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
Prenatal caffeine exposure induced a lower level of fetal blood leptin mainly via placental mechanism.	2015-11-15	26367767
Adenosine A2A receptor and TNF-α regulate the circadian machinery of the human monocytic THP-1 cells.	2013-02	22923002
A novel fused 1,2,4-triazine aryl derivative as antioxidant and nonselective antagonist of adenosine A(2A) receptors in ethanol-activated liver stellate cells.	2012-01-05	22063920
Adenosine reduces cell surface expression of toll-like receptor 4 and inflammation in response to lipopolysaccharide and matrix products.	2011-12	21538184
Adenosine up-regulates vascular endothelial growth factor in human macrophages.	2010-02-12	20067761
Compensatory upregulation of the adenosine system following phenylephrine-induced hypertrophy in cultured rat ventricular myocytes.	2010-02	19966059
Absence of adenosine-mediated aortic relaxation in A(2A) adenosine receptor knockout mice.	2009-11	19749167
Atheroprotective effects of methotrexate on reverse cholesterol transport proteins and foam cell transformation in human THP-1 monocyte/macrophages.	2008-12	19035488
Adenosine receptor agonists attenuate the development of diazepam withdrawal-induced sensitization in mice.	2008-06-24	18466897
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.	2008-01	17934014
Pharmacological characterization of a novel, potent adenosine A1 and A2A receptor dual antagonist, 5-[5-amino-3-(4-fluorophenyl)pyrazin-2-yl]-1-isopropylpyridine-2(1H)-one (ASP5854), in models of Parkinson's disease and cognition.	2007-11	17684118
Hyperalgesia, low-anxiety, and impairment of avoidance learning in neonatal caffeine-treated rats.	2007-03	17096081
Evidence for both adenosine A1 and A2A receptors activating single vagal sensory C-fibres in guinea pig lungs.	2006-09-01	16793905
Adenosine A(2A) receptors play a role in the pathogenesis of hepatic cirrhosis.	2006-08	16783407
Adenosine receptors as therapeutic targets.	2006-03	16518376
Influence of adenosine receptor agonists on benzodiazepine withdrawal signs in mice.	2005-10-31	16226742
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.	2005-10	16020631
Inhibition of phenylephrine-induced cardiomyocyte hypertrophy by activation of multiple adenosine receptor subtypes.	2005-01	15452191
Modulation of seizures and synaptic plasticity by adenosinergic receptors in an experimental model of temporal lobe epilepsy induced by pilocarpine in rats.	2005	15987273
2-Substituted adenosine derivatives: affinity and efficacy at four subtypes of human adenosine receptors.	2004-11-15	15476669
Neuroprotective effect of L-DOPA co-administered with the adenosine A2A receptor agonist CGS 21680 in an animal model of Parkinson's disease.	2004-08-30	15342103
Synthesis and biological activity of new potential agonists for the human adenosine A2A receptor.	2004-07-29	15267242
Participation of adenosine system in the ketamine-induced motor activity in mice.	2004-05-10	15849377
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.	2003-04-25	12590138
Cocaine-induced hyperactivity is more influenced by adenosine receptor agonists than amphetamine-induced hyperactivity.	2003-01-14	12523489
Impaired D2 dopamine receptor function in mice lacking type 5 adenylyl cyclase.	2002-09-15	12223546
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.	2001-02-13	11172060
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.	2000-12	11093773
[(3)H]MRE 3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A(3) adenosine receptors.	2000-05	10779381
Actions of adenosine A2A receptor antagonist KW-6002 on drug-induced catalepsy and hypokinesia caused by reserpine or MPTP.	1999-11	10591873
Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells.	1999-10	10496952
Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors.	1999-01-01	9920286
Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells.	1998-01	9459566
Mechanism and pressor relevance of the short-term cardiovascular and renin excitatory actions of the selective A2A-adenosine receptor agonists.	1997-09	9300315
Evidence against a major role of adenosine in oxygen-dependent regulation of erythropoietin in rats.	1997-08	9263988
Adenosine A2 receptors modulate haloperidol-induced catalepsy in rats.	1997-06-11	9218695
Characterization of human A2A adenosine receptors with the antagonist radioligand [3H]-SCH 58261.	1997-06	9179373
Neonatal capsaicin attenuates mechanical nociception in the rat.	1996-02-23	8907337
Selective adenosine A2A receptor/dopamine D2 receptor interactions in animal models of schizophrenia.	1996-01-11	8720578
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.	1995-06-09	7775460
KF17837: a novel selective adenosine A2A receptor antagonist with anticataleptic activity.	1994-05-02	8045270
Binding of the adenosine A2 receptor ligand [3H]CGS 21680 to human and rat brain: evidence for multiple affinity sites.	1990-11	2213023
[3H]CGS 21680, a selective A2 adenosine receptor agonist directly labels A2 receptors in rat brain.	1989-12	2600819

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

Download

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