NAMODENOSON

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H18ClIN6O4
Molecular Weight	544.731
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=C(Cl)N=C3NCC4=CC=CC(I)=C4

InChI

InChIKey=IPSYPUKKXMNCNQ-PFHKOEEOSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7932588 | https://www.ncbi.nlm.nih.gov/pubmed/26126429 | http://www.canfite.com/?KPageId=20

CF102 known as Cl-IB-MECA (2-chloro-N6-(3-iodobenzyl)-adenosine-5’- N-methyl-uronamide), is a highly specific and selective agonist at the A3 adenosine receptor. Phase I/II study in hepatocellular carcinoma (HCC) successfully met its primary and secondary endpoints demonstrating initial indications for efficacy of CF102. A global Phase II study treating patients with CF102 as a second line therapy will start enroling patients shortly.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A3 receptor 24 Target ID: CHEMBL256 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7932588 \| https://www.ncbi.nlm.nih.gov/pubmed/26126429 \| https://www.ncbi.nlm.nih.gov/pubmed/12754103	Agonist 2678		1.4 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Hepatocellular carcinoma 83 Sources: http://www.canfite.com/?KPageId=20 https://www.ncbi.nlm.nih.gov/pubmed/23299770	Primary	Phase II 1132	Unknown Approved Use Unknown
Nonalcoholic steatohepatitis 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02927314	Primary	Phase II 1132	Unknown Approved Use Unknown
Chronic hepatitis C 42 Sources: http://adisinsight.springer.com/drugs/800013700	Primary	Phase II 1132	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
25 mg 2 times / day multiple, oral Highest studied dose Dose: 25 mg, 2 times / day Route: oral Route: multiple Dose: 25 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23299770 Page: p.1	unhealthy, ADULT n = 6 Health Status: unhealthy Condition: hepatocellular carcinoma Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/23299770 Page: p.1	Sources: https://pubmed.ncbi.nlm.nih.gov/23299770 Page: p.1

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY106191	https://www.001chemical.com/chem/search?q=DY106191
1PlusChem LLC	1P001U3O	https://www.1pchem.com/search?query=1P001U3O
A2B Chem	AA84868	http://a2bchem.com/prod/AA84868
Ambeed	A138589	http://www.ambeed.com/search/Search.html?keyword=A138589
Angene	AGN-PC-0Q8C62	http://www.angenechemical.com/productshow/AGN-PC-0Q8C62.html
ApexBio Technology	B6597	https://www.apexbt.com/catalogsearch/result/?q=B6597
AstaTech	P10208	http://astatechinc.com/CPSResult.php?CRNO=P10208
BLD Pharm	BD55443	http://www.bldpharm.com/search/Search.html?keyword=BD55443
BOC Sciences	163042-96-4	http://www.bocsci.com/description.asp?cas=163042-96-4
Chem Scene	CS-5932	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5932
ChemShuttle	179928	https://www.chemshuttle.com/catalogsearch/result/?q=179928
Combi-Blocks	QM-6551	http://www.combi-blocks.com/cgi-bin/find.cgi?QM-6551
KeyOrganics	DS-16397	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-16397
MedChem Express	HY-12365	https://www.medchemexpress.com/search.html?q=HY-12365&ft=&fa=&fp=
MolPort	MolPort-003-940-691	https://www.molport.com/shop/molecule-link/MolPort-003-940-691
Molcore	MC106191	http://www.molcore.com/CatMC106191.html
Molnova	M12449	https://www.molnova.com/en/serch-list.html?keywords=M12449
MuseChem	I002116	https://www.musechem.com/product/I002116.html
Tetrahedron	TS73137	http://www.thsci.com/search.do?q=TS73137
Tocris	1104	https://www.tocris.com/search.php?Type=QuickSearch&Value=1104
Toronto Research Chemicals	C576230	https://www.trc-canada.com/product-detail/?CatNum=C576230
eMolecules	106286264	https://orderbb.emolecules.com/search/#?query=106286264
eMolecules	48877804	https://orderbb.emolecules.com/search/#?query=48877804
eMolecules	535938	https://orderbb.emolecules.com/search/#?query=535938
eNovation Chemicals	D574117	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D574117&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-3865111822	https://mcule.com/MCULE-3865111822/
mcule	MCULE-9395587114	https://mcule.com/MCULE-9395587114/

