Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H19IN6O4 |
Molecular Weight | 510.2857 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C(NCC4=CC(I)=CC=C4)N=CN=C23
InChI
InChIKey=HUJXGQILHAUCCV-MOROJQBDSA-N
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
Piclidenoson (CF101), generically known as IB-MECA (methyl 1-[N6-(3-iodobenzyl)-adenin-9-yl]-b-D-ribofuronamide), is an oral small molecule drug formulated in a tablet. The activity of CF101 as an anti-inflammatory agent has been tested in a number of different experimental models including adjuvant and collagen induced arthritis and inflammatory bowel disease. CF101 is a highly specific agonist at the A3AR known to induce a robust anti-inflammatory effect in different experimental animal models. The CF101 mechanism of action entails down-regulation of the NF-κB-TNF-α signaling pathway, resulting in inhibition of pro-inflammatory cytokine production and apoptosis of inflammatory cells. Piclidenoson is currently being developed for the treatment of autoimmune inflammatory diseases like RA and psoriasis, hoping to replace the current standard of care, methotrexate (MTX). Can-Fite has tested CF101 in a number of Phase II studies in different diseases. A Phase II study in Psoriasis successfully met its primary endpoint showing that CF101 effectively ameliorated disease symptoms. In an interim analysis of the Phase II/III study the data justified full enrollment of the study. Phase II studies in Rheumatoid Arthritis (RA) demonstrated efficacy of CF101 given as a monotherapy. Moreover, a direct correlation between A3AR at baseline and patients’ response to CF101, suggesting its utilization as a predictive biomarker. Piclidenoson is headed into Phase 3 trials for RA and psoriasis.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
3.6 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://rheumatoidarthritisnews.com/2017/04/28/phase-3-trial-can-fites-piclidenoson-treatment-ra-rheumatoid-arthritis-underway/ http://adisinsight.springer.com/drugs/800015868 http://www.evaluategroup.com/Universal/View.aspx?type=Story&id=687189 https://www.ncbi.nlm.nih.gov/pubmed/26886128 |
Primary | Unknown Approved UseUnknown |
||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
2 mg 2 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
49 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
3 mg 2 times / day multiple, oral dose: 3 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
58.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
4 mg 2 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
79.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
242.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
2 mg 2 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
341.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
3 mg 2 times / day multiple, oral dose: 3 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
458.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
4 mg 2 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
601 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.83 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
2 mg 2 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
3 mg 2 times / day multiple, oral dose: 3 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
8.93 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
4 mg 2 times / day multiple, oral dose: 4 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15516022 |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PICLIDENOSON plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Inhibition of experimental auto-immune uveitis by the A3 adenosine receptor agonist CF101. | 2011 Nov |
|
Targeting the A3 adenosine receptor for glaucoma treatment (review). | 2013 Jun |
|
Treatment of Plaque-Type Psoriasis With Oral CF101: Data from a Phase II/III Multicenter, Randomized, Controlled Trial. | 2016 Aug 1 |
|
The A3 adenosine receptor (A3AR): therapeutic target and predictive biological marker in rheumatoid arthritis. | 2016 Sep |
Sample Use Guides
Treatment for rheumatoid arthritis: Piclidenoson will be given at 1 mg or 2 mg, twice daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10369472
C5a-induced EPO release in human eosinophils was inhibited dose-dependently by the selective A3 agonist Piclidenoson (IB-MECA). The IC50 (95% CI) for IB-MECA was 6.8 uM (3.1-12.0 uM). IB-MECA also significantly inhibited C5a-induced O2- release with IC50 (95% CI) of 9.5 uM (4.6-13.1 uM).
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ACTIVE MOIETY