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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8735640 |
300.0 nM [Ki] | ||
Target ID: CHEMBL302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8735640 |
80.0 nM [Ki] | ||
Target ID: CHEMBL3360 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8735640 |
1.9 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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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 |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2779359
Mice: 1 mg/kg, 20 minutes prior to xanthine amine congener or caffeine infusion
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4330088
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
Edited
Fri Dec 15 18:45:10 GMT 2023
by
admin
on
Fri Dec 15 18:45:10 GMT 2023
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Record UNII |
7W7ZUG45G8
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Record Status |
Validated (UNII)
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Record Version |
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