A-317491 sodium
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MedKoo CAT#: 526701

CAS#: Unknown (sodium)

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.

Chemical Structure

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A-317491 sodium
CAS# Unknown (sodium)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 526701
Name: A-317491 sodium
CAS#: Unknown (sodium)
Chemical Formula: C33H24NNa3O8
Exact Mass: 565.17
Molecular Weight: 631.120
Elemental Analysis: C, 62.76; H, 3.83; N, 2.22; Na, 10.92; O, 20.27

Price and Availability

Size Price Availability Quantity
10mg USD 150
25mg USD 250
50mg USD 450
100mg USD 750
250mg USD 1450
500mg USD 1950
1g USD 3250
2g USD 4850
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Related CAS #: Unknown (sodium)   475205-49-3 (free acid)    

Synonym: A-317491; A 317491; A317491.

IUPAC/Chemical Name: sodium (S)-5-((3-phenoxybenzyl)(1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)benzene-1,2,4-tricarboxylate

InChi Key: OIPSITXEGDHODK-VYEUTZPBSA-K

InChi Code: InChI=1S/C33H27NO8.3Na/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);;;/q;3*+1/p-3/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-].[Na+].[Na+].[Na+]

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, not in water

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).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Selective, high affinity P2X3 and P2X2/3 antagonist.
In vitro activity: TBD
In vivo activity: P2X3 agonist-activated currents in the DRG neurons were recorded by whole cell patch clamp. The experimental results revealed that the P2X3 agonist α,βme-ATP (10 μM)-activated currents in DRG neurons cultured with gp120 were higher than those in controls (Fig. 4A). The inhibitory effect of A317491 on α,βme-ATP-induced currents in DRG rat neurons cultured with gp120 was larger than that for control (Fig. 4B) (n = 8, p < 0.01). These results further support the opinion that the activation of P2X3 receptor may be involved in HIV-associated neuropathic pain. Reference: Brain Res Bull. 2017 Apr;130:81-89. https://pubmed.ncbi.nlm.nih.gov/28065732/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 61.0 96.57

Preparing Stock Solutions

The following data is based on the product molecular weight 631.12 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Yi Z, Rao S, Ouyang S, Bai Y, Yang J, Ma Y, Han X, Wu B, Zou L, Jia T, Zhao S, Hu X, Lei Q, Gao Y, Liu S, Xu H, Zhang C, Liang S, Li G. A317491 relieved HIV gp120-associated neuropathic pain involved in P2X3 receptor in dorsal root ganglia. Brain Res Bull. 2017 Apr;130:81-89. doi: 10.1016/j.brainresbull.2017.01.002. Epub 2017 Jan 5. PMID: 28065732. 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. PMID: 22634164.
In vitro protocol: TBD
In vivo protocol: 1. Yi Z, Rao S, Ouyang S, Bai Y, Yang J, Ma Y, Han X, Wu B, Zou L, Jia T, Zhao S, Hu X, Lei Q, Gao Y, Liu S, Xu H, Zhang C, Liang S, Li G. A317491 relieved HIV gp120-associated neuropathic pain involved in P2X3 receptor in dorsal root ganglia. Brain Res Bull. 2017 Apr;130:81-89. doi: 10.1016/j.brainresbull.2017.01.002. Epub 2017 Jan 5. PMID: 28065732. 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. PMID: 22634164.

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1: Yuan M, Ding S, Meng T, Lu B, Shao S, Zhang X, Yuan H, Hu F. Effect of A-317491 delivered by glycolipid-like polymer micelles on endometriosis pain. Int J Nanomedicine. 2017 Nov 9;12:8171-8183. doi: 10.2147/IJN.S146569. PMID: 29184406; PMCID: PMC5687452.


2: 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. doi: 10.1016/j.ejphar.2004.09.056. PMID: 15507220.


3: 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. doi: 10.1073/pnas.252537299. Epub 2002 Dec 13. PMID: 12482951; PMCID: PMC139289.


4: 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. doi: 10.1124/jpet.103.064907. Epub 2004 Mar 15. PMID: 15024037.


5: 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. doi: 10.1038/sj.bjp.0705574. Epub 2003 Nov 17. PMID: 14623769; PMCID: PMC1574160.


6: 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. PMID: 25041872.


7: 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. doi: 10.1007/s00210-007-0197-z. Epub 2007 Oct 5. PMID: 17917716.


