Binodenoson

Identification

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Name
Binodenoson
Accession Number
DB04853
Type
Small Molecule
Groups
Investigational
Description

Binodenoson is a pharmacologic stress agent specific to the only adenosine receptor necessary for increased cardiac blood flow, the A2A receptor. This specificity allows Binodenoson to deliver - in a single injection - a more effective dose of medication with fewer side effects than current treatments, which typically require a 15-20 minute infusion.

Structure
Thumb
Synonyms
  • 2-((Cyclohexylmethylene)hydrazino)adenosine
  • Binodenoson
External IDs
MRE 0470 / MRE-0470 / MRE0470 / SHA-174 / WRC 0470 / WRC-0470
Categories
UNII
LJA4M1L5LG
CAS number
144348-08-3
Weight
Average: 391.4249
Monoisotopic: 391.196802323
Chemical Formula
C17H25N7O4
InChI Key
XJFMHMFFBSOEPR-DNZQAUTHSA-N
InChI
InChI=1S/C17H25N7O4/c18-14-11-15(22-17(21-14)23-20-6-9-4-2-1-3-5-9)24(8-19-11)16-13(27)12(26)10(7-25)28-16/h6,8-10,12-13,16,25-27H,1-5,7H2,(H3,18,21,22,23)/b20-6+/t10-,12-,13-,16-/m1/s1
IUPAC Name
(2R,3R,4S,5R)-2-{6-amino-2-[(E)-2-(cyclohexylmethylidene)hydrazin-1-yl]-9H-purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=C(N\N=C\C3CCCCC3)N=C12

Pharmacology

Indication

For cardiac pharmacologic stress SPECT imaging, which is used to diagnose coronary artery disease.

Pharmacodynamics

Binodenoson, a novel cardiovascular disease diagnostic, is a adenosine A2A receptor agonist in development for cardiac pharmacologic stress SPECT imaging, which is used to diagnose coronary artery disease.

Mechanism of action

Binodenoson is a highly selective adenosine A2A receptor agonist. The adenosine A2A receptor is necessary for increased cardiac blood flow, and specificity to this particular receptor allows binodenoson to deliver, in a single injection, a more effective dose of medication with fewer side effects than current treatments, which typically require a 15-20 minute infusion. Cardiac stress tests allow physicians to identify the presence of cardiovascular disease by examining the flow of blood through the heart.

TargetActionsOrganism
UAdenosine receptor A2aNot AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

10 ± 4 minutes

Clearance
Not Available
Toxicity
Not Available
Affected organisms
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

References

General References
  1. Iskandrian AE: A new generation of coronary vasodilators in stress perfusion imaging. Am J Cardiol. 2007 Jun 1;99(11):1619-20. Epub 2007 Apr 18. [PubMed:17531594]
  2. Barrett RJ, Lamson MJ, Johnson J, Smith WB: Pharmacokinetics and safety of binodenoson after intravenous dose escalation in healthy volunteers. J Nucl Cardiol. 2005 Mar-Apr;12(2):166-71. [PubMed:15812370]
External Links
KEGG Drug
D03120
PubChem Compound
9576912
PubChem Substance
175426864
ChemSpider
7851353
BindingDB
50230152
ChEMBL
CHEMBL1950554

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedDiagnosticCoronary Artery Disease2

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 Solubility1.14 mg/mLALOGPS
logP1.41ALOGPS
logP0.46ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)10.99ChemAxon
pKa (Strongest Basic)4.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area163.93 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.74 m3·mol-1ChemAxon
Polarizability40.99 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9823
Blood Brain Barrier+0.8625
Caco-2 permeable-0.7202
P-glycoprotein substrateNon-substrate0.5957
P-glycoprotein inhibitor INon-inhibitor0.8125
P-glycoprotein inhibitor IINon-inhibitor0.9146
Renal organic cation transporterNon-inhibitor0.8079
CYP450 2C9 substrateNon-substrate0.876
CYP450 2D6 substrateNon-substrate0.8148
CYP450 3A4 substrateSubstrate0.52
CYP450 1A2 substrateInhibitor0.5408
CYP450 2C9 inhibitorNon-inhibitor0.8838
CYP450 2D6 inhibitorNon-inhibitor0.9271
CYP450 2C19 inhibitorNon-inhibitor0.8762
CYP450 3A4 inhibitorNon-inhibitor0.8453
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9666
Ames testNon AMES toxic0.5108
CarcinogenicityNon-carcinogens0.8467
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3667 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8239
hERG inhibition (predictor II)Non-inhibitor0.5924
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 / Pentoses / Aminopyrimidines and derivatives / Imidolactams / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Hydrazones
show 6 more
Substituents
Purine nucleoside / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Pentose monosaccharide / Purine / Imidazopyrimidine / Aminopyrimidine / N-substituted imidazole / Monosaccharide
show 22 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. Hodgson JM, Dib N, Kern MJ, Bach RG, Barrett RJ: Coronary circulation responses to binodenoson, a selective adenosine A2A receptor agonist. Am J Cardiol. 2007 Jun 1;99(11):1507-12. Epub 2007 Apr 16. [PubMed:17531571]
  2. 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 18, 2007 17:25 / Updated on September 02, 2019 18:06