piclidenoson   Click here for help

GtoPdb Ligand ID: 422

Abbreviated name: IB-MECA
Synonyms: CF 101 | CF101 | N(6)-ibamu
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Piclidenoson is a selective agonist of the adenosine A3 receptor. It has anti-inflammatory action which is being investigated for translation to the clinic [2].
Early investigations revealed anti-cancer effects [1,5,12].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 134.42
Molecular weight 510.05
XLogP 2.2
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNC(=O)C1OC(C(C1O)O)n1cnc2c1ncnc2NCc1cccc(c1)I
Isomeric SMILES CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1cccc(c1)I
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
InChI Key HUJXGQILHAUCCV-MOROJQBDSA-N
References
1. Bar-Yehuda S, Madi L, Silberman D, Gery S, Shkapenuk M, Fishman P. (2005)
CF101, an agonist to the A3 adenosine receptor, enhances the chemotherapeutic effect of 5-fluorouracil in a colon carcinoma murine model.
Neoplasia, 7 (1): 85-90. [PMID:15720820]
2. Borea PA, Gessi S, Bar-Yehuda S, Fishman P. (2009)
A3 adenosine receptor: pharmacology and role in disease.
Handb Exp Pharmacol, (193): 297-327. [PMID:19639286]
3. David M, Akerman L, Ziv M, Kadurina M, Gospodinov D, Pavlotsky F, Yankova R, Kouzeva V, Ramon M, Silverman MH et al.. (2012)
Treatment of plaque-type psoriasis with oral CF101: data from an exploratory randomized phase 2 clinical trial.
J Eur Acad Dermatol Venereol, 26 (3): 361-7. [PMID:21504485]
4. Feoktistov I, Garland EM, Goldstein AE, Zeng D, Belardinelli L, Wells JN, Biaggioni I. (2001)
Inhibition of human mast cell activation with the novel selective adenosine A(2B) receptor antagonist 3-isobutyl-8-pyrrolidinoxanthine (IPDX)(2).
Biochem. Pharmacol., 62 (9): 1163-73. [PMID:11705449]
5. Fishman P, Bar-Yehuda S, Ohana G, Barer F, Ochaion A, Erlanger A, Madi L. (2004)
An agonist to the A3 adenosine receptor inhibits colon carcinoma growth in mice via modulation of GSK-3 beta and NF-kappa B.
Oncogene, 23 (14): 2465-71. [PMID:14691449]
6. Fishman P, Cohen S, Bar-Yehuda S. (2013)
Targeting the A3 adenosine receptor for glaucoma treatment (review).
Mol Med Rep, 7 (6): 1723-5. [PMID:23563604]
7. Gallo-Rodriguez C, Ji XD, Melman N, Siegman BD, Sanders LH, Orlina J, Fischer B, Pu Q, Olah ME, van Galen PJ et al.. (1994)
Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.
J. Med. Chem., 37 (5): 636-46. [PMID:8126704]
8. Jacobson KA, Gao ZG. (2006)
Adenosine receptors as therapeutic targets.
Nat Rev Drug Discov, 5 (3): 247-64. [PMID:16518376]
9. Kim J, Wess J, van Rhee AM, Schöneberg T, Jacobson KA. (1995)
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.
J. Biol. Chem., 270 (23): 13987-97. [PMID:7775460]
10. Klotz KN, Hessling J, Hegler J, Owman C, Kull B, Fredholm BB, Lohse MJ. (1998)
Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells.
Naunyn Schmiedebergs Arch. Pharmacol., 357 (1): 1-9. [PMID:9459566]
11. Linden J, Thai T, Figler H, Jin X, Robeva AS. (1999)
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.
Mol. Pharmacol., 56 (4): 705-13. [PMID:10496952]
12. Ohana G, Bar-Yehuda S, Arich A, Madi L, Dreznick Z, Rath-Wolfson L, Silberman D, Slosman G, Fishman P. (2003)
Inhibition of primary colon carcinoma growth and liver metastasis by the A3 adenosine receptor agonist CF101.
Br. J. Cancer, 89 (8): 1552-8. [PMID:14562031]
13. Varani K, Merighi S, Gessi S, Klotz KN, Leung E, Baraldi PG, Cacciari B, Romagnoli R, Spalluto G, Borea PA. (2000)
[(3)H]MRE 3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A(3) adenosine receptors.
Mol. Pharmacol., 57 (5): 968-75. [PMID:10779381]
14. Varani K, Padovan M, Govoni M, Vincenzi F, Trotta F, Borea PA. (2010)
The role of adenosine receptors in rheumatoid arthritis.
Autoimmun Rev, 10 (2): 61-4. [PMID:20691813]