◎ Sugi Atlas

Atlas / Drug / Adenosine

Adenosine

drug
On this page

Also known as AdenocardAdenocorAdenoscanNSC-7652SR 96225SR-96225SID26751564SID50104175SID855932SID90341699SID144204442SID170465447AdenosineÊAdenosineÂVIDARABINE_ADENOSINE

Summary

Adenosine (CHEMBL477) is an approved small-molecule anti-arrhythmia drug (ATC C01EB10) targeting ADORA1, ADORA2A, and ADORA2B; indicated across 22 conditions including cardiovascular disorder and wolff-parkinson-white syndrome.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: C01EB10
  • Targets: 7 (ADORA1, ADORA2A, ADORA2B…)
  • Indications: 22 conditions
  • Clinical trials: 68
  • Chemistry: 267.24 Da · C10H13N5O4

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL477
NameAdenosine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID60961
ChEBICHEBI:16335
ATCC01EB10
Molecular formulaC10H13N5O4
Molecular weight267.24
InChIKeyOIRDTQYFTABQOQ-KQYNXXCUSA-N

SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N

IUPAC name: (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

ChEBI definition: A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a β‒N9-glycosidic bond.

Pharmacological roles (ChEBI): anti-arrhythmia drug, vasodilator agent, analgesic.

Other ChEBI roles (chemical / environmental): human metabolite, fundamental metabolite.

Also known as: Adenocard, Adenocor, Adenoscan, Adenosine, NSC-7652, SR 96225, SR-96225, adenosine, SID26751564, SID50104175, SID855932, ADENOSINE

Patent coverage: 70,815 distinct patent families (222,014 SureChEMBL compound mentions), from 4 matched compound structure(s). One matched structure accounts for 221,969 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
ADORA1A1 receptorAgonist70.3%P30542
ADORA2AA2A receptorAgonist6.510.4%P29274
ADORA2BA2B receptorAgonist4.820.5%P29275
ADORA3A3 receptorAgonist6.540%P0DMS8
PI4K2Aphosphatidylinositol 4-kinase type 2 alphaInhibition50.6%Q9BTU6
PI4K2Bphosphatidylinositol 4-kinase type 2 betaInhibition50.1%Q8TCG2
TRPM4TRPM43.20.5%Q8TD43

Broader ChEMBL bioactivity targets: 25 (assay-derived). Sample: Nuclear receptor ROR-gamma, Survival motor neuron protein, Histone-lysine N-methyltransferase, H3 lysine-79 specific, Equilibrative nucleoside transporter 1, Menin/Histone-lysine N-methyltransferase MLL, Adenosine A2 receptor, Adenosine A2 receptor, Phosphatidylinositol 4-kinase, PI4K, cAMP-dependent protein kinase A, Adenosine receptor A1.

