Piclidenoson

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
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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Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

TargetActionsOrganism
UAdenosine receptor A3Not AvailableHumans
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
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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
  1. 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]
PubChem Compound
123683
PubChem Substance
175427023
ChemSpider
110259
BindingDB
50118812
ChEBI
73286
ChEMBL
CHEMBL119709
ZINC
ZINC000003811810
PDBe Ligand
Q8L
PDB Entries
8cxw / 8d22

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentKeratoconjunctivitis Sicca (KCS)1
3CompletedTreatmentPsoriasis Vulgaris (Plaque Psoriasis)1
3TerminatedTreatmentRheumatoid Arthritis1
2CompletedPreventionRheumatoid Arthritis1
2CompletedTreatmentCoronavirus Disease 2019 (COVID‑19) / Infections, Coronavirus1

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
PropertyValueSource
Water Solubility0.192 mg/mLALOGPS
logP1ALOGPS
logP0.6Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.39Chemaxon
pKa (Strongest Basic)3.72Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area134.42 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity113.25 m3·mol-1Chemaxon
Polarizability44.93 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8965
Blood Brain Barrier-0.5807
Caco-2 permeable-0.6658
P-glycoprotein substrateSubstrate0.5339
P-glycoprotein inhibitor INon-inhibitor0.8687
P-glycoprotein inhibitor IIInhibitor0.5846
Renal organic cation transporterNon-inhibitor0.9108
CYP450 2C9 substrateNon-substrate0.7615
CYP450 2D6 substrateNon-substrate0.835
CYP450 3A4 substrateSubstrate0.5348
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9072
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7671
Ames testNon AMES toxic0.7609
CarcinogenicityNon-carcinogens0.8473
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6008 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9801
hERG inhibition (predictor II)Non-inhibitor0.5685
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uxr-2489100000-ca8ba69b00dc87548630
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0101190000-8c9db370b68554b941da
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000t-1109800000-f8731e8959f6d0a0554a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00mk-2938210000-083990a498b9d9300184
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w29-3309360000-97302a1e345d5a085fdc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ik9-2049410000-e3f1362d0294f26fe25b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0901000000-55933d1e6bd2bbc8022c
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-191.28804
predicted
DeepCCS 1.0 (2019)
[M+H]+193.68361
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.59613
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Adenosine receptor A3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
G-protein coupled adenosine receptor activity
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase. Possible role in reproduction.
Gene Name
ADORA3
Uniprot ID
P0DMS8
Uniprot Name
Adenosine receptor A3
Molecular Weight
36184.175 Da

Drug created at November 18, 2007 18:25 / Updated at February 21, 2021 18:51