2-CHLOROADENOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12ClN5O4
Molecular Weight	301.686
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(Cl)=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

InChIKey=BIXYYZIIJIXVFW-UUOKFMHZSA-N

InChI=1S/C10H12ClN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9178649 | https://www.ncbi.nlm.nih.gov/pubmed/8735640 | https://www.ncbi.nlm.nih.gov/pubmed/13141221

2-chloroadenosine is a non-metabolizable adenosine receptors agonist. 2-chloroadenosine not only acts as an anticonvulsant against electrically induced kindled seizures, and against audiogenic seizures, electroshock and a variety of chemical convulsants, it prevents the development of the epileptic state by kindling-stimulation, i.e., it is antiepileptogenic. 2-chloroadenosine readily produce gastric erosions and ulcers in the rat. 2-Chloroadenosine produces pancreatitis, unique in that the lesions are mainly segmental in type. 2-chloroadenosine is known to be hypotensive substance.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adenosine A1 receptor 54 Target ID: CHEMBL318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8735640	Agonist 2752	300.0 nM [Ki]
Adenosine A2a receptor 31 Target ID: CHEMBL302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8735640	Agonist 2752	80.0 nM [Ki]
Adenosine A3 receptor 24 Target ID: CHEMBL3360 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8735640	Agonist 2752	1.9 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9439826 https://www.ncbi.nlm.nih.gov/pubmed/4043018 https://www.ncbi.nlm.nih.gov/pubmed/2779359 https://www.ncbi.nlm.nih.gov/pubmed/9178649	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Endogenous adenosine selectively modulates oxidant stress via the A1 receptor in ischemic hearts.	2009-11	19552606
Adenosine A3 receptor deficiency exerts unanticipated protective effects on the pressure-overloaded left ventricle.	2008-10-21	18838560
Long-term stimulation of adenosine A2b receptors begun after myocardial infarction prevents cardiac remodeling in rats.	2006-10-31	17043167
Subtype-specific regulation of equilibrative nucleoside transporters by protein kinase CK2.	2005-03-01	15500446
Inhibition of phenylephrine-induced cardiomyocyte hypertrophy by activation of multiple adenosine receptor subtypes.	2005-01	15452191
[nhibitory effect of adenosine analogues on invasion of human ovarian cancer cell line HO-8910PM].	2004-12	15601553
Deaza- and deoxyadenosine derivatives: synthesis and inhibition of animal viruses as human infection models.	2003-10-21	14565301
Adenine and deazaadenine nucleoside and deoxynucleoside analogues: inhibition of viral replication of sheep MVV (in vitro model for HIV) and bovine BHV-1.	2002-09	12110319
Effects of neuroprotective cocktails on hippocampal neuron death in an in vitro model of cerebral ischemia.	2001-01	11145473
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
Anticonvulsant effect and neurotransmitter modulation of focal and systemic 2-chloroadenosine against the development of pilocarpine-induced seizures.	2000-09	10974326
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
Identification of the adenine binding site of the human A1 adenosine receptor.	1999-02-05	9920910
Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors.	1999-01-01	9920286
Adenosine A2 receptors modulate haloperidol-induced catalepsy in rats.	1997-06-11	9218695
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.	1995-06-09	7775460
Species difference in the G protein selectivity of the human and bovine A1-adenosine receptor.	1994-12-23	7798201
A binding site model and structure-activity relationships for the rat A3 adenosine receptor.	1994-06	8022403
Structure-activity relationships for 2-substituted adenosines at A1 and A2 adenosine receptors.	1993	8441759
[Effects of agonists and antagonists of benzodiazepine, GABA and NMDA receptors, on caffeine-induced seizures in mice].	1992-08	1329401
Hemodynamic effects of adenosine agonists in the conscious spontaneously hypertensive rat.	1990-09	2203898
Potent convulsant actions of the adenosine receptor antagonist, xanthine amine congener (XAC).	1989	2779359
Effects of aminophylline and 2-chloroadenosine on seizures produced by pilocarpine in rats: morphological and electroencephalographic correlates.	1985-12-30	3936592
Adenosine receptor activation in human fibroblasts: nucleoside agonists and antagonists.	1980-06	6253037

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 1 mg/kg, 20 minutes prior to xanthine amine congener or caffeine infusion

Route of Administration: Intraperitoneal

In Vitro Use Guide

2-chloroadenosine caused partial inhibition of human platelet 3': 5'-cyclic AMP phosphodiesterase at 0.3 mM (11.7 % inhibition) and 3 (57.6%) mM.

Name

Type

Language

2-CHLOROADENOSINE

Systematic Name

English

NSC-36896

Preferred Name

English

ADENOSINE, 2-CHLORO-

Systematic Name

English

Code System Code Type Description

CAS

146-77-0