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 ADENOSINE

SMILES

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

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

Molecular Formula C10H13N5O4
Molecular Weight 267.2413
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Regulation of platelet aggregation in vitro by plasma adenosine in preeclampsia.
2001
RNA fragmentation studied in a matrix-assisted laser desorption/ionisation tandem quadrupole/orthogonal time-of-flight mass spectrometer.
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
Regulation of G protein-coupled receptor-adenylyl cyclase responsiveness in human airway smooth muscle by exogenous and autocrine adenosine.
2001 Feb
K(ATP)(+) channels, nitric oxide, and adenosine are not required for local metabolic coronary vasodilation.
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
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
Adenosine as a neuromodulator and as a homeostatic regulator in the nervous system: different roles, different sources and different receptors.
2001 Feb
Adenosine-mediated presynaptic modulation of glutamatergic transmission in the laterodorsal tegmentum.
2001 Feb 1
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
Nitrogen-dependent accumulation of cytokinins in root and the translocation to leaf: implication of cytokinin species that induces gene expression of maize response regulator.
2001 Jan
Quantitative relationship between the chemical structure of antisense nucleosides and their capacity to interact with cyclomalto-octaose.
2001 Jan
Sildenafil citrate (Viagra) does not exacerbate myocardial ischemia in canine models of coronary artery stenosis.
2001 Jan
Quantitative assessment of myocardial perfusion during graded coronary stenosis by real-time myocardial contrast echo refilling curves.
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
Perioperative activation of hemostasis in vascular surgery patients.
2001 Jan
Efferent arteriole tubuloglomerular feedback in the renal nephron.
2001 Jan
Extracellular adenosine modulates a volume-sensitive-like chloride conductance in immortalized rabbit DC1 cells.
2001 Jan
Adenosine A1 receptor activation reduces reactive oxygen species and attenuates stunning in ventricular myocytes.
2001 Jan
Adenosine attenuates reperfusion-induced apoptotic cell death by modulating expression of Bcl-2 and Bax proteins.
2001 Jan
Adenosine A2B receptors behave as an alternative anchoring protein for cell surface adenosine deaminase in lymphocytes and cultured cells.
2001 Jan
A3 adenosine receptor activation triggers phosphorylation of protein kinase B and protects rat basophilic leukemia 2H3 mast cells from apoptosis.
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
Motivational effects of ethanol in DARPP-32 knock-out mice.
2001 Jan 1
Cyclic GMP-dependent relaxation of isolated rat renal glomeruli induced by extracellular ATP.
2001 Jan 1
Immunohistochemical localization of adenosine A1 receptors in human brain regions.
2001 Jan 19
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
Exercise training in coronary artery disease and coronary vasomotion.
2001 Jan 2
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
Structure-activity studies of 5-substituted pyridopyrimidines as adenosine kinase inhibitors.
2001 Jan 8
Differential patterns of sympathetic responses to selective stimulation of nucleus tractus solitarius purinergic receptor subtypes.
2001 Jan-Feb
Expression, but not activity, of neuronal nitric oxide synthase is regionally increased in the alcoholic brain.
2001 Jan-Feb
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
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:48:41 UTC 2023
Edited
by admin
on Wed Jul 05 22:48:41 UTC 2023
Record UNII
K72T3FS567
Record Status Validated (UNII)
Record Version
  • Download
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 [EP IMPURITY]
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 [HSDB]
Common Name English
ADENOSINE [INCI]
Common Name English
SR-96225
Code English
ADENOSINE [USAN]
Common Name English
Adenosine [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 496 (Number of products:57)
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
LOINC 75136-2
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
WHO-ATC C01EB10
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
FDA ORPHAN DRUG 32388
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
NCI_THESAURUS C707
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
LOINC 75142-0
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
WHO-VATC QC01EB10
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
NDF-RT N0000178375
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
NDF-RT N0000175788
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
LOINC 75160-2
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID1022558
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
RXCUI
296
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB00640
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
CHEBI
16335
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
MESH
D000241
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
EVMPD
SUB00297MIG
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
WIKIPEDIA
ADENOSINE
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
DAILYMED
K72T3FS567
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
IUPHAR
2844
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
SMS_ID
100000078834
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
FDA UNII
K72T3FS567
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
MERCK INDEX
M1411
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY Merck Index
HSDB
7774
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
PUBCHEM
60961
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
ChEMBL
CHEMBL477
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
DRUG CENTRAL
90
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-389-9
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
RS_ITEM_NUM
1012123
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
NCI_THESAURUS
C207
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
NSC
7652
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
CAS
58-61-7
Created by admin on Wed Jul 05 22:48:41 UTC 2023 , Edited by admin on Wed Jul 05 22:48:41 UTC 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
TARGET -> AGONIST
Ki
INHIBITOR OF EXPRESSION->TARGET
Reduces the production of adenosine
Related Record Type Details
METABOLITE -> PARENT
Adenosine is broken down by adenosine deaminase, which is present in red cells and the vessel wall.
MAJOR
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity A = 0.6; impurity G = 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity A = 0.6; impurity G = 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY