Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C33H27NO8 |
| Molecular Weight | 565.5694 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC(C(O)=O)=C(C=C1C(O)=O)C(=O)N(CC2=CC=CC(OC3=CC=CC=C3)=C2)[C@H]4CCCC5=C4C=CC=C5
InChI
InChIKey=VQGBOYBIENNKMI-LJAQVGFWSA-N
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
A-317491 (ABT-202) is a non-nucleotide antagonist of P2X3 and P2X2/3 receptor activation. A-317491 potently blocked recombinant human and rat P2X3 and P2X2/3 receptor-mediated calcium flux (Ki = 22-92 nM) and was highly selective (IC50 >10 uM) over other P2 receptors and other neurotransmitter receptors, ion channels, and enzymes. A-317491 also blocked native P2X3 and P2X2/3 receptors in rat dorsal root ganglion neurons. Blockade of P2X3 containing channels was stereospecific because the R-enantiomer (A-317344) of A-317491 was significantly less active at P2X3 and P2X2/3 receptors. A-317491 dose-dependently (ED50 = 30 umolkg s.c.) reduced complete Freund's adjuvant-induced thermal hyperalgesia in the rat. Studies indicate that the P2X3 receptor is implicated in both neuropathic and inflammatory pain. P2X3 receptor is a promising target for therapeutic intervention in cancer patients for pain management. ABT-202 had been in phase I clinical trials by Abbott and NeuroSearch for the treatment of pain. However, this research has been discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Roles of peripheral P2X and P2Y receptors in the development of melittin-induced nociception and hypersensitivity. | 2008-10 |
|
| Therapeutic effects of the putative P2X3/P2X2/3 antagonist A-317491 on cyclophosphamide-induced cystitis in rats. | 2008-06 |
|
| 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. | 2002-12-24 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: A-317491 was also administered intravenously (3-10 mg kg(-1) A-317491 i.v.) in chronic constriction injury (CCI)- and sham-operated rats
https://www.ncbi.nlm.nih.gov/pubmed/16770326
Rats: in the rat Freund's complete adjuvant model of inflammatory pain, s.c. administration of A-317491 dose-dependently reversed mechanical hyperalgesia. Maximum percent reversal (72%) was seen 3 h after administration at 10 mg/kg.
Route of Administration:
Other
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DTXSID40197185
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9829395
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475205-49-3
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H327N08IPV
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ACTIVE MOIETY
