U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13N5O4
Molecular Weight 267.2413
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VIDARABINE ANHYDROUS

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O

InChI

InChIKey=OIRDTQYFTABQOQ-UHTZMRCNSA-N
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

HIDE SMILES / InChI
Vidarabine or 9-β-D-arabinofuranosyladenine (ara-A, trade name Vira-A) is a synthetic purine nucleoside analog 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 analog. 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 replication of herpes viral DNA. When used as a substrate for viral DNA polymerase, Vidarabine triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where Vidarabine triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ADENOCARD

Approved Use

Intravenous Adenocard (adenosine injection) is indicated for the following. Conversion to sinus rhythm of paroxysmal supraventricular tachycardia (PSVT), including that associated with accessory bypass tracts (Wolff-Parkinson-White Syndrome). When clinically advisable, appropriate vagal maneuvers (e.g., Valsalva maneuver), should be attempted prior to Adenocard administration.

Launch Date

6.2570883E11
Curative
VIRA-A

Approved Use

Unknown

Launch Date

2.17814401E11
Curative
VIRA-A

Approved Use

Unknown

Launch Date

2.17814401E11
Primary
VIRA-A

Approved Use

Unknown

Launch Date

2.17814401E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
7.5 mg/kg 1 times / day multiple, intravenous
dose: 7.5 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
HYPOXANTHINE ARABINOSIDE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Anti-herpesvirus activity of adenine arabinoside analogues in tissue culture and a genital infection of mice and guinea pigs.
1982 May
Effect of combinations of acyclovir with vidarabine or its 5'-monophosphate on herpes simplex viruses in cell culture and in mice.
1982 Sep
Lipolysis is an important determinant of isoproterenol-induced myocardial necrosis.
1999 Sep-Oct
Adenine-induced selective apoptosis toward HIV chronically infected cells in vitro.
2000 Jul 14
Metabolic fate of extracellular NAD in human skin fibroblasts.
2001
Effects of postsynaptic GABA(B) receptor activation on epileptiform activity in hippocampal slices.
2001
Adenosine A(1) and A(3) receptors mediate inhibition of synaptic transmission in rat cortical neurons.
2001
Autoimmune thrombocytopenia associated with the first cycle of fludarabine therapy in the treatment of relapsed non-Hodgkin's lymphoma.
2001
Treatment of aggressive, or progressing indolent peripheral T- and NK-cell neoplasias by combination of fludarabine, cyclophosphamide and doxorubicine.
2001 Apr
Dose-reduced conditioning and allogeneic hematopoietic stem cell transplantation from unrelated donors in 42 patients.
2001 Aug
Impact of therapy With chlorambucil, fludarabine, or fludarabine plus chlorambucil on infections in patients with chronic lymphocytic leukemia: Intergroup Study Cancer and Leukemia Group B 9011.
2001 Aug 15
Glucocorticoids protect against apoptosis induced by serum deprivation, cyclic adenosine 3',5'-monophosphate and p53 activation in immortalized human granulosa cells: involvement of Bcl-2.
2001 Feb
The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus.
2001 Feb
Mechanism of prolonged vasorelaxation to ATP in the rat isolated mesenteric arterial bed.
2001 Feb
Elevated interstitial adenosine concentrations do not activate the muscle reflex.
2001 Feb
Construction of gene therapy vectors targeting thyroid cells: enhancement of activity and specificity with histone deacetylase inhibitors and agents modulating the cyclic adenosine 3',5'-monophosphate pathway and demonstration of activity in follicular and anaplastic thyroid carcinoma cells.
2001 Feb
Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes.
2001 Feb
Molecular remission following high-dose hydroxyurea and fludarabine plus cytarabine in a patient with simultaneous acute myeloid leukemia and low-grade lymphoma.
2001 Feb
Second primary tumors and immune phenomena after fludarabine or 2-chloro-2'-deoxyadenosine treatment.
2001 Feb
Deoxynucleoside kinases encoded by the yaaG and yaaF genes of Bacillus subtilis. Substrate specificity and kinetic analysis of deoxyguanosine kinase with UTP as the preferred phosphate donor.
2001 Feb 23
The main products of the low molecular mass fraction in the venom of the spider Latrodectus menavodi.
2001 Feb-Mar
Effects of extracellular nucleotides and nucleosides on prostate carcinoma cells.
2001 Jan
The critical role of adenosine and guanosine in the affinity of dinucleoside polyphosphates to P(2X)-receptors in the isolated perfused rat kidney.
2001 Jan
Two subtypes of G protein-coupled nucleotide receptors, P2Y(1) and P2Y(2) are involved in calcium signalling in glioma C6 cells.
2001 Jan
Activity of adenosine diphosphates and triphosphates on a P2Y(T) -type receptor in brain capillary endothelial cells.
2001 Jan
Quantitative assessment of myocardial perfusion during graded coronary stenosis by real-time myocardial contrast echo refilling curves.
2001 Jan
Purines inhibit poly(ADP-ribose) polymerase activation and modulate oxidant-induced cell death.
2001 Jan
Efferent arteriole tubuloglomerular feedback in the renal nephron.
2001 Jan
Adenosine A2B receptors behave as an alternative anchoring protein for cell surface adenosine deaminase in lymphocytes and cultured cells.
2001 Jan
S-Adenosyl-L-homocysteine hydrolase inhibitor mediates immunosuppressive effects in vivo: suppression of delayed type hypersensitivity ear swelling and peptidoglycan polysaccharide-induced arthritis.
2001 Jan
Short-term hibernation in adult cardiomyocytes is PO(2) dependent and Ca(2+) mediated.
2001 Jan
Preconditioning of the distal portion of a rat random-pattern skin flap.
2001 Jan
Interleukin-6 enhances expression of adenosine A(1) receptor mRNA and signaling in cultured rat cortical astrocytes and brain slices.
2001 Jan
Activation of extracellular signal-regulated kinases, NF-kappa B, and cyclic adenosine 5'-monophosphate response element-binding protein in lung neutrophils occurs by differing mechanisms after hemorrhage or endotoxemia.
2001 Jan 1
Vasoactive intestinal peptide-stimulated adenosine 3',5'-cyclic monophosphate formation in cerebral cortex and hypothalamus of chick and rat: comparison of the chicken and mammalian peptide.
2001 Jan 12
Repeated administration of CGP 46381, a gamma-aminobutyric acidB antagonist, and ethosuximide suppresses seizure-associated cyclic adenosine 3'5' monophosphate response element- and activator protein-1 DNA-binding activities in lethargic (lh/lh) mice.
2001 Jan 19
Nucleotide-dependent single- to double-headed binding of kinesin.
2001 Jan 26
Nucleoside transport inhibition in ischemic myocardium results in enhanced taurine efflux.
2001 Jan 5
Failure of sustained engraftment after non-myeloablative conditioning with low-dose TBI and T cell-reduced allogeneic peripheral stem cell transplantation.
2001 Jul
Flavopiridol circumvents Bcl-2 family mediated inhibition of apoptosis and drug resistance in B-cell chronic lymphocytic leukaemia.
2001 Jul
Imbalanced DNA synthesis induced by cytosine arabinoside and fludarabine in human leukemia cells.
2001 Jul 1
Will mixed chimerism cure autoimmune diseases after a nonmyeloablative stem cell transplant?
2001 Jul 27
Nucleoside analogues in the treatment of haematological malignancies.
2001 Jun
Efficacy of fludarabine, intermittent sequential high-dose cytosine arabinoside, and mitoxantrone (FIS-HAM) salvage therapy in highly resistant acute leukemias.
2001 Jun
Nonmyeloablative hematopoietic cell transplantation. Replacing high-dose cytotoxic therapy by the graft-versus-tumor effect.
2001 Jun
ADP is the cognate ligand for the orphan G protein-coupled receptor SP1999.
2001 Mar 16
Cytosolic high K(m) 5'-nucleotidase and 5'(3')-deoxyribonucleotidase in substrate cycles involved in nucleotide metabolism.
2001 Mar 2
Equilibrium binding of single-stranded DNA to the secondary DNA binding site of the bacterial recombinase RecA.
2001 Mar 30
Phosphodiesterase type 4 inhibitor suppresses expression of anti-apoptotic members of the Bcl-2 family in B-CLL cells and induces caspase-dependent apoptosis.
2001 Oct
Cyclosporin A for the treatment of cytopenia associated with chronic lymphocytic leukemia.
2001 Oct 15
Patents

