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Apadenoson

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Identification

Generic Name
Apadenoson
DrugBank Accession Number
DB05009
Background

Apadenoson is a selective A2a adenosine receptor agonist designed for use as a pharmacologic stress agent in cardiac perfusion imaging studies. It is developed by Bristol-Myers Squibb and is in phase II of clinical trials.

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 486.529
Monoisotopic: 486.22268271
Chemical Formula
C23H30N6O6
Synonyms
  • Apadenoson
External IDs
  • BMS-068645
  • BMS068645
  • DWH-146E
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Pharmacology

Indication

Investigated for use/treatment in cardiovascular disorders and inflammatory disorders (unspecified).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

BMS068645 is designed to selectively stimulate the A2a adenosine receptor responsible for coronary vasodilation. Research to date suggests that this compound could potentially reduce or eliminate side effects associated with currently available pharmacologic stress agents that are not selective for the A2a adenosine receptor.

TargetActionsOrganism
AAdenosine receptor A2a
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Not Available
Direct Parent
Purine nucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Tetrahydrofurans / Methyl esters / Heteroaromatic compounds / Secondary carboxylic acid amides / Secondary alcohols
show 10 more
Substituents
1,2-diol / 6-aminopurine / Alcohol / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonyl group
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
BTS1Y6777M
CAS number
250386-15-3
InChI Key
FLEVIENZILQUKB-XTWQNQIISA-N
InChI
InChI=1S/C23H30N6O6/c1-3-25-21(32)18-16(30)17(31)22(35-18)29-11-26-15-19(24)27-14(28-20(15)29)6-4-5-12-7-9-13(10-8-12)23(33)34-2/h11-13,16-18,22,30-31H,3,5,7-10H2,1-2H3,(H,25,32)(H2,24,27,28)/t12-,13-,16-,17+,18-,22+/m0/s1
IUPAC Name
methyl (1r,4r)-4-(3-{6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-9H-purin-2-yl}prop-2-yn-1-yl)cyclohexane-1-carboxylate
SMILES
CCNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(N=C2N)C#CC[C@H]1CC[C@@H](CC1)C(=O)OC

References

General References
  1. Cerqueira MD: Advances in pharmacologic agents in imaging: new A2A receptor agonists. Curr Cardiol Rep. 2006 Mar;8(2):119-22. [Article]
PubChem Compound
9805430
PubChem Substance
175426929
ChemSpider
28490919
BindingDB
50364063
ChEMBL
CHEMBL1950649

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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3TerminatedDiagnosticCardiovascular Disease (CVD) / Ischemic Heart Disease1somestatusstop reasonjust information to hide
3TerminatedDiagnosticCoronary Artery Disease (CAD)3somestatusstop reasonjust information to hide
2TerminatedDiagnosticCardiovascular Disease (CVD) / Ischemic Heart Disease1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.116 mg/mLALOGPS
logP1.3ALOGPS
logP0.89Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.39Chemaxon
pKa (Strongest Basic)1.09Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area174.71 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity121.62 m3·mol-1Chemaxon
Polarizability51.82 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6699
Blood Brain Barrier-0.8495
Caco-2 permeable-0.7314
P-glycoprotein substrateSubstrate0.6414
P-glycoprotein inhibitor INon-inhibitor0.806
P-glycoprotein inhibitor IIInhibitor0.7197
Renal organic cation transporterNon-inhibitor0.9358
CYP450 2C9 substrateNon-substrate0.8675
CYP450 2D6 substrateNon-substrate0.863
CYP450 3A4 substrateSubstrate0.5298
CYP450 1A2 substrateNon-inhibitor0.861
CYP450 2C9 inhibitorNon-inhibitor0.7137
CYP450 2D6 inhibitorNon-inhibitor0.882
CYP450 2C19 inhibitorNon-inhibitor0.7195
CYP450 3A4 inhibitorNon-inhibitor0.6549
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7451
Ames testNon AMES toxic0.6989
CarcinogenicityNon-carcinogens0.8713
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5995 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9828
hERG inhibition (predictor II)Inhibitor0.6507
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002r-0000900000-f6d74f3b3cf19f1d2617
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0039000000-a5df172ea58d0ec50fe6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-1019800000-ebefb67ccb8d2a9d92d2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01pa-1004900000-262dda48e359156c62e5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-4219500000-33dca23b24045103aa76
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-022j-0749400000-003dfe179adf942c20a9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-198.70937
predicted
DeepCCS 1.0 (2019)
[M+H]+200.53427
predicted
DeepCCS 1.0 (2019)
[M+Na]+206.14009
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Adenosine receptor A2a
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Receptor for adenosine (By similarity). The activity of this receptor is mediated by G proteins which activate adenylyl cyclase (By similarity)
Specific Function
alpha-actinin binding
Gene Name
ADORA2A
Uniprot ID
P29274
Uniprot Name
Adenosine receptor A2a
Molecular Weight
44706.925 Da
References
  1. Cerqueira MD: Advances in pharmacologic agents in imaging: new A2A receptor agonists. Curr Cardiol Rep. 2006 Mar;8(2):119-22. [Article]
  2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at October 21, 2007 22:23 / Updated at August 26, 2024 19:23