Apadenoson
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Also known as Bms-068645BMS068645DWH-146EStedivaze
Summary
Apadenoson (CHEMBL1950649) is a phase-3 clinical-stage small molecule targeting ADORA1, ADORA2A, and ADORA3.
At a glance
- Status: Max clinical phase 3 (not approved)
- Modality: Small molecule
- Targets: 3 (ADORA1, ADORA2A, ADORA3)
- Clinical trials: 5
- Chemistry: 486.5 Da · C23H30N6O6
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1950649 |
| Name | Apadenoson |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | no |
| PubChem CID | 9805430 |
| Molecular formula | C23H30N6O6 |
| Molecular weight | 486.5 |
| InChIKey | FLEVIENZILQUKB-DMJMAAGCSA-N |
SMILES: CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=C(N=C32)C#CCC4CCC(CC4)C(=O)OC)N)O)O
IUPAC name: methyl 4-[3-[6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]prop-2-ynyl]cyclohexane-1-carboxylate
Also known as: Apadenoson, Bms-068645, BMS-068645, BMS068645, DWH-146E, Stedivaze, APADENOSON, apadenoson
Patent coverage: 20 distinct patent families (37 SureChEMBL compound mentions), from 1 matched compound structure(s). 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).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| ADORA1 | A1 receptor | Agonist | 7.11 | 0.3% | P30542 |
| ADORA2A | A2A receptor | Agonist | 9.3 | 0.4% | P29274 |
| ADORA3 | A3 receptor | Agonist | 7.35 | 0% | P0DMS8 |
Broader ChEMBL bioactivity targets: 3 (assay-derived). Sample: Adenosine receptor A1, Adenosine receptor A2a, Adenosine receptor A3.
Bioactivity
ChEMBL activities: 6 potent at pChembl ≥ 5 of 6 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| ADORA2A | 9.3 | Ki | 0.5 | nM | CHEMBL_ACT_10923784 |
| ADORA2A | 9.3 | Ki | 0.5 | nM | CHEMBL_ACT_14644266 |
| ADORA2A | 9.3 | Ki | 0.5 | nM | CHEMBL_ACT_15210117 |
| ADORA2A | 9.3 | Ki | 0.5 | nM | CHEMBL_ACT_8031723 |
| ADORA3 | 7.35 | Ki | 45 | nM | CHEMBL_ACT_14644307 |
| ADORA1 | 7.11 | Ki | 77 | nM | CHEMBL_ACT_14644293 |
Target pathways
Aggregated over 3 target gene(s): ADORA1, ADORA2A, ADORA3.
Top Reactome pathways
16 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 3 | ADORA1, ADORA2A, ADORA3 |
| Signaling by GPCR | 3 | ADORA1, ADORA2A, ADORA3 |
| Class A/1 (Rhodopsin-like receptors) | 3 | ADORA1, ADORA2A, ADORA3 |
| GPCR downstream signalling | 3 | ADORA1, ADORA2A, ADORA3 |
| Adenosine P1 receptors | 3 | ADORA1, ADORA2A, ADORA3 |
| Nucleotide-like (purinergic) receptors | 3 | ADORA1, ADORA2A, ADORA3 |
| GPCR ligand binding | 3 | ADORA1, ADORA2A, ADORA3 |
| G alpha (i) signalling events | 2 | ADORA1, ADORA3 |
| Signaling by NTRKs | 1 | ADORA2A |
| Activation of TRKA receptors | 1 | ADORA2A |
| NGF-independant TRKA activation | 1 | ADORA2A |
| Signaling by NTRK1 (TRKA) | 1 | ADORA2A |
| Metabolism of proteins | 1 | ADORA2A |
| G alpha (s) signalling events | 1 | ADORA2A |
| Surfactant metabolism | 1 | ADORA2A |
| Signaling by Receptor Tyrosine Kinases | 1 | ADORA2A |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| inflammatory response | 3 |
| signal transduction | 3 |
| G protein-coupled receptor signaling pathway | 3 |
| negative regulation of cell population proliferation | 3 |
| G protein-coupled adenosine receptor signaling pathway | 3 |
| phagocytosis | 2 |
| cell-cell signaling | 2 |
| response to purine-containing compound | 2 |
| vasodilation | 2 |
| excitatory postsynaptic potential | 2 |
| apoptotic signaling pathway | 2 |
| negative regulation of inflammatory response | 2 |
| regulation of norepinephrine secretion | 2 |
| presynaptic modulation of chemical synaptic transmission | 2 |
| temperature homeostasis | 1 |
Indications & clinical
Indications
0 indications (0 at ChEMBL trial phase 4).
Clinical trials
Total trials: 5.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 4 |
| PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00162084 | PHASE3 | TERMINATED | A Study to Examine MPI SPECT Imaging With BMS068645 and Adenosine Compared to Coronary Angiography |
| NCT00380198 | PHASE3 | TERMINATED | A Comparison Study of Apadenoson and Adenosine to Treadmill Exercise Stress. |
| NCT00990327 | PHASE3 | TERMINATED | Study of the Safety and Efficacy of Apadenoson for Detection of Myocardial Perfusion Defects Using SPECT MPI |
| NCT01313572 | PHASE3 | TERMINATED | Study of the Safety and Efficacy of Apadenoson for Detection of Myocardial Perfusion Defects Using SPECT MPI |
| NCT00162071 | PHASE2 | TERMINATED | A Phase II Optimization Study of BMS068645 and Sestamibi Planar Imaging |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No PharmGKB pharmacogenomic data curated for this drug.