PubMed

Title	Date	PubMed
2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.	1994 Oct 14	7932588
Pharmacological characterization of novel A3 adenosine receptor-selective antagonists.	1997 Sep	9364471
Activation of the A3 adenosine receptor affects cell cycle progression and cell growth.	2000 Mar	10731034
Induction of apoptosis in rat cardiocytes by A3 adenosine receptor activation and its suppression by isoproterenol.	2000 May 25	10854059
p53-Independent induction of Fas and apoptosis in leukemic cells by an adenosine derivative, Cl-IB-MECA.	2002 Mar 1	11911839
Functional expression of adenosine A2A and A3 receptors in the mouse dendritic cell line XS-106.	2003 Aug 1	12909194
The role of adenosine A2A and A2B receptors in the regulation of TNF-alpha production by human monocytes.	2005 Mar 15	15748700
Different roles of adenosine A1, A2A and A3 receptors in controlling kainate-induced toxicity in cortical cultured neurons.	2005 Oct	16011860
The role of adenosine A2A and A3 receptors on the differential modulation of norepinephrine and neuropeptide Y release from peripheral sympathetic nerve terminals.	2006 Mar	16539684
Adenosine receptors as therapeutic targets.	2006 Mar	16518376
Dual purinergic synaptic transmission in the human enteric nervous system.	2008 Feb	18079280
Short- and long-term A3 adenosine receptor activation inhibits the Na+/H+ exchanger NHE3 activity and expression in opossum kidney cells.	2008 Jul	18286509
Adenosine A1 and A3 receptors protect astrocytes from hypoxic damage.	2008 Oct 31	18727925
A(3) adenosine receptor activation during reperfusion reduces infarct size through actions on bone marrow-derived cells.	2010 Aug	20132822
Control of enteric neuromuscular functions by purinergic A(3) receptors in normal rat distal colon and experimental bowel inflammation.	2010 Oct	20860664
Resveratrol 3-O-D-glucuronide and resveratrol 4'-O-D-glucuronide inhibit colon cancer cell growth: evidence for a role of A3 adenosine receptors, cyclin D1 depletion, and G1 cell cycle arrest.	2013 Oct	23650147

Patents

Sample Use Guides

In Vivo Use Guide

The primary objectives of a phase I/II, open-label, dose-escalation study were to examine the safety and pharmacokinetic behavior of CF102 given orally (1, 5, and 25 mg BID) in 28-day cycles.

Route of Administration: Oral

In Vitro Use Guide

CF102 at a concentration of 1 and 10 nM induced a linear inhibitory effect on the proliferation of Hep-3B cells

Name

Type

Language

NAMODENOSON

Official Name

English

2-CHLORO-N6-(3-IODOBENZYL)ADENOSINE-5'-N-METHYLURONAMIDE

Common Name

English

CF-102

Code

English

CF102

Code

English

2-CHLORO-N(6)-(3-IODOBENZYL)ADENOSINE-5'-N-METHYLURONAMIDE

Common Name

English

.BETA.-D-RIBOFURANURONAMIDE, 1-(2-CHLORO-6-(((3-IODOPHENYL)METHYL)AMINO)-9H-PURIN-9-YL)-1-DEOXY-N-METHYL-

Systematic Name

English

1-(2-CHLORO-6-(((3-IODOPHENYL)METHYL)AMINO)-9H-PURIN-9-YL)-1-DEOXY-N-METHYL-.BETA.-D-RIBOFURANURONAMIDE

Systematic Name

English

Namodenoson [WHO-DD]

Common Name

English

CHLORO-IB-MECA

Common Name

English

NAMODENOSON [USAN]

Common Name

English

namodenoson [INN]

Common Name

English

CL-IB-MECA

Code

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/15/1565