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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13N5O4
Molecular Weight 267.2417
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADENOSINE

SMILES

C([C@]1([H])[C@]([H])([C@]([H])([C@]([H])(n2cnc3c(N)ncnc32)O1)O)O)O

InChI

InChIKey=OIRDTQYFTABQOQ-KQYNXXCUSA-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

625708800000
Curative
VIRA-A

Launch Date

217814400000
Curative
VIRA-A

Launch Date

217814400000
Primary
VIRA-A

Launch Date

217814400000
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Effect of 9-beta-D-arabinofuranosyladenine 5'-monophosphate and 9-beta-D-arabinofuranosylhypoxanthine 5'-monophosphate on experimental herpes simplex keratitis.
1976 Dec
[Preliminary clinical experiences with adenine arabinoside monophosphate (ARA-AMP) in encephalitis due to viruses of the herpes group and varicella/zoster infections (author's transl)].
1979 Nov
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
Comparison of the antiviral effects of 5-methoxymethyldeoxyuridine-5'-monophosphate with adenine arabinoside-5'-monophosphate.
1983 Sep
Inhibitory effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks.
1990 Mar
Liver targeting of nucleoside analogues coupled to galactosyl terminating macromolecules: a new approach to the treatment of a chronic viral hepatitis.
1997 Jun
Regulation of platelet aggregation in vitro by plasma adenosine in preeclampsia.
2001
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
K(ATP)(+) channels, nitric oxide, and adenosine are not required for local metabolic coronary vasodilation.
2001 Feb
Regional differences in mechanisms of cerebral circulatory response to neuronal activation.
2001 Feb
Adenosine-enhanced ischemic preconditioning: adenosine receptor involvement during ischemia and reperfusion.
2001 Feb
Elevated interstitial adenosine concentrations do not activate the muscle reflex.
2001 Feb
New signaling pathways for hormones and cyclic adenosine 3',5'-monophosphate action in endocrine cells.
2001 Feb
Beta,gamma-methylene ATP-induced cAMP formation in C6Bu-1 cells: involvement of local metabolism and subsequent stimulation of adenosine A2B receptor.
2001 Feb
Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection.
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
Adenosine triphosphate-evoked cytosolic calcium oscillations in human granulosa-luteal cells: role of protein kinase C.
2001 Feb
Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes.
2001 Feb
Dysregulation of extracellular adenosine levels by vascular smooth muscle cells from spontaneously hypertensive rats.
2001 Feb
Adenosine as a neuromodulator and as a homeostatic regulator in the nervous system: different roles, different sources and different receptors.
2001 Feb
Distinct modulation of evoked and spontaneous EPSCs by purinoceptors in the nucleus tractus solitarii of the rat.
2001 Feb 1
Full hematopoietic engraftment after allogeneic bone marrow transplantation without cytoreduction in a child with severe combined immunodeficiency.
2001 Feb 1
Melphalan and purine analog-containing preparative regimens: reduced-intensity conditioning for patients with hematologic malignancies undergoing allogeneic progenitor cell transplantation.
2001 Feb 1
Adenosine-mediated presynaptic modulation of glutamatergic transmission in the laterodorsal tegmentum.
2001 Feb 1
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
Potentiation of cytokine induction of group IIA phospholipase A(2) in rat mesangial cells by ATP and adenosine via the A2A adenosine receptor.
2001 Jan
Quantitative relationship between the chemical structure of antisense nucleosides and their capacity to interact with cyclomalto-octaose.
2001 Jan
Myocardial perfusion in patients with permanent ventricular pacing and normal coronary arteries.
2001 Jan
Hoechst 33342-induced apoptosis is associated with intracellular accumulation of E2F-1 protein in BC3H-1 myocytes and HL-60 cells.
2001 Jan
Extracellular ATP formation on vascular endothelial cells is mediated by ecto-nucleotide kinase activities via phosphotransfer reactions.
2001 Jan
Purines inhibit poly(ADP-ribose) polymerase activation and modulate oxidant-induced cell death.
2001 Jan
Differential effect of adenosine on tumor and normal cell growth: focus on the A3 adenosine receptor.
2001 Jan
Paroxysmal supraventricular tachycardia: outcome after ED care.
2001 Jan
A novel transverse push-pull microprobe: in vitro characterization and in vivo demonstration of the enzymatic production of adenosine in the spinal cord dorsal horn.
2001 Jan
Cellular distribution of constitutively active mutant parathyroid hormone (PTH)/PTH-related protein receptors and regulation of cyclic adenosine 3',5'-monophosphate signaling by beta-arrestin2.
2001 Jan
Effects of neuroprotective cocktails on hippocampal neuron death in an in vitro model of cerebral ischemia.
2001 Jan
Pharmacokinetic-pharmacodynamic modeling of the antilipolytic effects of an adenosine receptor agonist in healthy volunteers.
2001 Jan
Influence of adduct position and sequence length on the ligation of oligonucleotides containing benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts into M13mp7L2.
2001 Jan
P2 receptor agonists stimulate insulin release from human pancreatic islets.
2001 Jan
Motivational effects of ethanol in DARPP-32 knock-out mice.
2001 Jan 1
Nucleotide-dependent single- to double-headed binding of kinesin.
2001 Jan 26
Estrogen modulates norepinephrine-induced accumulation of adenosine cyclic monophosphate in a subpopulation of immortalized luteinizing hormone-releasing hormone secreting neurons from the mouse hypothalamus.
2001 Jan 26
Nucleoside transport inhibition in ischemic myocardium results in enhanced taurine efflux.
2001 Jan 5
Differential patterns of sympathetic responses to selective stimulation of nucleus tractus solitarius purinergic receptor subtypes.
2001 Jan-Feb
Patents

