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A2979

Sigma-Aldrich

A-317491 sodium salt hydrate

≥98% (HPLC), powder

Synonym(s):

5-[[[(3-Phenoxyphenyl)methyl][(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]carbonyl]-1,2,4-benzenetricarboxylic acid sodium salt hydrate

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About This Item

Empirical Formula (Hill Notation):
C33H27NO8 · xNa+ · yH2O
Molecular Weight:
565.57 (anhydrous free acid basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329770806
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 15 mg/mL, clear

originator

Abbott

SMILES string

[Na].[H]O[H].OC(=O)c1cc(C(O)=O)c(cc1C(O)=O)C(=O)N(Cc2cccc(Oc3ccccc3)c2)[C@H]4CCCc5ccccc45

InChI

1S/C33H27NO8.Na.H2O.H/c35-30(25-17-27(32(38)39)28(33(40)41)18-26(25)31(36)37)34(29-15-7-10-21-9-4-5-14-24(21)29)19-20-8-6-13-23(16-20)42-22-11-2-1-3-12-22;;;/h1-6,8-9,11-14,16-18,29H,7,10,15,19H2,(H,36,37)(H,38,39)(H,40,41);;1H2;/t29-;;;/m0.../s1

InChI key

VEMCGHRDAPMXLI-VYEUTZPBSA-N

Application

A-317491 sodium salt hydrate has been used to block the P2X3 receptor. It has also been used to block the increased membrane conductance.

Biochem/physiol Actions

A-317491 helps to decrease neuropathic and inflammatory pain by inhibiting the P2X3 receptor-mediated Ca2+ influx.
Novel P2X3 and P2X2/3 receptor antagonist

Features and Benefits

This compound is featured on the P2 Receptors: P2X Ion Channel Family page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Abbott. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Subject to U.S. Patent No. 6,831,193. Sold under license from Abbott Laboratories

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Effect of A-317491 delivered by glycolipid-like polymer micelles on endometriosis pain
Yuan M, et al.
International journal of nanomedicine, 12, 8171-8171 (2017)
Michael F Jarvis et al.
The Journal of pharmacology and experimental therapeutics, 310(1), 407-416 (2004-03-17)
A-317491 is a potent and selective antagonist of P2X3 and P2X(2/3) receptors. In the present studies, the ability of [3H]A-317491 to label recombinant human P2X(2/3) and P2X(3) receptors was characterized. Using membranes prepared from 1321N1 cells expressing P2X(2/3) receptors, [3H]A-317491
Michael F Jarvis et al.
Proceedings of the National Academy of Sciences of the United States of America, 99(26), 17179-17184 (2002-12-17)
P2X3 and P2X2/3 receptors are highly localized on peripheral and central processes of sensory afferent nerves, and activation of these channels contributes to the pronociceptive effects of ATP. A-317491 is a novel non-nucleotide antagonist of P2X3 and P2X2/3 receptor activation.
Early life allergen-induced mucus overproduction requires augmented neural stimulation of pulmonary neuroendocrine cell secretion
Barrios J, et al.
Faseb Journal, 31(9), 4117-4128 (2017)
Electrophysiological Evidence for Functional Astrocytic P2X3 Receptors in the Mouse Trigeminal Caudal Nucleus
Lee J, et al.
Experimental Neurobiology, 27(2), 88-93 (2018)
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