinoside triphosphate, which inhibits viral DNA polymerases, but not the... 

Adenine arabinoside Nucleoside phosphorylase Enterobacter aerogenes... 

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