APADENOSON

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H30N6O6
Molecular Weight	486.5209
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=C(N=C3N)C#CC[C@H]4CC[C@@H](CC4)C(=O)OC

InChI

InChIKey=FLEVIENZILQUKB-XTWQNQIISA-N

InChI=1S/C23H30N6O6/c1-3-25-21(32)18-16(30)17(31)22(35-18)29-11-26-15-19(24)27-14(28-20(15)29)6-4-5-12-7-9-13(10-8-12)23(33)34-2/h11-13,16-18,22,30-31H,3,5,7-10H2,1-2H3,(H,25,32)(H2,24,27,28)/t12-,13-,16-,17+,18-,22+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://adisinsight.springer.com/drugs/800013850 | https://www.pharmacodia.com/yaodu/html/v1/chemicals/4f7e82050e79d3f6a24897b6413cb90f.html | https://www.ncbi.nlm.nih.gov/pubmed/17280881

Apadenoson (BMS-068645) is a selective adenosine 2A agonist that contains a methyl ester group which undergoes esterase hydrolysis to its acid metabolite. Apadenoson had been in phase III clinical trials by Forest (now a part of Allergan) for the treatment of coronary artery disease. However, this study has been terminated.

Originator

Approval Year

PubMed

Title	Date	PubMed
Selective A(2A) adenosine receptor activation reduces skin pressure ulcer formation and inflammation.	2001 Jul	11406470
Adenosine A2A receptor activation decreases reperfusion injury associated with high-flow reperfusion.	2002 Nov	12407381
Influence of propranolol, enalaprilat, verapamil, and caffeine on adenosine A(2A)-receptor-mediated coronary vasodilation.	2002 Nov 6	12427424
Adenosine receptors as therapeutic targets.	2006 Mar	16518376

Patents

Sample Use Guides

In Vivo Use Guide

Coronary artery disease: Apadenoson single bolus IV injection 100 or 150 ug

Route of Administration: Intravenous

Name

Type

Language

APADENOSON

Official Name

English

METHYL TRANS-4-(3(6-AMINO-9-(N-ETHYL-.BETA.-D-RIBOFURANOSYLURONAMIDE)-9H-PURIN-2-YL)PROP-2-YNYL)CYCLOHEXANECARBOXYLATE

Systematic Name

English

BMS-068645

Code

English

Apadenoson [WHO-DD]

Common Name

English

BMS068645

Code

English

APADENOSON [USAN]

Common Name

English

CYCLOHEXANECARBOXYLIC ACID, 4-(3(6-AMINO-9-(N-ETHYL-.BETA.-D-RIBOFURANURONAMIDOSYL)-9H-PURIN-2-YL)-2-PROPNYL)-, METHYL ESTER, TRANS-

Systematic Name

English

DWH-146E

Code

English

apadenoson [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29707