CGS-21680

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H29N7O6
Molecular Weight	499.5197
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=C(NCCC4=CC=C(CCC(O)=O)C=C4)N=C3N

InChI

InChIKey=PAOANWZGLPPROA-RQXXJAGISA-N

InChI=1S/C23H29N7O6/c1-2-25-21(35)18-16(33)17(34)22(36-18)30-11-27-15-19(24)28-23(29-20(15)30)26-10-9-13-5-3-12(4-6-13)7-8-14(31)32/h3-6,11,16-18,22,33-34H,2,7-10H2,1H3,(H,25,35)(H,31,32)(H3,24,26,28,29)/t16-,17+,18-,22+/m0/s1

HIDE SMILES / InChI

Description

CGS -21680 is an adenosine A2 receptor agonist with IC50 of 22 nM, exhibits 140-fold over A1 receptor. In an isolated perfused working rat heart model, CGS -21680 effectively increases coronary flow with an ED25 value of 1.8 nM. CGS-21680 binds adenosine A2 receptor with high affinity (Kd = 15.5 nM). Novartis originated CGS- 21680 in Switzerland and discontinued its development later.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A2a receptor 31	Agonist 2,752		18.47 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575	Primary		Preclinical	Unknown
Myocardial ischemia 14	Primary		Preclinical	Unknown

PubMed

Show entries

Title	Date	PubMed
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.	1995 Jun 9	7775460
Mechanism and pressor relevance of the short-term cardiovascular and renin excitatory actions of the selective A2A-adenosine receptor agonists.	1997 Sep	9300315
Distinct protein kinase C isoforms mediate regulation of vascular endothelial growth factor expression by A2A adenosine receptor activation and phorbol esters in pheochromocytoma PC12 cells.	2003 Apr 25	12590138
Neuroprotective effect of L-DOPA co-administered with the adenosine A2A receptor agonist CGS 21680 in an animal model of Parkinson's disease.	2004 Aug 30	15342103
Synthesis and biological activity of new potential agonists for the human adenosine A2A receptor.	2004 Jul 29	15267242

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Patents

Sample Use Guides

In Vivo Use Guide

CGS-21680 is active p.o. in the spontaneously hypertensive rat at a dose of 10 mg/kg with efficacy for up to 24 hr.

Route of Administration: Oral

In Vitro Use Guide

CGS-21680 (100 nM) inhibited non-inactivating K+ current (IAC) by 78.4 +/- 4.6 % in bovine adrenal cortical cells.

Show entries

Name

Type

Language

2-(4-(2-CARBOXYETHYL)PHENETHYLAMINO)-5'-N- ETHYLCARBOXAMIDOADENOSINE

Preferred Name

English

CGS-21680

Common Name

English

BENZENEPROPANOIC ACID, 4-(2-((6-AMINO-9-(N-ETHYL-.BETA.-D-RIBOFURANURONAMIDOSYL)-9H-PURIN-2-YL)AMINO)ETHYL)-

Systematic Name

English

Showing 1 to 3 of 3 entries

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Code System

Code

Type

Description

PUBCHEM

3086599

PRIMARY

FDA UNII

T5HB1E831H

PRIMARY

WIKIPEDIA

CGS-21680

PRIMARY

EPA CompTox

DTXSID6043882

PRIMARY

CAS

120225-54-9

PRIMARY

Showing 1 to 5 of 5 entries

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ACTIVE MOIETY


					T5HB1E831H

CGS-21680