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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 of 2-CHLOROADENOSINE

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

Molecular Formula C10H12ClN5O4
Molecular Weight 301.686
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
300.0 nM [Ki]
80.0 nM [Ki]
1.9 µM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
Effects of aminophylline and 2-chloroadenosine on seizures produced by pilocarpine in rats: morphological and electroencephalographic correlates.
1985 Dec 30
Potent convulsant actions of the adenosine receptor antagonist, xanthine amine congener (XAC).
1989
Structure-activity relationships for 2-substituted adenosines at A1 and A2 adenosine receptors.
1993
A binding site model and structure-activity relationships for the rat A3 adenosine receptor.
1994 Jun
Adenosine A2 receptors modulate haloperidol-induced catalepsy in rats.
1997 Jun 11
Identification of the adenine binding site of the human A1 adenosine receptor.
1999 Feb 5
Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors.
1999 Jan 1
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
Anticonvulsant effect and neurotransmitter modulation of focal and systemic 2-chloroadenosine against the development of pilocarpine-induced seizures.
2000 Sep
Effects of neuroprotective cocktails on hippocampal neuron death in an in vitro model of cerebral ischemia.
2001 Jan
Deaza- and deoxyadenosine derivatives: synthesis and inhibition of animal viruses as human infection models.
2003 May-Aug
[nhibitory effect of adenosine analogues on invasion of human ovarian cancer cell line HO-8910PM].
2004 Dec
Inhibition of phenylephrine-induced cardiomyocyte hypertrophy by activation of multiple adenosine receptor subtypes.
2005 Jan
Subtype-specific regulation of equilibrative nucleoside transporters by protein kinase CK2.
2005 Mar 1
Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:45:10 GMT 2023
Edited
by admin
on Fri Dec 15 18:45:10 GMT 2023
Record UNII
7W7ZUG45G8
Record Status Validated (UNII)
Record Version
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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
Created by admin on Fri Dec 15 18:45:10 GMT 2023 , Edited by admin on Fri Dec 15 18:45:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-678-3
Created by admin on Fri Dec 15 18:45:10 GMT 2023 , Edited by admin on Fri Dec 15 18:45:10 GMT 2023
PRIMARY
FDA UNII
7W7ZUG45G8
Created by admin on Fri Dec 15 18:45:10 GMT 2023 , Edited by admin on Fri Dec 15 18:45:10 GMT 2023
PRIMARY
MESH
D015762
Created by admin on Fri Dec 15 18:45:10 GMT 2023 , Edited by admin on Fri Dec 15 18:45:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID301017134
Created by admin on Fri Dec 15 18:45:10 GMT 2023 , Edited by admin on Fri Dec 15 18:45:10 GMT 2023
PRIMARY
NSC
36896
Created by admin on Fri Dec 15 18:45:10 GMT 2023 , Edited by admin on Fri Dec 15 18:45:10 GMT 2023
PRIMARY
PUBCHEM
8974
Created by admin on Fri Dec 15 18:45:10 GMT 2023 , Edited by admin on Fri Dec 15 18:45:10 GMT 2023
PRIMARY
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