Tecadenoson

Identification

Name
Tecadenoson
Accession Number
DB04954
Type
Small Molecule
Groups
Investigational
Description

Tecadenoson 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
Synonyms
Not Available
External IDs
CVT-510
Categories
UNII
GZ1X96601Z
CAS number
204512-90-3
Weight
Average: 337.3312
Monoisotopic: 337.138618743
Chemical Formula
C14H19N5O5
InChI Key
OESBDSFYJMDRJY-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

Pharmacology

Indication

Investigated for use/treatment in arrhythmia and atrial fibrillation.

Structured Indications
Not Available
Pharmacodynamics

Tecadenoson 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 action

Tecadenoson 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.

TargetActionsOrganism
UAdenosine receptor A1Not AvailableHuman
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
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

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
PubChem Compound
158795
PubChem Substance
175426918
ChemSpider
139685
BindingDB
50224766
ChEMBL
CHEMBL392149

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentNonvalvular Atrial Fibrillation1

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 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

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
6-alkylaminopurines / Glycosylamines / Secondary alkylarylamines / Aminopyrimidines and derivatives / Imidolactams / Monosaccharides / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols
show 6 more
Substituents
Purine nucleoside / Glycosyl compound / N-glycosyl compound / 6-alkylaminopurine / 6-aminopurine / Imidazopyrimidine / Purine / Aminopyrimidine / Secondary aliphatic/aromatic amine / Imidolactam
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Adenosine receptor A1
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
Uniprot Name
Adenosine receptor A1
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]

Drug created on October 21, 2007 16:23 / Updated on December 01, 2017 15:34