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Merck
CN

I146

IB-MECA

solid, ≥98% (HPLC)

Synonym(s):

1-Deoxy-1-[6-[((3-Iodophenyl)methyl)amino]-9H-purin-9-yl]-N-methyl-β-D-ribofuranuronamide, N6-(3-Iodobenzyl)adenosine-5′-N-methyluronamide

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About This Item

Empirical Formula (Hill Notation):
C18H19IN6O4
CAS Number:
152918-18-8
Molecular Weight:
510.29
NACRES:
NA.32
PubChem Substance ID:
24277717
UNSPSC Code:
12352200
MDL number:
MFCD00671785

Key Documents

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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

SMILES string

CNC(=O)[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCc4cccc(I)c4)ncnc23

InChI key

HUJXGQILHAUCCV-MOROJQBDSA-N

assay

≥98% (HPLC)

form

solid

color

white

solubility

ethanol: >10 mg/mL (hot), DMSO: >5 mg/mL, H2O: insoluble, aqueous acid: insoluble, aqueous base: insoluble

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Application

IB-MECA has been used for intraocular pressure and corneal thickness measurements in rabbits.

Biochem/physiol Actions

Selective A3 adenosine receptor agonist.

Legal Information

Sold under license from the National Institutes of Health.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
042M4610V
117K4605
057K4631
051K4607

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John A Auchampach et al.
American journal of physiology. Heart and circulatory physiology, 285(2), H607-H613 (2003-04-12)
We examined the effect of the A3 adenosine receptor (AR) agonist IB-MECA on infarct size in an open-chest anesthetized dog model of myocardial ischemia-reperfusion injury. Dogs were subjected to 60 min of left anterior descending (LAD) coronary artery occlusion and
Athena M Keene et al.
Biochemical pharmacology, 80(2), 188-196 (2010-03-30)
Multivalent dendrimeric conjugates of GPCR ligands may have increased potency or selectivity in comparison to monomeric ligands, a phenomenon that was tested in a model of cytoprotection in mouse HL-1 cardiomyocytes. Quantitative RT-PCR indicated high expression levels of endogenous A(1)
P Mlejnek et al.
Acta physiologica (Oxford, England), 199(2), 171-179 (2010-02-04)
The sensitivity of cancer cells which exhibit multi-drug resistance phenotype to A3 adenosine receptor (A3AR) agonist N(6)-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide (IB-MECA) was studied. To establish direct relationship between P-glycoprotein (P-gp, ABCB1 and MDR1) expression and IB-MECA induced cell death, a straightforward method for
Lea Madi et al.
Experimental dermatology, 22(1), 74-77 (2012-10-24)
A3 adenosine receptor, A3AR, belongs to the Gi proteins coupled receptors. Activation of A3AR by its agonist, IB-MECA, decreases cAMP and was expected to reduce melanin level. Unexpectedly, B16 melanoma cells exposed to IB-MECA increased melanin levels in a dose-dependent
L Rath-Wolfson et al.
Clinical and experimental rheumatology, 24(4), 400-406 (2006-09-08)
The anti-inflammatory effect of adenosine is partially mediated via the A3 adenosine receptor (A3AR), a Gi protein associated cell surface receptor. The highly selective A3AR agonist, IB-MECA was earlier shown to prevent the clinical and pathological manifestations of arthritis in
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