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Apadenoson
Identification
- Name
- Apadenoson
- Accession Number
- DB05009
- 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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Apadenoson (DB05009)
- Weight
- Average: 486.529
Monoisotopic: 486.22268271 - Chemical Formula
- C23H30N6O6
- Synonyms
- Not Available
- External IDs
- BMS-068645
- BMS068645
- DWH-146E
Pharmacology
- Indication
Investigated for use/treatment in cardiovascular disorders and inflammatory disorders (unspecified).
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism UAdenosine receptor A2a Not Available 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
Learn about our commercial Adverse Effects data.
Learn More- 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
Products
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
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)[[email protected]]1O[[email protected]]([[email protected]](O)[[email protected]@H]1O)N1C=NC2=C1N=C(N=C2N)C#CC[[email protected]]1CC[[email protected]@H](CC1)C(=O)OC
References
- General References
- 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
Phase Status Purpose Conditions Count 3 Terminated Diagnostic Coronary Artery Disease (CAD) 3 3 Terminated Diagnostic Heart Diseases / Ischemic Heart Disease 1 2 Terminated Diagnostic Cardiovascular Heart Disease / Ischemic Heart Disease 1
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
Property Value Source Water Solubility 0.116 mg/mL ALOGPS logP 1.3 ALOGPS logP 0.89 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 12.39 ChemAxon pKa (Strongest Basic) 1.09 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 174.71 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 121.62 m3·mol-1 ChemAxon Polarizability 51.82 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6699 Blood Brain Barrier - 0.8495 Caco-2 permeable - 0.7314 P-glycoprotein substrate Substrate 0.6414 P-glycoprotein inhibitor I Non-inhibitor 0.806 P-glycoprotein inhibitor II Inhibitor 0.7197 Renal organic cation transporter Non-inhibitor 0.9358 CYP450 2C9 substrate Non-substrate 0.8675 CYP450 2D6 substrate Non-substrate 0.863 CYP450 3A4 substrate Substrate 0.5298 CYP450 1A2 substrate Non-inhibitor 0.861 CYP450 2C9 inhibitor Non-inhibitor 0.7137 CYP450 2D6 inhibitor Non-inhibitor 0.882 CYP450 2C19 inhibitor Non-inhibitor 0.7195 CYP450 3A4 inhibitor Non-inhibitor 0.6549 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7451 Ames test Non AMES toxic 0.6989 Carcinogenicity Non-carcinogens 0.8713 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5995 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9828 hERG inhibition (predictor II) Inhibitor 0.6507
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- 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
- 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 June 12, 2020 10:52
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