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Identification
NameTecadenoson
Accession NumberDB04954
TypeSmall Molecule
GroupsInvestigational
DescriptionTecadenoson is a novel selective A1 adenosine receptor agonist that is currently being evaluated for the conversion of paroxysmal supraventricular tachycardia (PSVT) to sinus rhythm. It is being developed by CV Therapeutics, Inc.
Structure
Thumb
SynonymsNot Available
External Identifiers
  • CVT-510
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIGZ1X96601Z
CAS number204512-90-3
WeightAverage: 337.3312
Monoisotopic: 337.138618743
Chemical FormulaC14H19N5O5
InChI KeyOESBDSFYJMDRJY-BAYCTPFLSA-N
InChI
InChI=1S/C14H19N5O5/c20-3-8-10(21)11(22)14(24-8)19-6-17-9-12(15-5-16-13(9)19)18-7-1-2-23-4-7/h5-8,10-11,14,20-22H,1-4H2,(H,15,16,18)/t7-,8-,10-,11-,14-/m1/s1
IUPAC Name
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(3R)-oxolan-3-yl]amino}-9H-purin-9-yl)oxolane-3,4-diol
SMILES
OC[[email protected]]1O[[email protected]]([[email protected]](O)[C@@H]1O)N1C=NC2=C(N[C@@H]3CCOC3)N=CN=C12
Pharmacology
IndicationInvestigated for use/treatment in arrhythmia and atrial fibrillation.
Structured Indications Not Available
PharmacodynamicsTecadenoson is a novel A1 adenosine receptor stimulator. Adenosine is a naturally occurring compound that stimulates all adenosine receptor subtypes in the body, including the A2 adenosine receptor which lowers blood pressure. In non-clinical trials, tecadenoson selectively stimulated the A1 adenosine receptor in the AV node and slowed the speed of electrical conduction across the AV node, reducing the number of electrical impulses that reached the ventricle, without affecting blood pressure. Clinical studies to date with intravenous tecadenoson suggest that it may slow the speed of AV nodal conduction by selectively stimulating the A1 adenosine receptor, and may avoid blood pressure lowering by not stimulating the A2 adenosine receptor. Thus, it may be possible to use intravenous tecadenoson to convert patients from PSVT to normal sinus rhythm without lowering blood pressure or causing adverse events related to vasodilitation such as flushing, palpitations or headache.
Mechanism of actionTecadenoson selectively stimulates the A1 adenosine receptor. Stimulation of the A1 adenosine receptor slows the conduction of electrical impulses in the AV node of the heart, a region that controls the transmission of electrical impulses from the atria to the ventricles.
TargetKindPharmacological actionActionsOrganismUniProt ID
Adenosine receptor A1ProteinunknownNot AvailableHumanP30542 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Peterman C, Sanoski CA: Tecadenoson: a novel, selective A1 adenosine receptor agonist. Cardiol Rev. 2005 Nov-Dec;13(6):315-21. [PubMed:16230891 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9324
Blood Brain Barrier+0.5693
Caco-2 permeable-0.8302
P-glycoprotein substrateSubstrate0.6273
P-glycoprotein inhibitor INon-inhibitor0.9216
P-glycoprotein inhibitor IINon-inhibitor0.9405
Renal organic cation transporterNon-inhibitor0.8958
CYP450 2C9 substrateNon-substrate0.8232
CYP450 2D6 substrateNon-substrate0.7954
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.9162
CYP450 2C9 inhibitorNon-inhibitor0.9456
CYP450 2D6 inhibitorNon-inhibitor0.9561
CYP450 2C19 inhibitorNon-inhibitor0.9311
CYP450 3A4 inhibitorNon-inhibitor0.9553
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9525
Ames testNon AMES toxic0.6803
CarcinogenicityNon-carcinogens0.9063
BiodegradationNot ready biodegradable0.9393
Rat acute toxicity2.0840 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8826
hERG inhibition (predictor II)Non-inhibitor0.731
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.22 mg/mLALOGPS
logP-0.47ALOGPS
logP-1.9ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)4.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.78 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.3 m3·mol-1ChemAxon
Polarizability33.24 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine ribonucleoside
  • 6-alkylaminopurine
  • N-glycosyl compound
  • Glycosyl compound
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Purine nucleoside binding
Specific Function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
ADORA1
Uniprot ID:
P30542
Molecular Weight:
36511.325 Da
References
  1. Peterman C, Sanoski CA: Tecadenoson: a novel, selective A1 adenosine receptor agonist. Cardiol Rev. 2005 Nov-Dec;13(6):315-21. [PubMed:16230891 ]
  2. Ellenbogen KA, O'Neill G, Prystowsky EN, Camm JA, Meng L, Lieu HD, Jerling M, Shreeniwas R, Belardinelli L, Wolff AA: Trial to evaluate the management of paroxysmal supraventricular tachycardia during an electrophysiology study with tecadenoson. Circulation. 2005 Jun 21;111(24):3202-8. Epub 2005 Jun 13. [PubMed:15956124 ]
  3. Prystowsky EN, Niazi I, Curtis AB, Wilber DJ, Bahnson T, Ellenbogen K, Dhala A, Bloomfield DM, Gold M, Kadish A, Fogel RI, Gonzalez MD, Belardinelli L, Shreeniwas R, Wolff AA: Termination of paroxysmal supraventricular tachycardia by tecadenoson (CVT-510), a novel A1-adenosine receptor agonist. J Am Coll Cardiol. 2003 Sep 17;42(6):1098-102. [PubMed:13678937 ]
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Drug created on October 21, 2007 16:23 / Updated on August 17, 2016 12:24