Bioactivity

ChEMBL activities: 60 potent at pChembl ≥ 5 of 80 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
ADORA38.94IC501.15nMCHEMBL_ACT_16486677
ADORA18.63IC502.34nMCHEMBL_ACT_16486666
P292768.3Ki5nMCHEMBL_ACT_1197734
P250998.29Ki5.1nMCHEMBL_ACT_137331
P250998Ki10nMCHEMBL_ACT_1197733
P250998Ki10nMCHEMBL_ACT_708360
P250997.89Ki12.8nMCHEMBL_ACT_71801
P250997.89Ki12.8nMCHEMBL_ACT_952061
ADORA37.87EC5013.49nMCHEMBL_ACT_24669299
ADORA2A7.76Kd17.3nMCHEMBL_ACT_24781552
ADORA2A7.7Ki20nMCHEMBL_ACT_8031116
ADORA2A7.6EC5025.12nMCHEMBL_ACT_24669211
P305437.52Ki30nMCHEMBL_ACT_708361
P292767.43Ki37nMCHEMBL_ACT_71802
P292767.43Ki37nMCHEMBL_ACT_952062
ADORA17.41EC5039nMCHEMBL_ACT_12089151
ADORA2A7.29EC5051.29nMCHEMBL_ACT_1160886
ADORA2A7.29EC5051.29nMCHEMBL_ACT_785271
ADORA2B7.28EC5052.48nMCHEMBL_ACT_24669255
ADORA17.16EC5069.18nMCHEMBL_ACT_24669122
P286477Ki100nMCHEMBL_ACT_708363
ADORA2A6.82Ki150nMCHEMBL_ACT_24781579
ADORA36.54EC50290nMCHEMBL_ACT_14644313
ADORA36.54EC50290nMCHEMBL_ACT_16493407
ADORA36.54Ki290nMCHEMBL_ACT_24781677
ADORA36.54EC50290nMCHEMBL_ACT_3352045
ADORA36.54EC50290nMCHEMBL_ACT_6161629
ADORA16.53Kd295.1nMCHEMBL_ACT_24669427
ADORA16.51EC50310nMCHEMBL_ACT_14644298
ADORA16.51EC50310nMCHEMBL_ACT_16493404

Target pathways

Aggregated over 7 target gene(s): ADORA1, ADORA2A, ADORA2B, ADORA3, PI4K2A, PI4K2B, TRPM4.

Top Reactome pathways

29 total, by targets touching each:

PathwayTargetsGenes
Signal Transduction4ADORA1, ADORA2A, ADORA2B, ADORA3
Signaling by GPCR4ADORA1, ADORA2A, ADORA2B, ADORA3
Class A/1 (Rhodopsin-like receptors)4ADORA1, ADORA2A, ADORA2B, ADORA3
GPCR downstream signalling4ADORA1, ADORA2A, ADORA2B, ADORA3
Adenosine P1 receptors4ADORA1, ADORA2A, ADORA2B, ADORA3
Nucleotide-like (purinergic) receptors4ADORA1, ADORA2A, ADORA2B, ADORA3
GPCR ligand binding4ADORA1, ADORA2A, ADORA2B, ADORA3
Synthesis of PIPs at the plasma membrane2PI4K2A, PI4K2B
Synthesis of PIPs at the Golgi membrane2PI4K2A, PI4K2B
Synthesis of PIPs at the early endosome membrane2PI4K2A, PI4K2B
Metabolism of proteins2ADORA2A, ADORA2B
G alpha (s) signalling events2ADORA2A, ADORA2B
G alpha (i) signalling events2ADORA1, ADORA3
Surfactant metabolism2ADORA2A, ADORA2B
Synthesis of PIPs at the ER membrane1PI4K2B
Disease1ADORA2B
Signaling by NTRKs1ADORA2A
Activation of TRKA receptors1ADORA2A
NGF-independant TRKA activation1ADORA2A
Signaling by NTRK1 (TRKA)1ADORA2A
TRP channels1TRPM4
Infectious disease1ADORA2B
Signaling by Receptor Tyrosine Kinases1ADORA2A
Leishmania infection1ADORA2B
ADORA2B mediated anti-inflammatory cytokines production1ADORA2B
Anti-inflammatory response favouring Leishmania parasite infection1ADORA2B
Leishmania parasite growth and survival1ADORA2B
Sensory perception of sweet, bitter, and umami (glutamate) taste1TRPM4
Parasitic Infection Pathways1ADORA2B

Dominant GO biological processes

GO termTargets
signal transduction4
G protein-coupled receptor signaling pathway4
G protein-coupled adenosine receptor signaling pathway4
inflammatory response3
negative regulation of cell population proliferation3
vasodilation3
presynaptic modulation of chemical synaptic transmission3
phagocytosis2
cell-cell signaling2
response to purine-containing compound2
excitatory postsynaptic potential2
apoptotic signaling pathway2
negative regulation of inflammatory response2
adenylate cyclase-activating G protein-coupled receptor signaling pathway2
regulation of norepinephrine secretion2

