General
Preferred name
vidarabine
Synonyms
9-¦Â-D-Arabinofuranosyladenine ()
9-??-D-Arabinofuranosyladenine ()
Adenine arabinoside ()
Ara-A ()
Arabinosyladenine ()
Vira-A ()
9-??D-Arabinofuranosyladenine ()
Vidarabine ()
VIDARABINE ANHYDROUS ()
Vidarabine monohydrate ()
Spongoadenosine monohydrate, Vira-A monohydrate ()
CI-673 ()
NSC-247519 ()
CI 673 ()
Arasena-a ()
NSC-404241 ()
NSC-757383 ()
Vidarabine, anhydrous ()
P&D ID
PD002089
CAS
24356-66-9
5536-17-4
Tags
natural product
drug
available
Approved by
FDA
First approval
1976
Drug Status
investigational
approved
withdrawn
Drug indication
Herpes simplex virus infection
Antiviral
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA
Vidarabine stops replication of herpes viral DNA in 2 ways: 1) competitive inhibition of viral DNA polymerase, and consequently 2) incorporation into and termination of the growing viral DNA chain.; Vidarabine is sequentially phosphorylated by kinases to the triphosphate ara-ATP, which is the active form of vidarabine that acts as both an inhibitor and a substrate of viral DNA polymerase. By acting as a substrate for viral DNA polymerase, ara-ATP competitively inhibits dATP leading to the formation of âfaultyâ DNA. Ara-ATP can also be incorporated into the DNA strand to replace many of the adenosine bases, resulting in the disruption of DNA synthesis.
DESCRIPTION
Vidarabine is an antiviral drug. It is chemically related to .
(GtoPdb)
PHARMACODYNAMICS
Vidarabine is a synthetic purine nucleoside analogue with in vitro and in vivo inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), and varicella-zoster virus (VZV). The inhibitory activity of Vidarabine is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts Vidarabine into Vidarabine monophosphate, a nucleotide analogue. The monophosphate is further converted into diphosphate by cellular guanylate kinase and into triphosphate by a number of cellular enzymes. In vitro, Vidarabine triphosphate stops the DNA replication of herpes virus by being incorporated into the DNA strand and preventing the formation of phosphodiester bridges between bases. This ultimately leads to destabilization of the viral DNA strands.
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
3
Organisms
8
Compound Sets
25
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
NIH Clinical Collections (NCC)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
Withdrawn 2.0
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
74
Molecular Weight
267.1
Hydrogen Bond Acceptors
9
Hydrogen Bond Donors
4
Rotatable Bonds
2
Ring Count
3
Aromatic Ring Count
2
cLogP
-1.98
TPSA
139.54
Fraction CSP3
0.5
Chiral centers
4.0
Largest ring
6.0
QED
0.49
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
DNA Damage/DNA Repair
Tyrosine Kinase/Adaptors
Target
DNA polymerase
Tyrosine Kinases
ADA
DNA/RNA Synthesis
Indication
virus herpes simplex (HSV), varicella-zoster virus (VZV)
MOA
Antiviral
ATC
J05AB03
S01AD06
Therapeutic Class
Antiviral Agents
Source data
