NAMODENOSON

Investigational

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

Molecular Formula	C18H18ClIN6O4
Molecular Weight	544.731
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 2752		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 1147	Unknown Approved Use Unknown
Nonalcoholic steatohepatitis 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02927314	Primary	Phase II 1147	Unknown Approved Use Unknown
Chronic hepatitis C 42 Sources: http://adisinsight.springer.com/drugs/800013700	Primary	Phase II 1147	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	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23299770	Sources: https://pubmed.ncbi.nlm.nih.gov/23299770

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
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
KeyOrganics	DS-16397	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-16397
mcule	MCULE-3865111822	https://mcule.com/MCULE-3865111822/
mcule	MCULE-9395587114	https://mcule.com/MCULE-9395587114/
MedChem Express	HY-12365	https://www.medchemexpress.com/search.html?q=HY-12365&ft=&fa=&fp=
Molcore	MC106191	http://www.molcore.com/CatMC106191.html
Molnova	M12449	https://www.molnova.com/en/serch-list.html?keywords=M12449
MolPort	MolPort-003-940-691	https://www.molport.com/shop/molecule-link/MolPort-003-940-691
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

PubMed

Title	Date	PubMed
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.	2013-10	23650147
Control of enteric neuromuscular functions by purinergic A(3) receptors in normal rat distal colon and experimental bowel inflammation.	2010-10	20860664
A(3) adenosine receptor activation during reperfusion reduces infarct size through actions on bone marrow-derived cells.	2010-08	20132822
Adenosine A1 and A3 receptors protect astrocytes from hypoxic damage.	2008-10-31	18727925
Short- and long-term A3 adenosine receptor activation inhibits the Na+/H+ exchanger NHE3 activity and expression in opossum kidney cells.	2008-07	18286509
Dual purinergic synaptic transmission in the human enteric nervous system.	2008-02	18079280
The role of adenosine A2A and A3 receptors on the differential modulation of norepinephrine and neuropeptide Y release from peripheral sympathetic nerve terminals.	2006-03	16539684
Adenosine receptors as therapeutic targets.	2006-03	16518376
Different roles of adenosine A1, A2A and A3 receptors in controlling kainate-induced toxicity in cortical cultured neurons.	2005-10	16011860
The role of adenosine A2A and A2B receptors in the regulation of TNF-alpha production by human monocytes.	2005-03-15	15748700
Functional expression of adenosine A2A and A3 receptors in the mouse dendritic cell line XS-106.	2003-08-01	12909194
p53-Independent induction of Fas and apoptosis in leukemic cells by an adenosine derivative, Cl-IB-MECA.	2002-03-01	11911839
Induction of apoptosis in rat cardiocytes by A3 adenosine receptor activation and its suppression by isoproterenol.	2000-05-25	10854059
Activation of the A3 adenosine receptor affects cell cycle progression and cell growth.	2000-03	10731034
Pharmacological characterization of novel A3 adenosine receptor-selective antagonists.	1997-09	9364471
2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.	1994-10-14	7932588

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:07:02 GMT 2025` Edited by `admin` on `Mon Mar 31 19:07:02 GMT 2025`
Record UNII	Z07JR07J6C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Preferred Name

English

NAMODENOSON

Official Name

English

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

Common Name

English

CF-102

Code

English

CF102

Code

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