2-CL-IB-MECA

Names

[ Name ]:
2-CL-IB-MECA

[Synonym ]:
CF102
CI-IB-MECA
2-Cl-IB-Meca
Cl-IB-MECA
Namodenoson
2-chloro-IB-MECA
(2S,3S,4R,5R)-5-{2-Chloro-6-[(3-iodobenzyl)amino]-9H-purin-9-yl}-3,4-dihydroxy-N-methyltetrahydro-2-furancarboxamide (non-preferred name)
UNII:Z07JR07J6C
CF-102
CF-102(2-Cl-IB-MECA)

Biological Activity

[Description]:

Namodenoson (CF-102) is a selective A3 adenosine receptor agonist (Ki = 0.33 nM). Displays 2500- and 1400-fold selectivity over A1 and A2A receptors respectively.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adenosine Receptor

Research Areas >> Cancer

[Target]

Ki:0.33 nM (A3 adenosine receptor)[1][2].

[In Vitro]

In human ADF cells of astroglial lineage, 100 nM Namodenoson (2-Cl-IB-MECA) caused a marked reorganization of the cytoskeleton, with appearance of stress fibres and numerous cell protrusions. High concentrations of Namodenoson (2-Cl-IB-MECA) directly cause influx of Ca2+[2].

[In Vivo]

Intravenous administration of 200 μg/kg Namodenoson (2-Cl-IB-MECA) resulted in a short-lasting hypotension, which was accompanied by a 50-100-fold increase in plasma histamine concentrations. Administration of a second dose of Namodenoson (2-Cl-IB-MECA) did not elicit any hemodynamic effects[1].

[References]

[1]. Van Schaick EA et al. Hemodynamic effects and histamine release elicited by the selective adenosine A3 receptor agonist 2-Cl-IB-MECA in conscious rats. Eur J Pharmacol. 1996 Jul 25;308(3):311-4.

[2]. Jacobson KA et al. Adenosine A3 receptors: novel ligands and paradoxical effects. Trends Pharmacol Sci. 1998 May;19(5):184-91.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Melting Point ]:
209 °C

[ Molecular Formula ]:
C₁₈H₁₈ClIN₆O₄

[ Molecular Weight ]:
544.731

[ Exact Mass ]:
544.012268

[ PSA ]:
134.42000

[ LogP ]:
3.14

[ Index of Refraction ]:
1.814

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

The combination of Cl-IB-MECA with paclitaxel: a new anti-metastatic therapeutic strategy for melanoma.

Cancer Chemother. Pharmacol. 74(4) , 847-60, (2014)

Metastatic melanoma is considered one of the most aggressive malignant tumours, representing the deadliest form of skin cancer. Melanoma progression is associated with the abrogation of normal control...

Activation of hippocampal adenosine A3 receptors produces a desensitization of A1 receptor-mediated responses in rat hippocampus.

J. Neurosci. 17 , 607-614, (1997)

The adenosine A3 receptor is expressed in brain, but the consequences of activation of this receptor on electrophysiological activity are unknown. We have characterized the actions of a selective aden...

Modulation of A1 and A2B adenosine receptor activity: a new strategy to sensitise glioblastoma stem cells to chemotherapy.

Cell Death Dis. 5 , e1539, (2014)

Therapies that target the signal transduction and biological characteristics of cancer stem cells (CSCs) are innovative strategies that are used in combination with conventional chemotherapy and radio...