Indications & clinical

Indications

22 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
cardiovascular disorder4MONDO:0004995EFO:0000319
Wolff-Parkinson-White syndrome4MONDO:0008685EFO:1001450
neoplasm3MONDO:0005070EFO:0000616
myocardial infarction3MONDO:0005068EFO:0000612
atrial fibrillation3MONDO:0004981EFO:0000275
ventricular tachycardia3MONDO:0005477EFO:0005306
acute myocardial infarction3MONDO:0004781EFO:0008583
myocardial ischemia3MONDO:0024644EFO:1001375
coronary stenosis3MONDO:0006715MONDO:0006715
cardiomyopathy2MONDO:0004994EFO:0000318
coronary artery disorder2MONDO:0005010EFO:0001645
Tako-tsubo cardiomyopathy2MONDO:0019018EFO:1002000
ST-elevation myocardial infarction2MONDO:0041656EFO:0008585
acute respiratory distress syndrome2MONDO:0006502EFO:1000637
B-cell chronic lymphocytic leukemia1MONDO:0004948EFO:0000095
ischemic disease1MONDO:0005053EFO:0000556
leukemia1MONDO:0005059EFO:0000565

5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 68.

Phase distribution

PhaseTrials
Not specified20
PHASE314
PHASE411
PHASE29
PHASE16
PHASE1/PHASE23
EARLY_PHASE13
PHASE2/PHASE32

