Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C5H7N3O5 |
Molecular Weight | 189.1262 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CN1OC(=O)NC1=O)C(O)=O
InChI
InChIKey=ASNFTDCKZKHJSW-REOHCLBHSA-N
InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
Molecular Formula | C5H7N3O5 |
Molecular Weight | 189.1262 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Quisqualic acid is an agonist of (AMPA)-subtype glutamate receptor, GRIA2, and group I metabotropic glutamate receptors. Quisqualic acid has been shown to inhibit human glutamate carboxypeptidase II (GCPII), an enzyme occurs in the central nervous system as well as in human prostate (where it is called prostate-specific membrane antigen; PSMA). Inhibitors of this enzyme as was discovered can provide neuroprotection, but can also be useful for the detection, imaging, and treatment of prostate cancer.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q13255|||Q9NU10 Gene ID: 2911.0 Gene Symbol: GRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16674916 |
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Target ID: P42262 Gene ID: 2891.0 Gene Symbol: GRIA2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12501192 |
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Target ID: P41594 Gene ID: 2915.0 Gene Symbol: GRM5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16674916 |
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Target ID: Q04609|||Q16305 Gene ID: 2346.0 Gene Symbol: FOLH1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17372356 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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L-Quisqualic acid transport into hippocampal neurons by a cystine-sensitive carrier is required for the induction of quisqualate sensitization. | 2001 |
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Cell type-specific differences in the coupling of recombinant mGlu1alpha receptors to endogenous G protein sub-populations. | 2001 Apr |
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Spinal and supraspinal changes in opioid mRNA expression are related to the onset of pain behaviors following excitotoxic spinal cord injury. | 2001 Feb 1 |
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Expression of c-fos mRNA is increased and related to dynorphin mRNA expression following excitotoxic spinal cord injury in the rat. | 2001 Jul 20 |
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Reassessment of the Ca2+ sensing property of a type I metabotropic glutamate receptor by simultaneous measurement of inositol 1,4,5-trisphosphate and Ca2+ in single cells. | 2001 Jun 1 |
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Excitotoxic model of post-traumatic syringomyelia in the rat. | 2001 Sep 1 |
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Glutamate-mediated cytosolic calcium oscillations regulate a pulsatile prostaglandin release from cultured rat astrocytes. | 2003 Dec 1 |
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Fluid flow in an animal model of post-traumatic syringomyelia. | 2003 Jun |
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Structure of glutamate analogs that activate the ON bipolar cell metabotropic glutamate receptor in vertebrate retina. | 2003 May-Jun |
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Mutational analysis and molecular modeling of the binding pocket of the metabotropic glutamate 5 receptor negative modulator 2-methyl-6-(phenylethynyl)-pyridine. | 2003 Oct |
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A family of highly selective allosteric modulators of the metabotropic glutamate receptor subtype 5. | 2003 Sep |
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N-methyl-D-aspartate receptor subunit expression and phosphorylation following excitotoxic spinal cord injury in rats. | 2003 Sep 25 |
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Excitatory amino acid induced oligodendrocyte cell death in vitro: receptor-dependent and -independent mechanisms. | 2004 Sep |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1359473
Curator's Comment: Incubation of mouse brain sagittal slices with various concentrations of quisqualic acid resulted in significant increase in the leakage of lactate dehydrogenase and potassium from the slices into the medium. Prior incubation of mouse brain slices with NMDA (MK-801 or AP7) or non-NMDA receptor antagonists (GDEE or quinoxalinediones) protected against quisqualic acid-mediated toxicity. Slices prepared from animals pretreated in vivo with MK-801 (5 mg/kg b.wt.) were also resistant to the toxic effects of quisqualic acid, indicating the possible involvement of NMDA receptors in quisqualic acid toxicity.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:10:58 GMT 2025
by
admin
on
Mon Mar 31 19:10:58 GMT 2025
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Record UNII |
8OC22C1B99
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Record Status |
Validated (UNII)
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Record Version |
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QUISQUALIC ACID
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
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