A P2X3 and P2X2/3 receptor antagonist
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A-317491

Item No. 19256

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[[[(3-phenoxyphenyl)methyl][(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]carbonyl]-1,2,4-benzenetricarboxylic acid
CAS Number
475205-49-3
Molecular Formula
C33H27NO8
Formula Weight
565.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
OC(C1=C(C(N([C@H]2CCCC3=C2C=CC=C3)CC4=CC=CC(OC5=CC=CC=C5)=C4)=O)C=C(C(O)=O)C(C(O)=O)=C1)=O
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
InChi Key
VQGBOYBIENNKMI-LJAQVGFWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $40

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    5 mg

    $124

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    10 mg

    $228

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    25 mg

    $329

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    Product Description

    A-317491 is a non-nucleotide antagonist of the purinergic receptors P2X3 and P2X2/3 (Kis = 22-92 nM in a calcium influx assay) that is selective over other purinergic and neurotransmitter receptors, ion channels, and enzymes (IC50s = >10 µM).1 It reduces thermal hyperalgesia induced by complete Freund’s adjuvant in rats (ED50 = 30 µmol/kg, s.c.) and nociceptive responses to chemically-induced pain. Chronic administration of A-317491 (30 µmol/kg, twice daily) reduces early, but not late, phase pain in a mouse model of bone cancer.2 A-317491 does not readily cross the blood-brain barrier and reduces pain responses when applied topically in a rat model of inflammatory pain, indicating that it acts primarily at peripheral purinergic receptors.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jarvis, M.F., Burgard, E.C., McGaraughty, S., et al. 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. USA 99(26), 17179-17184 (2002).

    2. Hansen, R.R., Nasser, A., Falk, S., et al. Chronic administration of the selective P2X3, P2X2/3 receptor antagonist, A-317491, transiently attenuates cancer-induced bone pain in mice. Eur. J. Pharmacol. 688(1-3), 27-34 (2012).

    3. Wu, G., Whiteside, G.T., Lee, G., et al. A-317491, a selective P2X3/P2X2/3 receptor antagonist, reverses inflammatory mechanical hyperalgesia through action at peripheral receptors in rats. Eur. J. Pharmacol. 504(1-2), 45-53 (2004).