Sample Use Guides

Adult Patients:
Route of Administration: Intravenous
Name Type Language
ADENOSINE
EP   HSDB   INCI   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INCI   USAN  
Official Name English
ADENOSINE [EP MONOGRAPH]
Common Name English
9-.BETA.-D-RIBOFURANOSYLADENINE
Common Name English
ADENOSINE [VANDF]
Common Name English
ADENOSINE [ORANGE BOOK]
Common Name English
ADENOSINE [MART.]
Common Name English
ADENOSCAN
Brand Name English
ADENOSINE [MI]
Common Name English
NSC-7652
Code English
SR 96225
Code English
ADENOSINE [JAN]
Common Name English
ADENOCARD
Brand Name English
ADENOSINE [USP MONOGRAPH]
Common Name English
ADENOSINE [USP-RS]
Common Name English
6-AMINO-9-.BETA.-D-RIBOFURANOSYL-9H-PURINE
Common Name English
ADENOSINE [EP]
Common Name English
ADENOSINE [HSDB]
Common Name English
ADENOSINE [INCI]
Common Name English
SR-96225
Code English
ADENOSINE [USAN]
Common Name English
Classification Tree Code System Code
DSLD 496 (Number of products:57)
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
LOINC 75136-2
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
WHO-ATC C01EB10
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
FDA ORPHAN DRUG 32388
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
NCI_THESAURUS C707
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
LOINC 75142-0
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
WHO-VATC QC01EB10
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
NDF-RT N0000178375
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
NDF-RT N0000175788
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
LOINC 75160-2
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
Code System Code Type Description
EPA CompTox
58-61-7
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
RXCUI
296
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00640
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
MESH
D000241
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
EVMPD
SUB00297MIG
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
WIKIPEDIA
ADENOSINE
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
IUPHAR
2844
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
USP_CATALOG
1012123
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY USP-RS
FDA UNII
K72T3FS567
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
MERCK INDEX
M1411
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY Merck Index
HSDB
7774
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
PUBCHEM
60961
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL477
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
DRUG CENTRAL
90
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-389-9
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
NCI_THESAURUS
C207
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY
CAS
58-61-7
Created by admin on Fri Jun 25 20:56:24 UTC 2021 , Edited by admin on Fri Jun 25 20:56:24 UTC 2021
PRIMARY