Evodenoson
Basic information
- CAS
844873-47-8- Standard SMILES
COC(=O)N1CCC(CC#Cc2nc(N)c3ncn([C@@H]4O[C@H](C(=O)NC5CC5)[C@@H](O)[C@H]4O)c3n2)CC1- InChIKey
SQJXTUJMBYVDBB-RQXXJAGISA-N- Molecular formula
- C23H29N7O6
- Average molar mass
- 499.5 g/mol
- Monoisotopic mass
- 499.21793167
Overview
Evodenoson has been used in trials studying the treatment of Open-angle Glaucoma and Ocular Hypertension.
Names & identifiers
- Preferred name
- Evodenoson
- IUPAC
- methyl 4-[3-[6-amino-9-[(2R,3R,4S,5S)-5-(cyclopropylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]prop-2-ynyl]piperidine-1-carboxylate
- English name
- Evodenoson
- Molecular formula
- C23H29N7O6
- Molecular weight
- 499.52
Names & synonyms
EVODENOSON844873-47-8ATL-313ATL313DE-112ATL 313HZ03U10J2Zmethyl 4-[3-[6-amino-9-[(2R,3R,4S,5S)-5-(cyclopropylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]prop-2-ynyl]piperidine-1-carboxylateDTXSID40233476evodenosonummethyl 4-(3-(6-amino-9-((2R,3R,4S,5S)-5-(cyclopropylcarbamoyl)-3,4-dihydroxyoxolan-2-yl)-9H-purin-2-yl)prop-2-yn-1-yl)piperidine-1-carboxylatemethyl 4-(3-(6-amino-9-((2R,3R,4S,5S)-5-(cyclopropylcarbamoyl)-3,4-dihydroxyoxolan-2-yl)purin-2-yl)prop-2-ynyl)piperidine-1-carboxylate
Show more names
DE1121-Piperidinecarboxylic acid, 4-[3-[6-amino-9-(N-cyclopropyl-β-D-ribofuranuronamidosyl)-9H-purin-2-yl]-2-propyn-1-yl]-, methyl estermethyl 4-(3-(6-amino-9-((2R,3R,4S,5S)-5-(cyclopropylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)prop-2-yn-1-yl)piperidine-1-carboxylatemethyl 4-(3-(6-amino-9-((2R,3S,4R,5S)-5-(cyclopropylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)prop-2-yn-1-yl)piperidine-1-carboxylate
methyl 4-(3-{6-amino-9-[(2R,3R,4S,5S)-5-(cyclopropylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-9H-purin-2-yl}prop-2-yn-1-yl)piperidine-1-carboxylateRefChem:139676Atl313, de-112DTXCID40155967Evodenoson [USAN:INN]UNII-HZ03U10J2ZDE 112EVODENOSON [INN]
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 178 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 6
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 898
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 131.6 · 131.6-134.9 °C
- Density
- 1.67 · 1.67±0.1 g/cm3(Predicted)
- form
- Solid
- pka
- 12.84 · 12.84±0.70(Predicted)
- color
- White to off-white
- FDA UNII
- 3 U10J2Z · HZ03U10J2Z
Chemistry & industry
Applications
UsesEvodenoson is a selective agonist of the A2A adenosine receptor. Evodenoson’s primary actions include reducing inflammatory responses, decreasing intestinal fluid secretion, edema, tissue damage, and neutrophil infiltration induced by Clostridium difficile toxin A. Evodenoson’s protective effect is achieved by reducing myeloperoxidase (MPO) and adenosine deaminase (ADA) activities, and by lowering the production of tumor necrosis factor-alpha (TNF-α)[1].
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Compound notes
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