Tecadenoson
Basic information
- CAS
204512-90-3- Standard SMILES
OC[C@H]1O[C@@H](n2cnc3c(N[C@@H]4CCOC4)ncnc32)[C@H](O)[C@@H]1O- InChIKey
OESBDSFYJMDRJY-BAYCTPFLSA-N- Molecular formula
- C14H19N5O5
- Average molar mass
- 337.33 g/mol
- Monoisotopic mass
- 337.13861872
Overview
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.
Names & identifiers
- Preferred name
- Tecadenoson
- IUPAC
- (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[[(3R)-oxolan-3-yl]amino]purin-9-yl]oxolane-3,4-diol
- English name
- Tecadenoson
- Molecular formula
- C14H19N5O5
- Molecular weight
- 337.33
Names & synonyms
Tecadenoson204512-90-3CVT-510GZ1X96601Z(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[[(3R)-oxolan-3-yl]amino]purin-9-yl]oxolane-3,4-diolN-(3-Tetrahydrofuranyl)-6-aminopurine ribosideDTXSID80174415tecadenosonum(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(((3R)-oxolan-3-yl)amino)purin-9-yl)oxolane-3,4-diolRefChem:891270DTXCID8096906(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(((3R)-oxolan-3-yl)amino)-9H-purin-9-yl)oxolane-3,4-diol
Show more names
TecadenosoTecadenoson, 10 mM in DMSON6-[3(R)-Tetrahydrofuranyl]adenosineAdenosine, N-[(3R)-tetrahydro-3-furanyl]-Inhibitor,P1 receptor,Tecadenoson,Adenosine Receptor,CVT510,CVT 510,inhibit
MFCD08690887(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(((R)-tetrahydrofuran-3-yl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diolCHEMBL392149DB04954Adenosine, N-(3R)-tetrahydro-3-furanyl)-CS-0016174BDBM502247662-(6-(((3R)Oxolan-3-yl)amino)purin-9-yl)(2R,4S,3R,5R)-5-(hydroxymethyl)oxolane-3,4-diol
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 135 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 446
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 704.9 · 704.9±70.0 °C(Predicted)
- Density
- 1.89 · 1.89±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C(protect from light)
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: Partially soluble; PBS (pH 7.2): 3 mg/ml
- form
- A crystalline solid
- pka
- 13.11 · 13.11±0.70(Predicted)
- color
- White to off-white
- FDA UNII
- 1 X96601Z · GZ1X96601Z
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
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.
MeSH Pharmacological ClassificationCompounds that bind to and stimulate PURINERGIC P1 RECEPTORS.
Applications
DescriptionTecadenoson is an analog of adenosine. Tecadenoson works by activating two types of receptors: A1 and A2A. Activation of these receptors leads to increased blood supply, which improves symptoms in patients with chronic obstructive pulmonary disease. Tecadenoson has also been shown to reduce inflammation and improve lung function in animal models of asthma. Tecadenoson is not active against bacterial infections or viral infections, but is effective against autoimmune diseases such as lupus erythematosus, rheumatoid arthritis, and vasculitis.
UsesTreatment of paroxysmal supraventricular tachycardia and rate control in atrial fibrillation and atrial flutter.
Related reactions
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Compound notes
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