A-317491

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 571116

CAS#: 475205-49-3 (free acid)

Description: A-317491 is a potent and selective non-nucleotide antagonist of P2X3 and P2X2/3 receptors. A-317491 transiently attenuates cancer-induced bone pain in mice. A-317491 reverses inflammatory mechanical hyperalgesia through action at peripheral receptors in rats. A-317491 reduces chronic inflammatory and neuropathic pain in the rat.


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A-317491 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 571116
Name: A-317491
CAS#: 475205-49-3 (free acid)
Chemical Formula: C33H27NO8
Exact Mass: 565.1737
Molecular Weight: 565.58
Elemental Analysis: C, 70.08; H, 4.81; N, 2.48; O, 22.63


Related CAS #: 475205-49-3 (free acid)   Unknown (sodium)  

Synonym: A-317491; A317491; A 317491

IUPAC/Chemical Name: 1,2,4-Benzenetricarboxylic acid, 5-((((3-phenoxyphenyl)methyl)((1S)-1,2,3,4-tetrahydro-1-naphthalenyl)amino)carbonyl)-

InChi Key: VQGBOYBIENNKMI-LJAQVGFWSA-N

InChi Code: InChI=1S/C33H27NO8/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)/t29-/m0/s1

SMILES Code: O=C(C1=CC(C(N(CC2=CC=CC(OC3=CC=CC=C3)=C2)[C@H]4CCCC5=C4C=CC=C5)=O)=C(C(O)=O)C=C1C(O)=O)O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Wang WS, Tu WZ, Cheng RD, He R, Ruan LH, Zhang L, Gong YS, Fan XF, Hu J, Cheng B, Lai YP, Zou EM, Jiang SH. Electroacupuncture and A-317491 depress the transmission of pain on primary afferent mediated by the P2X3 receptor in rats with chronic neuropathic pain states. J Neurosci Res. 2014 Dec;92(12):1703-13. doi: 10.1002/jnr.23451. Epub 2014 Jul 17. PubMed PMID: 25041872.

2: Hansen RR, Nasser A, Falk S, Baldvinsson SB, Ohlsson PH, Bahl JM, Jarvis MF, Ding M, Heegaard AM. Chronic administration of the selective P2X3, P2X2/3 receptor antagonist, A-317491, transiently attenuates cancer-induced bone pain in mice. Eur J Pharmacol. 2012 Aug 5;688(1-3):27-34. doi: 10.1016/j.ejphar.2012.05.008. Epub 2012 May 22. PubMed PMID: 22634164.

3: Ito K, Iwami A, Katsura H, Ikeda M. Therapeutic effects of the putative P2X3/P2X2/3 antagonist A-317491 on cyclophosphamide-induced cystitis in rats. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jun;377(4-6):483-90. Epub 2007 Oct 5. PubMed PMID: 17917716.

4: Wu G, Whiteside GT, Lee G, Nolan S, Niosi M, Pearson MS, Ilyin VI. A-317491, a selective P2X3/P2X2/3 receptor antagonist, reverses inflammatory mechanical hyperalgesia through action at peripheral receptors in rats. Eur J Pharmacol. 2004 Nov 3;504(1-2):45-53. PubMed PMID: 15507220.

5: Jarvis MF, Bianchi B, Uchic JT, Cartmell J, Lee CH, Williams M, Faltynek C. [3H]A-317491, a novel high-affinity non-nucleotide antagonist that specifically labels human P2X2/3 and P2X3 receptors. J Pharmacol Exp Ther. 2004 Jul;310(1):407-16. Epub 2004 Mar 15. PubMed PMID: 15024037.

6: McGaraughty S, Wismer CT, Zhu CZ, Mikusa J, Honore P, Chu KL, Lee CH, Faltynek CR, Jarvis MF. Effects of A-317491, a novel and selective P2X3/P2X2/3 receptor antagonist, on neuropathic, inflammatory and chemogenic nociception following intrathecal and intraplantar administration. Br J Pharmacol. 2003 Dec;140(8):1381-8. Epub 2003 Nov 17. PubMed PMID: 14623769; PubMed Central PMCID: PMC1574160.

7: Neelands TR, Burgard EC, Uchic ME, McDonald HA, Niforatos W, Faltynek CR, Lynch KJ, Jarvis MF. 2', 3'-O-(2,4,6,trinitrophenyl)-ATP and A-317491 are competitive antagonists at a slowly desensitizing chimeric human P2X3 receptor. Br J Pharmacol. 2003 Sep;140(1):202-10. Epub 2003 Jul 29. PubMed PMID: 12967950; PubMed Central PMCID: PMC1574009.

8: Jarvis MF, Burgard EC, McGaraughty S, Honore P, Lynch K, Brennan TJ, Subieta A, Van Biesen T, Cartmell J, Bianchi B, Niforatos W, Kage K, Yu H, Mikusa J, Wismer CT, Zhu CZ, Chu K, Lee CH, Stewart AO, Polakowski J, Cox BF, Kowaluk E, Williams M, Sullivan J, Faltynek C. A-317491, a novel potent and selective non-nucleotide antagonist of P2X3 and P2X2/3 receptors, reduces chronic inflammatory and neuropathic pain in the rat. Proc Natl Acad Sci U S A. 2002 Dec 24;99(26):17179-84. Epub 2002 Dec 13. PubMed PMID: 12482951; PubMed Central PMCID: PMC139289.