Details of the Drug

General Information of Drug (ID: DM9G5XD)

Drug Name
IB-MECA
Synonyms
IB-Meca; 152918-18-8; piclidenoson; CF-101; 3-IB-Meca; N(6)-Ibamu; CF 101; Cf101; N(6)-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine; UNII-30679UMI0N; N(6)-(3-Iodobenzyl)adenosine-5'-N-methyluronamide; 1-Deoxy-1-(6-(((3-iodophenyl)methyl)amino)-9H-purin-9-yl)-N-methyl-beta-D-ribofuranuronamide; CHEMBL119709; CHEBI:73286; 30679UMI0N; RPR-113090; 3-iodobenzyl-5'-N-methylcarboxamidoadenosine; N(6)-(3-iodo-benzyl)adenosine-5'-N-methyluronamide; 3-IB-MECA
Indication
Disease Entry ICD 11 Status REF
Psoriasis vulgaris EA90 Phase 3 [1]
Solid tumour/cancer 2A00-2F9Z Phase 3 [2], [3], [4]
Plaque psoriasis EA90.0 Phase 2/3 [5]
Rheumatoid arthritis FA20 Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 510.3
Topological Polar Surface Area (xlogp) 0.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C18H19IN6O4
IUPAC Name
(2S,3S,4R,5R)-3,4-dihydroxy-5-[6-[(3-iodophenyl)methylamino]purin-9-yl]-N-methyloxolane-2-carboxamide
Canonical SMILES
CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=CC=C4)I)O)O
InChI
InChI=1S/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1
InChIKey
HUJXGQILHAUCCV-MOROJQBDSA-N
Cross-matching ID
PubChem CID
123683
ChEBI ID
CHEBI:73286
CAS Number
152918-18-8
DrugBank ID
DB05511
TTD ID
D0Y6ZK

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adenosine A3 receptor (ADORA3) TTJFY5U AA3R_HUMAN Agonist [6], [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 422).
3 Methotrexate enhances the anti-inflammatory effect of CF101 via up-regulation of the A3 adenosine receptor expression. Arthritis Res Ther. 2006;8(6):R169.
4 CF101, an agonist to the A3 adenosine receptor, enhances the chemotherapeutic effect of 5-fluorouracil in a colon carcinoma murine model. Neoplasia. 2005 Jan;7(1):85-90.
5 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
6 A role for central A3-adenosine receptors. Mediation of behavioral depressant effects. FEBS Lett. 1993 Dec 20;336(1):57-60.
7 A3 adenosine receptor as a target for cancer therapy. Anticancer Drugs. 2002 Jun;13(5):437-43.
8 2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists. Bioorg Med Chem. 2010 Mar 15;18(6):2195-2203.
9 Spiroindolones, a potent compound class for the treatment of malaria. Science. 2010 Sep 3;329(5996):1175-80.
10 2011 Pipeline of Can-Fite BioPharm.
11 Synthesis and evaluation of 1,2,4-triazolo[1,5-c]pyrimidine derivatives as A2A receptor-selective antagonists. Bioorg Med Chem Lett. 2010 Oct 1;20(19):5690-4.
12 2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacolog... J Med Chem. 2005 Nov 3;48(22):6887-96.
13 Protein kinase C protects preconditioned rabbit hearts by increasing sensitivity of adenosine A2b-dependent signaling during early reperfusion. J Mol Cell Cardiol. 2007 Sep;43(3):262-71.
14 Novel amino acid derived natural products from the ascidian Atriolum robustum: identification and pharmacological characterization of a unique aden... J Med Chem. 2004 Apr 22;47(9):2243-55.