Vidarabine

Vidarabine
Clinical data

AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	J05AB03 (WHO) S01AD06 (WHO)
Pharmacokinetic data
Protein binding	24-38%
Identifiers
IUPAC name (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol hydrate
CAS Number	24356-66-9^Y
PubChem (CID)	21704
IUPHAR/BPS	4806
DrugBank	DB00194^Y
ChemSpider	20400^N
UNII	FA2DM6879K^Y
KEGG	D00406^Y
ChEMBL	CHEMBL1090^N
NIAID ChemDB	007328
ECHA InfoCard	100.203.402
Chemical and physical data
Formula	C₁₀H₁₅N₅O₅
Molar mass	285.257 g/mol
3D model (Jmol)	Interactive image
SMILES C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N
InChI 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^N Key:OIRDTQYFTABQOQ-UHTZMRCNSA-N^N
^NY (what is this?)

Vidarabine or 9-β-D-arabinofuranosyladenine (ara-A) is an antiviral drug which is active against herpes simplex and varicella zoster viruses.

In the 1950s two nucleosides were isolated from the Caribbean sponge Tethya crypta: spongothymidine and spongouridine; which contained D-arabinose rather than D-ribose. These compounds led to the synthesis of a new generation, sugar modified nucleoside analog vidarabine, and the related compound cytarabine. In 2004 these were the only marine related compounds in clinical use.

The drug was first synthesized in 1960 in the Bernard Randall Baker lab at the Stanford Research Institute (now SRI International).

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 Richard J. Whitley in 1976 where the clinical effectiveness of vidarabine was first realized, and vidarabine was used in the treatment of many viral diseases.

Vidarabine is an analog of adenosine with the D-ribose, replaced with D-arabinose. As you can see from figure 1.1 that it is a stereoisomer of adenosine. It has a half-life of 60 minutes, and its solubility is 0.05%, and is able to cross the blood–brain barrier (BBB) when converted to its active metabolite.

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Wikipedia