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Identification
- Generic Name
- Piclidenoson
- DrugBank Accession Number
- DB05511
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Piclidenoson (DB05511)
- Weight
- Average: 510.2857
Monoisotopic: 510.051246546 - Chemical Formula
- C18H19IN6O4
- Synonyms
- Piclidenoson
- External IDs
- CF-101
- CF101
- IB-MECA
Pharmacology
- Indication
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.
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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.
- Mechanism of action
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.
Target Actions Organism AAdenosine receptor A3 agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Purine nucleosides
- Sub Class
- Not Available
- Direct Parent
- Purine nucleosides
- Alternative Parents
- 6-alkylaminopurines / Glycosylamines / Benzylamines / Secondary alkylarylamines / Aminopyrimidines and derivatives / Iodobenzenes / Aryl iodides / Imidolactams / N-substituted imidazoles / Tetrahydrofurans show 10 more
- Substituents
- 1,2-diol / 6-alkylaminopurine / 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl halide / Aryl iodide / Azacycle show 34 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organoiodine compound, monocarboxylic acid amide, adenosines (CHEBI:73286)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 30679UMI0N
- CAS number
- 152918-18-8
- InChI Key
- HUJXGQILHAUCCV-MOROJQBDSA-N
- 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
- IUPAC Name
- (2S,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(3-iodophenyl)methyl]amino}-9H-purin-9-yl)-N-methyloxolane-2-carboxamide
- SMILES
- CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(NCC3=CC(I)=CC=C3)N=CN=C12
References
- General References
- Bar-Yehuda S, Silverman MH, Kerns WD, Ochaion A, Cohen S, Fishman P: The anti-inflammatory effect of A3 adenosine receptor agonists: a novel targeted therapy for rheumatoid arthritis. Expert Opin Investig Drugs. 2007 Oct;16(10):1601-13. [Article]
- External Links
- PubChem Compound
- 123683
- PubChem Substance
- 175427023
- ChemSpider
- 110259
- BindingDB
- 50118812
- ChEBI
- 73286
- ChEMBL
- CHEMBL119709
- ZINC
- ZINC000003811810
- PDBe Ligand
- Q8L
- PDB Entries
- 8cxw / 8d22 / 8x16
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Treatment Keratoconjunctivitis Sicca (KCS) 1 somestatus stop reason just information to hide 3 Completed Treatment Psoriasis Vulgaris (Plaque Psoriasis) 1 somestatus stop reason just information to hide 3 Terminated Treatment Rheumatoid Arthritis 1 somestatus stop reason just information to hide 2 Completed Prevention Rheumatoid Arthritis 1 somestatus stop reason just information to hide 2 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / Infections, Coronavirus 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.192 mg/mL ALOGPS logP 1 ALOGPS logP 0.6 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 12.39 Chemaxon pKa (Strongest Basic) 3.72 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 134.42 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 113.25 m3·mol-1 Chemaxon Polarizability 44.93 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8965 Blood Brain Barrier - 0.5807 Caco-2 permeable - 0.6658 P-glycoprotein substrate Substrate 0.5339 P-glycoprotein inhibitor I Non-inhibitor 0.8687 P-glycoprotein inhibitor II Inhibitor 0.5846 Renal organic cation transporter Non-inhibitor 0.9108 CYP450 2C9 substrate Non-substrate 0.7615 CYP450 2D6 substrate Non-substrate 0.835 CYP450 3A4 substrate Substrate 0.5348 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9072 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7671 Ames test Non AMES toxic 0.7609 Carcinogenicity Non-carcinogens 0.8473 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6008 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9801 hERG inhibition (predictor II) Non-inhibitor 0.5685
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.28804 predictedDeepCCS 1.0 (2019) [M+H]+ 193.68361 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.59613 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase (PubMed:8234299)
- Specific Function
- G protein-coupled adenosine receptor activity
- Gene Name
- ADORA3
- Uniprot ID
- P0DMS8
- Uniprot Name
- Adenosine receptor A3
- Molecular Weight
- 36184.175 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at November 18, 2007 18:25 / Updated at August 26, 2024 19:23