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

Structure Search

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

Molecular Formula	C23H29N7O6
Molecular Weight	499.5197
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2795469 | https://www.ncbi.nlm.nih.gov/pubmed/2600819
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800000147

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 Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25780876 \| https://www.ncbi.nlm.nih.gov/pubmed/25221664 \| https://www.ncbi.nlm.nih.gov/pubmed/2795469	Agonist 2752		18.47 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://adisinsight.springer.com/drugs/800000147 https://www.ncbi.nlm.nih.gov/pubmed/11877342	Primary		Preclinical	Unknown Approved Use Unknown
Myocardial ischemia 14 Sources: http://adisinsight.springer.com/drugs/800000147 https://www.ncbi.nlm.nih.gov/pubmed/21044214 https://www.ncbi.nlm.nih.gov/pubmed/20709859 https://www.ncbi.nlm.nih.gov/pubmed/15821439	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Why are A(2B) receptors low-affinity adenosine receptors? Mutation of Asn273 to Tyr increases affinity of human A(2B) receptor for 2-(1-Hexynyl)adenosine.	2000 Dec	11093773
The role of the D(2) dopamine receptor (D(2)R) in A(2A) adenosine receptor (A(2A)R)-mediated behavioral and cellular responses as revealed by A(2A) and D(2) receptor knockout mice.	2001 Feb 13	11172060
Modulation of seizures and synaptic plasticity by adenosinergic receptors in an experimental model of temporal lobe epilepsy induced by pilocarpine in rats.	2005	15987273
Inhibition of phenylephrine-induced cardiomyocyte hypertrophy by activation of multiple adenosine receptor subtypes.	2005 Jan	15452191
Participation of adenosine system in the ketamine-induced motor activity in mice.	2005 Jan-Feb	15849377
A novel A1 adenosine receptor antagonist, L-97-1 [3-[2-(4-aminophenyl)-ethyl]-8-benzyl-7-{2-ethyl-(2-hydroxy-ethyl)-amino]-ethyl}-1-propyl-3,7-dihydro-purine-2,6-dione], reduces allergic responses to house dust mite in an allergic rabbit model of asthma.	2005 Oct	16020631
Influence of adenosine receptor agonists on benzodiazepine withdrawal signs in mice.	2005 Oct 31	16226742
Brainstem phosphorylated extracellular signal-regulated kinase 1/2-nitric-oxide synthase signaling mediates the adenosine A2A-dependent hypotensive action of clonidine in conscious aortic barodenervated rats.	2008 Jan	17934014

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:07:47 GMT 2025` Edited by `admin` on `Mon Mar 31 19:07:47 GMT 2025`
Record UNII	T5HB1E831H
Record Status	`Validated (UNII)`
Record Version

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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

Code System Code Type Description

PUBCHEM

3086599