Related molecules
Related molecules
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.
472 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| Fidaxomicin | ChEMBL + PubChem | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| Linagliptin | ChEMBL + PubChem | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| Pyrazinamide | ChEMBL + PubChem | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| ADENOSINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| CAFFEINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| CLOFARABINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| ECONAZOLE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| EPALRESTAT | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| FEDRATINIB | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| ISTRADEFYLLINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| MEFLOQUINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| MICONAZOLE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| NEVIRAPINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| NIFEDIPINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| NIMESULIDE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| NISOLDIPINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| NITAZOXANIDE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| PENTOSTATIN | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| PYRVINIUM | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| REGADENOSON | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| RIFAMPIN | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| RIFAXIMIN | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| SUNITINIB | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| TAMOXIFEN | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| THEOPHYLLINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A, ADORA3 |
| BINODENOSON | ChEMBL | Phase 3 | ADORA1, ADORA2A, ADORA3 |
| DIACEREIN | ChEMBL | Phase 3 | ADORA1, ADORA2A, ADORA3 |
| NAMODENOSON | ChEMBL | Phase 3 | ADORA1, ADORA2A, ADORA3 |
| ROLOFYLLINE | ChEMBL | Phase 3 | ADORA1, ADORA2A, ADORA3 |
| TONAPOFYLLINE | ChEMBL | Phase 3 | ADORA1, ADORA2A, ADORA3 |
| TOZADENANT | ChEMBL | Phase 3 | ADORA1, ADORA2A, ADORA3 |
| TRABODENOSON | ChEMBL | Phase 3 | ADORA1, ADORA2A, ADORA3 |
| CIFORADENANT | ChEMBL | Phase 2 | ADORA1, ADORA2A, ADORA3 |
| DERENOFYLLINE | ChEMBL | Phase 2 | ADORA1, ADORA2A, ADORA3 |
| ENPROFYLLINE | ChEMBL | Phase 2 | ADORA1, ADORA2A, ADORA3 |
| IMARADENANT | ChEMBL | Phase 2 | ADORA1, ADORA2A, ADORA3 |
| METRIFUDIL | ChEMBL | Phase 2 | ADORA1, ADORA2A, ADORA3 |
| TECADENOSON | ChEMBL | Phase 2 | ADORA1, ADORA2A, ADORA3 |
| TOFIMILAST | ChEMBL | Phase 2 | ADORA1, ADORA2A, ADORA3 |
| VIPADENANT | ChEMBL | Phase 2 | ADORA1, ADORA2A, ADORA3 |
| Afatinib | PubChem | Approved | ADORA1, ADORA2A, ADORA3 |
| Apixaban | PubChem | Approved | ADORA1, ADORA2A, ADORA3 |
| Binimetinib | PubChem | Approved | ADORA1, ADORA2A, ADORA3 |
| Bosentan | PubChem | Approved | ADORA1, ADORA2A, ADORA3 |
| chenodiol | PubChem | Approved | ADORA1, ADORA2A, ADORA3 |
| Dihydroergotamine | PubChem | Approved | ADORA1, ADORA2A, ADORA3 |
| Fulvestrant | PubChem | Approved | ADORA1, ADORA2A, ADORA3 |
| Imipenem | PubChem | Approved | ADORA1, ADORA2A, ADORA3 |
| Propoxyphene | PubChem | Approved | ADORA1, ADORA2A, ADORA3 |
| ALPIDEM | ChEMBL | Phase 4 (approved) | ADORA1, ADORA3 |
| AMPHETAMINE | ChEMBL | Phase 4 (approved) | ADORA1, ADORA2A |
| BALSALAZIDE | ChEMBL | Phase 4 (approved) | ADORA2A, ADORA3 |
| BITHIONOL | ChEMBL | Phase 4 (approved) | ADORA2A, ADORA3 |
| DAUNORUBICIN | ChEMBL | Phase 4 (approved) | ADORA2A, ADORA3 |
| ENASIDENIB | ChEMBL | Phase 4 (approved) | ADORA1, ADORA3 |
| ERLOTINIB | ChEMBL | Phase 4 (approved) | ADORA2A, ADORA3 |
| ETHINYL ESTRADIOL | ChEMBL | Phase 4 (approved) | ADORA2A, ADORA3 |
| GENTIAN VIOLET | ChEMBL | Phase 4 (approved) | ADORA2A, ADORA3 |
Related Atlas pages
- Genes: ADORA1, ADORA2A, ADORA3
- Drugs: Fidaxomicin, Linagliptin, Pyrazinamide, Adenosine, Caffeine, Clofarabine, Clotrimazole, Diethylstilbestrol, Econazole, Epalrestat, Fedratinib, Istradefylline, Mefloquine, Miconazole, Nevirapine, Nifedipine, Nimesulide, Nisoldipine, Nitazoxanide, Pentostatin, Pyrvinium, Regadenoson, Rifampin, Rifaximin, Sunitinib, Tamoxifen, Theophylline, Binodenoson, Diacerein, Namodenoson, Rolofylline, Tonapofylline, Tozadenant, Trabodenoson, Afatinib, Apixaban, Binimetinib, Bosentan, chenodiol, Dihydroergotamine, Fulvestrant, Imipenem, Propoxyphene, Alpidem, Amphetamine, Balsalazide, Bithionol, Daunorubicin, Enasidenib, Erlotinib, Ethinyl Estradiol