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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 of CGS-21680

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
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.

Originator

Curator's Comment: # Novartis

Approval Year

PubMed

PubMed

TitleDatePubMed
KF17837: a novel selective adenosine A2A receptor antagonist with anticataleptic activity.
1994 May 2
Neonatal capsaicin attenuates mechanical nociception in the rat.
1996 Feb 23
Mechanism and pressor relevance of the short-term cardiovascular and renin excitatory actions of the selective A2A-adenosine receptor agonists.
1997 Sep
[(3)H]MRE 3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A(3) adenosine receptors.
2000 May
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
Cocaine-induced hyperactivity is more influenced by adenosine receptor agonists than amphetamine-induced hyperactivity.
2002 Jul-Aug
Impaired D2 dopamine receptor function in mice lacking type 5 adenylyl cyclase.
2002 Sep 15
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
Inhibition of phenylephrine-induced cardiomyocyte hypertrophy by activation of multiple adenosine receptor subtypes.
2005 Jan
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
Atheroprotective effects of methotrexate on reverse cholesterol transport proteins and foam cell transformation in human THP-1 monocyte/macrophages.
2008 Dec
Compensatory upregulation of the adenosine system following phenylephrine-induced hypertrophy in cultured rat ventricular myocytes.
2010 Feb
Patents

Sample Use Guides

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
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 Fri Dec 15 18:11:53 GMT 2023
Edited
by admin
on Fri Dec 15 18:11:53 GMT 2023
Record UNII
T5HB1E831H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
2-(4-(2-CARBOXYETHYL)PHENETHYLAMINO)-5'-N- ETHYLCARBOXAMIDOADENOSINE
Common Name English
Code System Code Type Description
PUBCHEM
3086599
Created by admin on Fri Dec 15 18:11:53 GMT 2023 , Edited by admin on Fri Dec 15 18:11:53 GMT 2023
PRIMARY
FDA UNII
T5HB1E831H
Created by admin on Fri Dec 15 18:11:53 GMT 2023 , Edited by admin on Fri Dec 15 18:11:53 GMT 2023
PRIMARY
WIKIPEDIA
CGS-21680
Created by admin on Fri Dec 15 18:11:53 GMT 2023 , Edited by admin on Fri Dec 15 18:11:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID6043882
Created by admin on Fri Dec 15 18:11:53 GMT 2023 , Edited by admin on Fri Dec 15 18:11:53 GMT 2023
PRIMARY
CAS
120225-54-9
Created by admin on Fri Dec 15 18:11:53 GMT 2023 , Edited by admin on Fri Dec 15 18:11:53 GMT 2023
PRIMARY
Related Record Type Details
LABELED -> NON-LABELED
OFF TARGET->WEAK INHIBITOR
Binding Assay
IC50
TARGET -> AGONIST
BINDING
Kd
TARGET -> AGONIST
BINDING
IC50
Related Record Type Details
ACTIVE MOIETY