IB-MECA
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IB-MECA
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CAS No:
152918-18-8
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Formula:
C18H19IN6O4
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Chemical Name:
IB-MECA
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Synonyms:
β-D-Ribofuranuronamide,1-deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-;1-Deoxy-1-[6-[[(3-iodophenyl)methyl]amino]-9H-purin-9-yl]-N-methyl-β-D-ribofuranuronamide;N6-(3-Iodobenzyl)adenosine-5′-N-methyluronamide;IB-MECA;CF 101;Piclidenoson;215462-30-9
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CAS No:
Description
3-iodobenzyl-5'-N-methylcarboxamidoadenosine is a derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and one of the hydrogens of the exocyclic amino function is substituted by a 3-iodobenzyl group. It has a role as an adenosine A3 receptor agonist. It is a member of adenosines, an organoiodine compound and a monocarboxylic acid amide. It derives from an adenosine.|CF 101 (known generically as IB-MECA) is an anti-inflammatory drug for rheumatoid arthritis patients. Its novel mechanism of action relies on antagonism of adenoside A3 receptors. CF101 is supplied as an oral drug and has an excellent safety profile. It is also being considered for the treatment of other autoimmune-inflammatory disorders, such as Crohn's disease, psorasis and dry eye syndrome.|Piclidenoson is an orally bioavailable, adenosine A3 receptor (A3AR) agonist with potential anti-inflammatory activity. Upon administration, piclidenoson selectively targets, binds to and activates the cell surface-expressed A3AR, thereby activating transduction pathways in which A3AR plays a key role. This inhibits nuclear factor-kappa B (NF-kB) signaling and inhibits inflammatory cytokine production, such as tumor necrosis factor (TNF) and several interleukins. A3AR, a G protein-coupled receptor, plays a key role in many inflammatory diseases, and in certain types of cancer.
Drug Information
Investigated for use/treatment in cancer/tumors (unspecified), eye disorders/infections, psoriasis and psoriatic disorders, and rheumatoid arthritis. Can-Fite BioPharma has reported that by targeting the adenosine A3-receptor, CF101 may also be used to treat Crohn's disease, a serious gastrointestinal disorder.
CF-101 is an adenoside A3 agonist for the treatment of a variety of autoimmune-inflammatory disorders, particularly rhematoid arthritis. In clinical trials, it was found to be safe, well tolerated and showed strong evidence of an anti-inflammatory effect in rheumatoid arthritis patients. In this trial, a statistically significant correlation was found between A(3)AR expression level and response to the drug, so A(3)AR expression may serve as a biopredictor of patient response.
CF 101 is an A(3)AR agonist. A(3)AR is highly expressed in inflammatory cells and overexpressed in peripheral blood mononuclear cells, reflecting its role in the remote inflammatory process. In normal tissues, there is low adenoside A3 receptor expression. A(3)AR activation with a specific agonist deregulates the NF-kappaB signaling pathway in inflammatory cells and initiates immunomodulatory effects.
3-IB-MECA
Computed Properties
Molecular Weight:510.3
XLogP3:0.9
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:510.05125
Monoisotopic Mass:510.05125
Topological Polar Surface Area:134
Heavy Atom Count:29
Complexity:589
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
