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=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC(Cl)=N1

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 50 Target ID: CHEMBL318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8735640	Agonist 2678	300.0 nM [Ki]
Adenosine A2a receptor 30 Target ID: CHEMBL302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8735640	Agonist 2678	80.0 nM [Ki]
Adenosine A3 receptor 24 Target ID: CHEMBL3360 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8735640	Agonist 2678	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
		252159936
Effects of aminophylline and 2-chloroadenosine on seizures produced by pilocarpine in rats: morphological and electroencephalographic correlates.	1985 Dec 30	3936592
Potent convulsant actions of the adenosine receptor antagonist, xanthine amine congener (XAC).	1989	2779359
Hemodynamic effects of adenosine agonists in the conscious spontaneously hypertensive rat.	1990 Sep	2203898
Structure-activity relationships for 2-substituted adenosines at A1 and A2 adenosine receptors.	1993	8441759
Species difference in the G protein selectivity of the human and bovine A1-adenosine receptor.	1994 Dec 23	7798201
A binding site model and structure-activity relationships for the rat A3 adenosine receptor.	1994 Jun	8022403
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.	1995 Jun 9	7775460
Adenosine A2 receptors modulate haloperidol-induced catalepsy in rats.	1997 Jun 11	9218695
Identification of the adenine binding site of the human A1 adenosine receptor.	1999 Feb 5	9920910
Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors.	1999 Jan 1	9920286
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 Oct	10496952
Anticonvulsant effect and neurotransmitter modulation of focal and systemic 2-chloroadenosine against the development of pilocarpine-induced seizures.	2000 Sep	10974326
Effects of neuroprotective cocktails on hippocampal neuron death in an in vitro model of cerebral ischemia.	2001 Jan	11145473
Deaza- and deoxyadenosine derivatives: synthesis and inhibition of animal viruses as human infection models.	2003 May-Aug	14565301
[nhibitory effect of adenosine analogues on invasion of human ovarian cancer cell line HO-8910PM].	2004 Dec	15601553
Inhibition of phenylephrine-induced cardiomyocyte hypertrophy by activation of multiple adenosine receptor subtypes.	2005 Jan	15452191
Subtype-specific regulation of equilibrative nucleoside transporters by protein kinase CK2.	2005 Mar 1	15500446
Endogenous adenosine selectively modulates oxidant stress via the A1 receptor in ischemic hearts.	2009 Nov	19552606

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

Code

English

ADENOSINE, 2-CHLORO-

Systematic Name

English

Code System Code Type Description

CAS

146-77-0