I-AB-MECA

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H20IN7O4
Molecular Weight	525.3004
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=CN=C3NCC4=CC(I)=C(N)C=C4

InChI

InChIKey=LOGOEBMHHXYBID-MOROJQBDSA-N

InChI=1S/C18H20IN7O4/c1-21-17(29)14-12(27)13(28)18(30-14)26-7-25-11-15(23-6-24-16(11)26)22-5-8-2-3-10(20)9(19)4-8/h2-4,6-7,12-14,18,27-28H,5,20H2,1H3,(H,21,29)(H,22,23,24)/t12-,13+,14-,18+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8190112/
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23487508 | https://www.ncbi.nlm.nih.gov/pubmed/8896425 | https://www.ncbi.nlm.nih.gov/pubmed/10987829 | https://www.ncbi.nlm.nih.gov/pubmed/9037389

I-AB-MECA is iodinated form of parent compound - adenosine derivative, 4-aminobenzyl-5'-N-methylcarboxamidoadenosine (AB-MECA). AB-MECA i a potent agonist of adenosine A3 receptor agonist. 125I-labeled AB-MECA is widely used in in vitro pharmacological studies of adenosine A3 receptor as a refernece ligand. In addition I-AB-MECA is usefull in vitro autoradiography to map adenosine A3 receptor distribution tissues. I-AB-MECA bound to the rat adenosine A1 receptor and canine adenosine A2a receptor.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adenosine A3 receptor 24 Target ID: CHEMBL3360 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8126704\|https://www.ncbi.nlm.nih.gov/pubmed/9459566	Agonist 2678	14.0 nM [Ki]
Adenosine A3 receptor 24 Target ID: CHEMBL256 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10987829 \| https://www.ncbi.nlm.nih.gov/pubmed/12527805	Agonist 2678	1.3 nM [Kd]
Adenosine A1 receptor 50 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8190112/	Agonist 2678	3.42 nM [Kd]
Adenosine A2a receptor 30 Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8190112/	Agonist 2678	25.1 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
125I-4-aminobenzyl-5'-N-methylcarboxamidoadenosine, a high affinity radioligand for the rat A3 adenosine receptor.	1994 May	8190112
Activation of A3 adenosine receptors on human eosinophils elevates intracellular calcium.	1996 Nov 1	8896425
[125I]4-aminobenzyl-5'-N-methylcarboxamidoadenosine (125I)AB-MECA) labels multiple adenosine receptor subtypes in rat brain.	1997 Jan 16	9037389
Binding affinity of adenosine receptor agonists and antagonists at human cloned A3 adenosine receptors.	1998	9714428
Activation and Desensitization of Rat A(3)-Adenosine Receptors by Selective Adenosine Derivatives and Xanthine-7-Ribosides.	1998 Jun 1	23487508
Pharmacological analysis of calcium responses mediated by the human A3 adenosine receptor in monocyte-derived dendritic cells and recombinant cells.	2003 Feb	12527805
Species comparison of adenosine receptor subtypes in brain and testis.	2008 May	17987385
The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages.	2010 Mar	20136829

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

the maximal inhibition of LPS-stimulated TNF-α production by human lung macrophages by AB-MECA was 26 ± 6% at 10 µM

Name

Type

Language

I-AB-MECA

Common Name

English

.BETA.-D-RIBOFURANURONAMIDE, 1-(6-(((4-AMINO-3-IODOPHENYL)METHYL)AMINO)-9H-PURIN-9-YL)-1-DEOXY-N-METHYL-

Systematic Name

English

AB-MECA

Common Name

English

Code System Code Type Description

CAS

152918-27-9