Top trials by phase / activity

NCTPhaseStatusTitle
NCT03218137PHASE4RECRUITINGUse of Adenosine to Determine the Electrophysiological Mechanism of Premature Ventricular Contractions
NCT04666454PHASE4RECRUITINGBROKEN-SWEDEHEART- Optimized Pharmacological Treatment for Broken Heart (Takotsubo) Syndrome.
NCT06578234PHASE4RECRUITINGHyperemic mYocardial Perfusion by adEnosine at diffeRent Doses
NCT06993038PHASE4RECRUITINGAdenosine vs Diltiazem for Treatment of SVT in the ED
NCT07536802PHASE4RECRUITINGAdenosine Pre-Medication in Primary Percutaneous Coronary Intervention
NCT00413712PHASE4COMPLETEDEffectiveness of Calcium Channel Blockers and Adenosine in the Emergency Management of SVT
NCT03249272PHASE4TERMINATEDMicrovascular Dysfunction in Nonischemic Cardiomyopathy: Insights From CMR Assessment of Coronary Flow Reserve
NCT03557385PHASE4COMPLETEDAdenosine Contrast CorrELations in Evaluating RevAscularizaTION
NCT04699110PHASE4COMPLETEDAdrenaline for the Treatment of No-Reflow in Normotensive Patients
NCT07456423PHASE4COMPLETEDAdenosine vs. Diltiazem
NCT07554170PHASE4COMPLETEDComparison of Single-syringe vs. Double-syringe Techniques for Adenosine Administration in PSVT
NCT06717685PHASE3RECRUITINGEfficacy of Adenosine as Compared to Verapamil in Paroxysmal Supraventricular Tachycardia (pSVT) Patients
NCT00208299PHASE3COMPLETEDADVANCE MPI 1: Study of Regadenoson Versus Adenoscan® in Patients Undergoing Myocardial Perfusion Imaging (MPI)
NCT00208312PHASE3COMPLETEDADVANCE MPI 2: Study of Regadenoson Versus Adenoscan® in Patients Undergoing Myocardial Perfusion Imaging (MPI)
NCT00590070PHASE2/PHASE3COMPLETEDTHE REOPEN-AMI STUDY - Intracoronary Nitroprusside Versus Adenosine in Acute Myocardial Infarction
NCT00612521PHASE3TERMINATEDProphylactic Intra-coronary Adenosine to Prevent Post Coronary Artery Stenting Myonecrosis
NCT00781404PHASE3COMPLETEDMyocardial Protection With Adenosine During Primary Percutaneous Coronary Intervention in Pts With STEMI
NCT00944294PHASE3COMPLETEDEfficacy and Safety Study of Binodenoson in Assessing Cardiac Ischemia
NCT00944970PHASE3COMPLETEDEfficacy and Safety Study of Binodenoson in Assessing Cardiac Ischemia
NCT00990327PHASE3TERMINATEDStudy of the Safety and Efficacy of Apadenoson for Detection of Myocardial Perfusion Defects Using SPECT MPI
NCT01148147PHASE3COMPLETEDIntracoronary Adenosine Administration to Prevent Periprocedural Myonecrosis in Elective Coronary Angioplasty
NCT01234870PHASE2/PHASE3COMPLETEDComprehensive Evaluation of Ischemic Heart Disease Using MRI
NCT01313572PHASE3TERMINATEDStudy of the Safety and Efficacy of Apadenoson for Detection of Myocardial Perfusion Defects Using SPECT MPI
NCT01809743PHASE3COMPLETEDRegadenoson and Adenosine
NCT03231371PHASE3COMPLETEDCoronary Artery Vasculopathy in Pediatric Heart Transplant Patients
NCT04392362PHASE3COMPLETEDA Trial to Compare American Heart Association (AHA) and Simple (SIM)Method to Give Adenosine to Treat Supra-ventricular Tachycardia (SVT)
NCT05014061PHASE3WITHDRAWNAdenosine’s Effect on STunning Resolution in Acute Myocardial Infarction
NCT00284323PHASE2UNKNOWNSalvage: Postconditioning With Adenosine for STEMI
NCT00298636PHASE2COMPLETEDDose-Response of Adenosine for Perioperative Pain
NCT00349921PHASE2COMPLETEDClonidine Versus Adenosine to Treat Neuropathic Pain
NCT00845689PHASE1/PHASE2UNKNOWNPrevention of Liver Damage During Liver Surgery
NCT00881686PHASE1/PHASE2COMPLETEDMyocardial Protection With Adenosine Preconditioning
NCT01123525PHASE1/PHASE2COMPLETEDAdenosine Cardioplegia; Improved Cardioprotection?
NCT01593644PHASE2UNKNOWNPhase II Study for the Diagnosis and Functional Assessment of CAD Using Transthoracic-Echodoppler
NCT02681913PHASE2UNKNOWNAdenosine as an Adjunct to Blood Cardioplegia
NCT02867878PHASE2TERMINATEDAdenosin to Rapidly Reverse Left Ventricle Impairment in Takotsubo Syndrome
NCT03032965PHASE2COMPLETEDAdenosine to Assess Complete Conduction Block During Catheter Ablation of Paroxysmal Atrial Fibrillation
NCT03236311PHASE2TERMINATEDA Dose Titration Study to Assess the Effects of SAR407899 in Patients With MVA and/or Persistent Stable Angina Despite Angiographically Successful PCI
NCT04588441PHASE2WITHDRAWNThe ARCTIC Trial: Aerosolized Inhaled Adenosine Treatment in Patients With Acute Respiratory Distress Syndrome (ARDS) Caused by COVID-19
NCT05234307PHASE1RECRUITINGPBF-1129 and Nivolumab for the Treatment of Recurrent or Metastatic Non-Small Cell Lung Cancer

