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=C(N)C(I)=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

Molecular Formula	C18H20IN7O4
Molecular Weight	525.3004
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/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 2752	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 2752	1.3 nM [Kd]
Adenosine A1 receptor 54 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8190112/	Agonist 2752	3.42 nM [Kd]
Adenosine A2a receptor 31 Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8190112/	Agonist 2752	25.1 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages.	2010-03	20136829
Species comparison of adenosine receptor subtypes in brain and testis.	2008-05	17987385
Pharmacological analysis of calcium responses mediated by the human A3 adenosine receptor in monocyte-derived dendritic cells and recombinant cells.	2003-02	12527805
Agonist-induced internalization and recycling of the human A(3) adenosine receptors: role in receptor desensitization and resensitization.	2000-10	10987829
Activation and Desensitization of Rat A3-Adenosine Receptors by Selective Adenosine Derivatives and Xanthine-7-Ribosides.	1998-06-01	23487508
Binding affinity of adenosine receptor agonists and antagonists at human cloned A3 adenosine receptors.	1998	9714428
[125I]4-aminobenzyl-5'-N-methylcarboxamidoadenosine (125I)AB-MECA) labels multiple adenosine receptor subtypes in rat brain.	1997-01-16	9037389
Activation of A3 adenosine receptors on human eosinophils elevates intracellular calcium.	1996-11-01	8896425
125I-4-aminobenzyl-5'-N-methylcarboxamidoadenosine, a high affinity radioligand for the rat A3 adenosine receptor.	1994-05	8190112

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:15:09 GMT 2025` Edited by `admin` on `Mon Mar 31 22:15:09 GMT 2025`
Record UNII	9WR19428J3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AB-MECA

Preferred Name

English

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

Code System Code Type Description

CAS

152918-27-9