Apadenoson

HCID 9805430

기본 정보

CAS: 250386-15-3
표준 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
분자식: C23H30N6O6
평균 분자량: 486.5 g/mol

개요

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.

이름 및 식별자

우선 이름: 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
영어명: ATL 146e
분자식: C23H30N6O6
분자량: 486.52

이름 및 동의어

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

이름 더 보기

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: 0.8
극성 표면적: 175 Å²
수소 결합 공여자 수: 4
수소 결합 수용자 수: 10
회전 가능 결합 수: 7
무거운 원자 수: 35
형식 전하: 0
복잡도: 839

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15

물리화학적 성질

밀도: 1.54 · 1.54±0.1 g/cm3(Predicted)
용해도: 메탄올에 용해됨
산도 계수 (pKa): 12.89 · 12.89±0.70(Predicted)
물리적 상태: 고체
색상: 미색부터 밝은 베이지까지

화학 및 산업

약리 정보

Mechanism of Action · 2건

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.