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

477 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
CAFFEINEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA2B, ADORA3
ISTRADEFYLLINEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA2B, ADORA3
REGADENOSONChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA2B, ADORA3
THEOPHYLLINEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA2B, ADORA3
BINODENOSONChEMBLPhase 3ADORA1, ADORA2A, ADORA2B, ADORA3
ROLOFYLLINEChEMBLPhase 3ADORA1, ADORA2A, ADORA2B, ADORA3
TONAPOFYLLINEChEMBLPhase 3ADORA1, ADORA2A, ADORA2B, ADORA3
TOZADENANTChEMBLPhase 3ADORA1, ADORA2A, ADORA2B, ADORA3
TRABODENOSONChEMBLPhase 3ADORA1, ADORA2A, ADORA2B, ADORA3
CIFORADENANTChEMBLPhase 2ADORA1, ADORA2A, ADORA2B, ADORA3
DERENOFYLLINEChEMBLPhase 2ADORA1, ADORA2A, ADORA2B, ADORA3
ENPROFYLLINEChEMBLPhase 2ADORA1, ADORA2A, ADORA2B, ADORA3
IMARADENANTChEMBLPhase 2ADORA1, ADORA2A, ADORA2B, ADORA3
TECADENOSONChEMBLPhase 2ADORA1, ADORA2A, ADORA2B, ADORA3
VIPADENANTChEMBLPhase 2ADORA1, ADORA2A, ADORA2B, ADORA3
FidaxomicinChEMBL + PubChemPhase 4 (approved)ADORA1, ADORA2A, ADORA3
LinagliptinChEMBL + PubChemPhase 4 (approved)ADORA1, ADORA2A, ADORA3
PyrazinamideChEMBL + PubChemPhase 4 (approved)ADORA1, ADORA2A, ADORA3
CLOFARABINEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
CLOTRIMAZOLEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
ECONAZOLEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
EPALRESTATChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
FEDRATINIBChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
MEFLOQUINEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
MICONAZOLEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
NEVIRAPINEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
NIFEDIPINEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
NIMESULIDEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
NISOLDIPINEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
NITAZOXANIDEChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
PENTOSTATINChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
PYRVINIUMChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
RIFAMPINChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
RIFAXIMINChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
SUNITINIBChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
TAMOXIFENChEMBLPhase 4 (approved)ADORA1, ADORA2A, ADORA3
APADENOSONChEMBLPhase 3ADORA1, ADORA2A, ADORA3
DIACEREINChEMBLPhase 3ADORA1, ADORA2A, ADORA3
NAMODENOSONChEMBLPhase 3ADORA1, ADORA2A, ADORA3
ETRUMADENANTChEMBLPhase 2ADORA1, ADORA2A, ADORA2B
METRIFUDILChEMBLPhase 2ADORA1, ADORA2A, ADORA3
SONEDENOSONChEMBLPhase 2ADORA1, ADORA2A, ADORA2B
TOFIMILASTChEMBLPhase 2ADORA1, ADORA2A, ADORA3
AfatinibPubChemApprovedADORA1, ADORA2A, ADORA3
ApixabanPubChemApprovedADORA1, ADORA2A, ADORA3
BinimetinibPubChemApprovedADORA1, ADORA2A, ADORA3
BosentanPubChemApprovedADORA1, ADORA2A, ADORA3
chenodiolPubChemApprovedADORA1, ADORA2A, ADORA3
DihydroergotaminePubChemApprovedADORA1, ADORA2A, ADORA3
FulvestrantPubChemApprovedADORA1, ADORA2A, ADORA3
ImipenemPubChemApprovedADORA1, ADORA2A, ADORA3
PropoxyphenePubChemApprovedADORA1, ADORA2A, ADORA3
ALPIDEMChEMBLPhase 4 (approved)ADORA1, ADORA3
AMPHETAMINEChEMBLPhase 4 (approved)ADORA1, ADORA2A
BALSALAZIDEChEMBLPhase 4 (approved)ADORA2A, ADORA3
BITHIONOLChEMBLPhase 4 (approved)ADORA2A, ADORA3
DAUNORUBICINChEMBLPhase 4 (approved)ADORA2A, ADORA3
ENASIDENIBChEMBLPhase 4 (approved)ADORA1, ADORA3
ERLOTINIBChEMBLPhase 4 (approved)ADORA2A, ADORA3

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot