CF-102 | Namodenoson | CAS#163042-96-4 | A3AR agonist

Namodenoson
new

featured

WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 206154

CAS#: 163042-96-4

Description: Namodenoson, also known as 2-Cl-IB-MECA and CF-102, is an orally bioavailable, synthetic, highly selective adenosine A3 receptor (A3AR) agonist with potential antineoplastic activity. Adenosine A3 receptor agonist CF102 selectively binds to and activates the cell surface-expressed A3AR, deregulating Wnt and NF-kB signal transduction pathways downstream, which may result in apoptosis of A3AR-expressing tumor cells. A3AR, a G protein-coupled receptor, is highly expressed on the cell surfaces of various solid tumor cell types, including hepatocellular carcinoma (HCC) cells, and plays an important role in cellular proliferation.

Chemical Structure

Namodenoson

CAS# 163042-96-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 206154
Name: Namodenoson
CAS#: 163042-96-4
Chemical Formula: C18H18ClIN6O4
Exact Mass: 544.01
Molecular Weight: 544.731
Elemental Analysis: C, 39.69; H, 3.33; Cl, 6.51; I, 23.30; N, 15.43; O, 11.75

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 1250
200mg	USD 1950
500mg	USD 3650
1g	USD 4250
2g	USD 6950
5g	USD 12550
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: CF102; CF-102; CF 102; Cl-IB-MECA; 2-Cl-IB-MECA; Namodenoson; Chloro-IB-MECA;

IUPAC/Chemical Name: (2S,3S,4R,5R)-5-(2-chloro-6-((3-iodobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxy-N-methyltetrahydrofuran-2-carboxamide

InChi Key: IPSYPUKKXMNCNQ-PFHKOEEOSA-N

InChi Code: InChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1

SMILES Code: O[C@H]1[C@H](N2C=NC3=C(NCC4=CC=CC(I)=C4)N=C(Cl)N=C23)O[C@H](C(NC)=O)[C@H]1O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Namodenoson (CF-102) is a selective A3 adenosine receptor (A3AR) agonist (Ki=0.33 nM).
In vitro activity:	CF102 at a concentration of 1 and 10 nM induced a linear inhibitory effect on the proliferation of Hep-3B cells (34.5 ± 2.5% and 46.87 ± 3.72%, respectively; Fig. 6). WB analysis showed that Hep-3B cells highly express A3AR which was down-regulated upon CF102 treatment (Fig. 7). Down-regulation of PI3K, PKB/Akt, and NF-κB was also found upon CF102 treatment whereas up-regulation of the pro-apoptotic protein caspase-3 was noted (Fig. 8). Reference: J Cell Physiol. 2011 Sep;226(9):2438-47. https://pubmed.ncbi.nlm.nih.gov/21660967/
In vivo activity:	The hemodynamic effects of the novel, selective adenosine A3 receptor agonist 2-chloro-N6-(3-iodobenzyl)adenosine-5'-N-methylcarboxamide (2-Cl-IB-MECA) were investigated in conscious rats. Intravenous administration of 200 micrograms/kg 2-Cl-IB-MECA resulted in a short-lasting hypotension, which was accompanied by a 50-100-fold increase in plasma histamine concentrations. Reference: Eur J Pharmacol. 1996 Jul 25;308(3):311-4. https://pubmed.ncbi.nlm.nih.gov/8858305/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	10.0	18.36
	DMSO	48.7	89.34
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.55

Preparing Stock Solutions

The following data is based on the product molecular weight 544.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Lillo A, Serrano-Marín J, Lillo J, Raïch I, Navarro G, Franco R. Gene regulation in activated microglia by adenosine A3 receptor agonists: a transcriptomics study. Purinergic Signal. 2023 Jan 27. doi: 10.1007/s11302-022-09916-9. Epub ahead of print. PMID: 36703008. 2. Cohen S, Stemmer SM, Zozulya G, Ochaion A, Patoka R, Barer F, Bar-Yehuda S, Rath-Wolfson L, Jacobson KA, Fishman P. CF102 an A3 adenosine receptor agonist mediates anti-tumor and anti-inflammatory effects in the liver. J Cell Physiol. 2011 Sep;226(9):2438-47. doi: 10.1002/jcp.22593. PMID: 21660967; PMCID: PMC3474360. 3. Ohana G, Cohen S, Rath-Wolfson L, Fishman P. A3 adenosine receptor agonist, CF102, protects against hepatic ischemia/reperfusion injury following partial hepatectomy. Mol Med Rep. 2016 Nov;14(5):4335-4341. doi: 10.3892/mmr.2016.5746. Epub 2016 Sep 19. PMID: 27666664. 4. Van Schaick EA, Jacobson KA, Kim HO, IJzerman AP, Danhof M. 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. doi: 10.1016/0014-2999(96)00373-1. PMID: 8858305; PMCID: PMC4287249.
In vitro protocol:	1. Lillo A, Serrano-Marín J, Lillo J, Raïch I, Navarro G, Franco R. Gene regulation in activated microglia by adenosine A3 receptor agonists: a transcriptomics study. Purinergic Signal. 2023 Jan 27. doi: 10.1007/s11302-022-09916-9. Epub ahead of print. PMID: 36703008. 2. Cohen S, Stemmer SM, Zozulya G, Ochaion A, Patoka R, Barer F, Bar-Yehuda S, Rath-Wolfson L, Jacobson KA, Fishman P. CF102 an A3 adenosine receptor agonist mediates anti-tumor and anti-inflammatory effects in the liver. J Cell Physiol. 2011 Sep;226(9):2438-47. doi: 10.1002/jcp.22593. PMID: 21660967; PMCID: PMC3474360.
In vivo protocol:	1. Ohana G, Cohen S, Rath-Wolfson L, Fishman P. A3 adenosine receptor agonist, CF102, protects against hepatic ischemia/reperfusion injury following partial hepatectomy. Mol Med Rep. 2016 Nov;14(5):4335-4341. doi: 10.3892/mmr.2016.5746. Epub 2016 Sep 19. PMID: 27666664. 2. Van Schaick EA, Jacobson KA, Kim HO, IJzerman AP, Danhof M. 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. doi: 10.1016/0014-2999(96)00373-1. PMID: 8858305; PMCID: PMC4287249.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

1: Soares AS, Costa VM, Diniz C, Fresco P. The combination of Cl-IB-MECA with paclitaxel: a new anti-metastatic therapeutic strategy for melanoma. Cancer Chemother Pharmacol. 2014 Oct;74(4):847-60. doi: 10.1007/s00280-014-2557-y. Epub 2014 Aug 14. PubMed PMID: 25119183.

2: Soares AS, Costa VM, Diniz C, Fresco P. Potentiation of cytotoxicity of paclitaxel in combination with Cl-IB-MECA in human C32 metastatic melanoma cells: A new possible therapeutic strategy for melanoma. Biomed Pharmacother. 2013 Oct;67(8):777-89. doi: 10.1016/j.biopha.2013.08.003. Epub 2013 Aug 23. PubMed PMID: 24035253.

3: Kim GD, Oh J, Jeong LS, Lee SK. Thio-Cl-IB-MECA, a novel A3 adenosine receptor agonist, suppresses angiogenesis by regulating PI3K/AKT/mTOR and ERK signaling in endothelial cells. Biochem Biophys Res Commun. 2013 Jul 19;437(1):79-86. doi: 10.1016/j.bbrc.2013.06.040. Epub 2013 Jun 21. PubMed PMID: 23791876.

4: Montinaro A, Forte G, Sorrentino R, Luciano A, Palma G, Arra C, Adcock IM, Pinto A, Morello S. Adoptive immunotherapy with Cl-IB-MECA-treated CD8+ T cells reduces melanoma growth in mice. PLoS One. 2012;7(9):e45401. doi: 10.1371/journal.pone.0045401. Epub 2012 Sep 24. PubMed PMID: 23028986; PubMed Central PMCID: PMC3454429.

5: Kim TH, Kim YK, Woo JS. The adenosine A3 receptor agonist Cl-IB-MECA induces cell death through Ca2⁺/ROS-dependent down regulation of ERK and Akt in A172 human glioma cells. Neurochem Res. 2012 Dec;37(12):2667-77. doi: 10.1007/s11064-012-0855-5. Epub 2012 Aug 10. PubMed PMID: 22878643.

6: Lee HS, Chung HJ, Lee HW, Jeong LS, Lee SK. Suppression of inflammation response by a novel A3 adenosine receptor agonist thio-Cl-IB-MECA through inhibition of Akt and NF-κB signaling. Immunobiology. 2011 Sep;216(9):997-1003. doi: 10.1016/j.imbio.2011.03.008. Epub 2011 Apr 7. PubMed PMID: 21514967.

7: Morello S, Sorrentino R, Montinaro A, Luciano A, Maiolino P, Ngkelo A, Arra C, Adcock IM, Pinto A. NK1.1 cells and CD8 T cells mediate the antitumor activity of Cl-IB-MECA in a mouse melanoma model. Neoplasia. 2011 Apr;13(4):365-73. PubMed PMID: 21472141; PubMed Central PMCID: PMC3071085.

8: Forte G, Sorrentino R, Montinaro A, Pinto A, Morello S. Cl-IB-MECA enhances TNF-α release in peritoneal macrophages stimulated with LPS. Cytokine. 2011 May;54(2):161-6. doi: 10.1016/j.cyto.2011.02.002. Epub 2011 Feb 26. PubMed PMID: 21354814.

9: Kim H, Kang JW, Lee S, Choi WJ, Jeong LS, Yang Y, Hong JT, Yoon do Y. A3 adenosine receptor antagonist, truncated Thio-Cl-IB-MECA, induces apoptosis in T24 human bladder cancer cells. Anticancer Res. 2010 Jul;30(7):2823-30. PubMed PMID: 20683018.

10: Morello S, Sorrentino R, Porta A, Forte G, Popolo A, Petrella A, Pinto A. Cl-IB-MECA enhances TRAIL-induced apoptosis via the modulation of NF-kappaB signalling pathway in thyroid cancer cells. J Cell Physiol. 2009 Nov;221(2):378-86. doi: 10.1002/jcp.21863. PubMed PMID: 19562684.

Your view history

Namodenoson new featured