8: 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. PMID: 22634164.


9: 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. doi: 10.1038/sj.bjp.0705411. Epub 2003 Jul 29. PMID: 12967950; PMCID: PMC1574009.


10: McGaraughty S, Jarvis MF. Antinociceptive properties of a non-nucleotide P2X3/P2X2/3 receptor antagonist. Drug News Perspect. 2005 Oct;18(8):501-7. doi: 10.1358/dnp.2005.18.8.942082. PMID: 16391720.


11: Donnelly-Roberts D, McGaraughty S, Shieh CC, Honore P, Jarvis MF. Painful purinergic receptors. J Pharmacol Exp Ther. 2008 Feb;324(2):409-15. doi: 10.1124/jpet.106.105890. Epub 2007 Nov 27. PMID: 18042830.


12: Burnstock G. The therapeutic potential of purinergic signalling. Biochem Pharmacol. 2018 May;151:157-165. doi: 10.1016/j.bcp.2017.07.016. Epub 2017 Jul 21. PMID: 28735873.


13: de Melo Aquino B, da Silva Dos Santos DF, Jorge CO, Marques ACS, Teixeira JM, Parada CA, Oliveira-Fusaro MCG. P2X3 receptors contribute to muscle pain induced by static contraction by a mechanism dependent on neutrophil migration. Purinergic Signal. 2019 Jun;15(2):167-175. doi: 10.1007/s11302-019-09659-0. Epub 2019 May 21. PMID: 31115830; PMCID: PMC6635523.


14: Sharp CJ, Reeve AJ, Collins SD, Martindale JC, Summerfield SG, Sargent BS, Bate ST, Chessell IP. Investigation into the role of P2X(3)/P2X(2/3) receptors in neuropathic pain following chronic constriction injury in the rat: an electrophysiological study. Br J Pharmacol. 2006 Jul;148(6):845-52. doi: 10.1038/sj.bjp.0706790. Epub 2006 Jun 12. PMID: 16770326; PMCID: PMC1617075.


15: Ma X, Xu T, Xu H, Jiang W. Blockade and reversal of spinal morphine tolerance by P2X3 receptor antagonist. Behav Pharmacol. 2015 Apr;26(3):260-7. doi: 10.1097/FBP.0000000000000105. PMID: 25350728.


16: Gever JR, Soto R, Henningsen RA, Martin RS, Hackos DH, Panicker S, Rubas W, Oglesby IB, Dillon MP, Milla ME, Burnstock G, Ford AP. AF-353, a novel, potent and orally bioavailable P2X3/P2X2/3 receptor antagonist. Br J Pharmacol. 2010 Jul;160(6):1387-98. doi: 10.1111/j.1476-5381.2010.00796.x. PMID: 20590629; PMCID: PMC2938810.


17: McGaraughty S, Honore P, Wismer CT, Mikusa J, Zhu CZ, McDonald HA, Bianchi B, Faltynek CR, Jarvis MF. Endogenous opioid mechanisms partially mediate P2X3/P2X2/3-related antinociception in rat models of inflammatory and chemogenic pain but not neuropathic pain. Br J Pharmacol. 2005 Sep;146(2):180-8. doi: 10.1038/sj.bjp.0706346. PMID: 16041397; PMCID: PMC1576275.


18: Zhuang J, Gao X, Wei W, Pelleg A, Xu F. Intralaryngeal application of ATP evokes apneic response mainly via acting on P2X3 (P2X2/3) receptors of the superior laryngeal nerve in postnatal rats. J Appl Physiol (1985). 2021 Sep 1;131(3):986-996. doi: 10.1152/japplphysiol.00091.2021. Epub 2021 Jul 29. PMID: 34323594; PMCID: PMC8461810.


19: King BF. P2X3 receptors participate in purinergic inhibition of gastrointestinal smooth muscle. Auton Neurosci. 2021 Sep;234:102830. doi: 10.1016/j.autneu.2021.102830. Epub 2021 Jun 5. PMID: 34116466.


20: Lu SH, Groat WC, Lin AT, Chen KK, Chang LS. Evaluation of purinergic mechanism for the treatment of voiding dysfunction: a study in conscious spinal cord-injured rats. J Chin Med Assoc. 2007 Oct;70(10):439-44. doi: 10.1016/s1726-4901(08)70035-2. PMID: 17962144; PMCID: PMC3119078.