Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H19N5O5 |
Molecular Weight | 337.3312 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=CN=C3N[C@@H]4CCOC4
InChI
InChIKey=OESBDSFYJMDRJY-BAYCTPFLSA-N
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16230891Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB04954 | https://www.ncbi.nlm.nih.gov/pubmed/23388705 | https://www.ncbi.nlm.nih.gov/pubmed/23989533
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16230891
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB04954 | https://www.ncbi.nlm.nih.gov/pubmed/23388705 | https://www.ncbi.nlm.nih.gov/pubmed/23989533
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. 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 Atrioventricular node (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 vasodilation such as flushing, palpitations or a headache.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23388705 |
11.0 µM [Ki] | ||
Target ID: CHEMBL3509606 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23388705 |
189.0 µM [Ki] | ||
Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17967536 |
65.0 nM [Ki] | ||
Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17933541 |
6390.0 µM [Ki] | ||
Target ID: CHEMBL255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17933541 |
227.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Low [IC50 239 uM] | ||||
moderate [IC50 190 uM] | ||||
moderate [IC50 200 uM] | ||||
yes [IC50 12 uM] | ||||
yes [IC50 41 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major [Km 24 uM] | ||||
minor | ||||
no | ||||
no | ||||
no |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23989533
Twenty-one patients (age 58 ± 7 years, 13 men) with AF were randomly assigned to either 75, 150, or 300 μg intravenous tecadenoson. Tecadenoson was administered alone (Dose Period 1) and in combination (Dose Period 2) with esmolol (100 μg/kg/min for 10 min then 50 μg/kg/min for 50 min).
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14647532
Transport of [3H]tecadenoson was assessed at room temperature (RT) with a high-throughput assay. Yeast were grown in CMM/GLU to an optical density (OD)600 of 0.8–1.2, washed three times with fresh CMM/GLU (pH 7.4), and re-suspended to an OD600 of 4 in CMM/GLU (pH 7.4). For tecadenoson transportability assays, uptake of 1 mM [3H]tecadenoson was measured alone or with 10 mM nonradioactive uridine. The transport assays were initiated by adding an equal volume of yeast suspension at OD600 = 4 to each of the individual wells of the preloaded 96-well plates, which were placed on the semi-automated cell harvester. At graded time intervals, groups of transport reactions (usually 24) were terminated simultaneously by harvesting yeast on glass-fiber filters (Skatron Instruments) with continued washing with demineralized water to remove unincorporated permeant. The filter discs with yeast corresponding to a particular transport assay were placed into individual scintillation counting vials (1 disc/vial) to which 5 ml scintillation counting fluid (EcoLite; ICN Biomedical Inc., Aurora, OH) was added. Scintillation vials were allowed to sit at RT overnight with shaking before analysis.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29707
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MM-91
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204512-90-3
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8179
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GZ1X96601Z
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m10503
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158795
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C77980
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300000034428
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CHEMBL392149
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DTXSID80174415
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DB04954
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ACTIVE MOIETY