Apadenoson

Identification

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Name
Apadenoson
Accession Number
DB05009
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
BMS-068645 / BMS068645 / DWH-146E
Categories
UNII
BTS1Y6777M
CAS number
250386-15-3
Weight
Average: 486.529
Monoisotopic: 486.22268271
Chemical Formula
C23H30N6O6
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

Pharmacology

Indication

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

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
UAdenosine receptor A2aNot AvailableHumans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:16524538]
External Links
PubChem Compound
9805430
PubChem Substance
175426929
ChemSpider
28490919
BindingDB
50364063
ChEMBL
CHEMBL1950649

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedDiagnosticCardiovascular Disease (CVD) / Ischaemic Heart Diseases1
3TerminatedDiagnosticCoronary Artery Disease2
3TerminatedDiagnosticHeart Diseases / Ischaemic Heart Diseases1

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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Purine nucleoside / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Imidazopyrimidine / Purine / Aminopyrimidine / N-substituted imidazole / Imidolactam / Pyrimidine
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Adenosine receptor A2a
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
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. [PubMed:16524538]

Drug created on October 21, 2007 16:23 / Updated on May 01, 2019 09:52