Apadenoson

HCID 9805430

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Grundinformationen

CAS: 250386-15-3
Standard-SMILES: CCNC(=O)[C@H]1O[C@@H](n2cnc3c(N)nc(C#CCC4CCC(C(=O)OC)CC4)nc32)[C@H](O)[C@@H]1O
InChIKey: FLEVIENZILQUKB-XTWQNQIISA-N
Summenformel: C23H30N6O6
Durchschnittliche Molmasse: 486,5 g/mol

Überblick

Apadenoson is a selective A2a adenosine receptor agonist designed for use as a pharmacologic stress agent in cardiac perfusion imaging studies. It is developed by Bristol-Myers Squibb and is in phase II of clinical trials.

Namen und Bezeichner

Bevorzugter Name: Apadenoson
IUPAC: methyl 4-[3-[6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]prop-2-ynyl]cyclohexane-1-carboxylate
Englischer Name: ATL 146e
Summenformel: C23H30N6O6
Molmasse: 486.52

Namen und Synonyme

Apadenoson250386-15-3StedivazeATL 146eDWH 146eDWH-146eBMS068645Apadenoson [USAN:INN]UNII-BTS1Y6777MBMS-068645BTS1Y6777MBMS 068645

Weitere Namen anzeigen

APADENOSON, ATL146-eApadenoson (Discontinued)Apadenoson,BMS-068645, ATL-146e, DWH-146etrans-4-[3-[6-Amino-9-(N-ethyl--D-ribofuranuronamidosyl)-9H-purin-2-yl]-2-propyn-1-yl]-cyclohexanecarboxylic Acid Methyl EsterCyclohexanecarboxylic acid, 4-[3-[6-amino-9-(N-ethyl-β-D-ribofuranuronamidosyl)-9H-purin-2-yl]-2-propyn-1-yl]-, methyl ester,trans-

CHEMBL1950649ATL-146eApadenoson (USAN)Apadenoson [USAN]methyl 4-[3-[6-amino-9-[(2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purin-2-yl]prop-2-ynyl]cyclohexane-1-carboxylatemethyl trans-4-(3-(6-amino-9-(N-ethyl-b-D-ribofuranosyluronamide)-9H-purin-2-yl)prop-2-ynyl)cyclohexanecarboxylateMethyl trans-4-(3-(6-amino-9-((2R,3R,4S,5S)-5-(ethylcarbamoyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-2-yl)prop-2-yn-1-yl)cyclohexane-1-carboxylateATL146e

Datenbank-Bezeichner

CAS: 250386-15-3
PubChem CID: 9805430
ChEMBL: CHEMBL1950649
UNII: BTS1Y6777M
Nikkaji: J1.523.123H、J2.476.679I

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 0,8
Polarare Oberfläche (TPSA): 175 Å²
H-Brücken-Donoren: 4
H-Brücken-Akzeptoren: 10
Frei drehbare Bindungen: 7
Schwere Atome: 35
Formalladung: 0
Komplexität: 839

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Physikochemische Eigenschaften

Dichte: 1.54 · 1.54±0.1 g/cm3(Predicted)
Löslichkeit: soluble in Methanol
pka: 12.89 · 12.89±0.70(Predicted)
Aggregatzustand: Solid
Farbe: Off-White to Light Beige

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

BMS068645 is designed to selectively stimulate the A2a adenosine receptor responsible for coronary vasodilation. Research to date suggests that this compound could potentially reduce or eliminate side effects associated with currently available pharmacologic stress agents that are not selective for the A2a adenosine receptor.

ATL146e can inhibit neutrophil, macrophage and T cell activation and thereby reduce inflammation caused autoimmune responses. It also inhibits TNF-α and IL-1/3 production, neutrophil accumulation in gastric injury induced by NSAIDS (such as aspirin) without affecting mucosal prostaglandin E2 (PGE2) concentration. The effects of adenosine A2A agonists can be enhanced by type IV phosphodiesterase inhibitors, such as rolipram.