Sample Use Guides

Adult Patients: Initial dose: 6 mg given as a rapid intravenous bolus (administered over a 1-2 second period). Repeat administration: If the first dose does not result in elimination of the supraventricular tachycardia within 1-2 minutes, 12 mg should be given as a rapid intravenous bolus. This 12 mg dose may be repeated a second time if required. Pediatric Patients: Initial dose: Give 0.05 to 0.1 mg/kg as a rapid IV bolus given either centrally or peripherally. A saline flush should follow. Repeat administration: If conversion of PSVT does not occur within 1-2 minutes, additional bolus injections of adenosine can be administered at incrementally higher doses, increasing the amount given by 0.05 to 0.1 mg/kg. Follow each bolus with a saline flush. This process should continue until sinus rhythm is established or a maximum single dose of 0.3 mg/kg is used. Pediatric Patients with a Body Weight ≥ 50 kg: Administer the adult dose.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Name Type Language
VIDARABINE ANHYDROUS
Common Name English
NSC-404241
Code English
NSC-247519
Code English
ARASENA-A
Brand Name English
VIDARABINE [HSDB]
Common Name English
9-.BETA.-D-ARABINOFURANOSYL-9H-PURIN-6-AMINE
Common Name English
VIDARABINE [MI]
Common Name English
VIDARABINE, ANHYDROUS
Common Name English
vidarabine [INN]
Common Name English
9H-PURIN-6-AMINE, 9-.BETA.-D-ARABINOFURANOSYL-
Common Name English
CI-673
Code English
VIRA-A
Brand Name English
Vidarabine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AB03
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
NCI_THESAURUS C29575
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
NCI_THESAURUS C1556
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
WHO-ATC S01AD06
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
NCI_THESAURUS C281
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
Code System Code Type Description
NSC
247519
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
ECHA (EC/EINECS)
226-893-9
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
FDA UNII
3XQD2MEW34
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
NCI_THESAURUS
C77393
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
MERCK INDEX
M11443
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY Merck Index
CAS
5536-17-4
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
RXCUI
2108659
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
PUBCHEM
21704
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID80873976
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
DAILYMED
3XQD2MEW34
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
EVMPD
SUB00047MIG
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
INN
2842
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
NSC
404241
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
HSDB
6514
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY