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) |
|||
Target ID: P42262 Gene ID: 2891.0 Gene Symbol: GRIA2 Target Organism: Homo sapiens (Human) |
|||
Target ID: P41594 Gene ID: 2915.0 Gene Symbol: GRM5 Target Organism: Homo sapiens (Human) |
|||
Target ID: Q04609|||Q16305 Gene ID: 2346.0 Gene Symbol: FOLH1 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Group I metabotropic glutamate receptors, mGlu1a and mGlu5a, couple to cyclic AMP response element binding protein (CREB) through a common Ca2+ - and protein kinase C-dependent pathway. | 2005-04 |
|
| Constitutive activity modulation of human metabotropic glutamate 5a receptors in HEK293 cells: a role for key amino-terminal cysteine residues. | 2005-04 |
|
| A novel selective positive allosteric modulator of metabotropic glutamate receptor subtype 5 has in vivo activity and antipsychotic-like effects in rat behavioral models. | 2005-04 |
|
| Microsecond-to-millisecond conformational dynamics demarcate the GluR2 glutamate receptor bound to agonists glutamate, quisqualate, and AMPA. | 2005-03-08 |
|
| Interactions between ephrin-B and metabotropic glutamate 1 receptors in brain tissue and cultured neurons. | 2005-03-02 |
|
| Crystal structures of the GluR5 and GluR6 ligand binding cores: molecular mechanisms underlying kainate receptor selectivity. | 2005-02-17 |
|
| Central neuropathic itch from spinal-cord cavernous hemangioma: a human case, a possible animal model, and hypotheses about pathogenesis. | 2005-01 |
|
| Distinct modulatory roles of sigma receptor subtypes on glutamatergic responses in the dorsal hippocampus. | 2005-01 |
|
| Active medullary control of atonia in week-old rats. | 2005 |
|
| The Lathyrus excitotoxin beta-N-oxalyl-L-alpha,beta-diaminopropionic acid is a substrate of the L-cystine/L-glutamate exchanger system xc-. | 2004-10-15 |
|
| Abnormal metabotropic glutamate receptor expression and signaling in the cerebral cortex in diffuse Lewy body disease is associated with irregular alpha-synuclein/phospholipase C (PLCbeta1) interactions. | 2004-10 |
|
| Excitatory amino acid induced oligodendrocyte cell death in vitro: receptor-dependent and -independent mechanisms. | 2004-09 |
|
| Mutation-induced quisqualic acid and ibotenic acid affinity at the metabotropic glutamate receptor subtype 4: ligand selectivity results from a synergy of several amino acid residues. | 2004-08-13 |
|
| Characterization of a domoic acid binding site from Pacific razor clam. | 2004-08-10 |
|
| Interaction between intrathecal gabapentin and adenosine in the formalin test of rats. | 2004-08 |
|
| Nefopam blocks voltage-sensitive sodium channels and modulates glutamatergic transmission in rodents. | 2004-07-09 |
|
| Spinal neurons involved in the generation of at-level pain following spinal injury in the rat. | 2004-05-06 |
|
| A novel selective allosteric modulator potentiates the activity of native metabotropic glutamate receptor subtype 5 in rat forebrain. | 2004-05 |
|
| Analogues of homoibotenic acid show potent and selective activity following sensitisation by quisqualic acid. | 2004-03-19 |
|
| Effects of quisqualic acid on retinal ZENK expression induced by imposed defocus in the chick eye. | 2004-02 |
|
| Neuroprotective effects of nicotinamide after experimental spinal cord injury. | 2004-02 |
|
| Differentiation of substrate and non-substrate inhibitors of transport system xc(-): an obligate exchanger of L-glutamate and L-cystine. | 2004-02 |
|
| The effects of endogenous interleukin-10 on gray matter damage and the development of pain behaviors following excitotoxic spinal cord injury in the mouse. | 2004 |
|
| Glutamate-mediated cytosolic calcium oscillations regulate a pulsatile prostaglandin release from cultured rat astrocytes. | 2003-12-01 |
|
| Blockade of excitatory amino acid transporters in the rat hippocampus results in enhanced activation of group I and group III metabotropic glutamate receptors. | 2003-12 |
|
| PI3 kinase enhancer-Homer complex couples mGluRI to PI3 kinase, preventing neuronal apoptosis. | 2003-11 |
|
| Structure of glutamate analogs that activate the ON bipolar cell metabotropic glutamate receptor in vertebrate retina. | 2003-10-23 |
|
| Mutational analysis and molecular modeling of the binding pocket of the metabotropic glutamate 5 receptor negative modulator 2-methyl-6-(phenylethynyl)-pyridine. | 2003-10 |
|
| N-methyl-D-aspartate receptor subunit expression and phosphorylation following excitotoxic spinal cord injury in rats. | 2003-09-25 |
|
| The role of excitotoxic injury in post-traumatic syringomyelia. | 2003-09 |
|
| A family of highly selective allosteric modulators of the metabotropic glutamate receptor subtype 5. | 2003-09 |
|
| Fluid flow in an animal model of post-traumatic syringomyelia. | 2003-06 |
|
| Nerve growth factor response to excitotoxic lesion of the cholinergic basal forebrain is slightly impaired in aged rats. | 2003-06 |
|
| Pharmacological properties of l-glutamate receptors associated with the crayfish hindgut. | 2003-05 |
|
| [3H]R214127: a novel high-affinity radioligand for the mGlu1 receptor reveals a common binding site shared by multiple allosteric antagonists. | 2003-05 |
|
| Role of G protein-coupled receptor kinase 4 and beta-arrestin 1 in agonist-stimulated metabotropic glutamate receptor 1 internalization and activation of mitogen-activated protein kinases. | 2003-04-04 |
|
| Effects of agmatine, interleukin-10, and cyclosporin on spontaneous pain behavior after excitotoxic spinal cord injury in rats. | 2003-04 |
|
| A new acylglycosyl sterol from Quisqualis Fructus. | 2003-04 |
|
| Age-related differences in NMDA/metabotropic glutamate receptor binding in rat substantia nigra. | 2003-04 |
|
| Mutational analysis and molecular modeling of the allosteric binding site of a novel, selective, noncompetitive antagonist of the metabotropic glutamate 1 receptor. | 2003-03-07 |
|
| Metabotropic glutamate receptor activation enhances the activities of two types of Ca2+-activated k+ channels in rat hippocampal astrocytes. | 2003-03-01 |
|
| Enhancing action of LSD on neuronal responsiveness to serotonin in a brain structure involved in obsessive-compulsive disorder. | 2003-03 |
|
| Ionotropic glutamate receptors in cerebral microvascular endothelium are functionally linked to heme oxygenase. | 2003-02 |
|
| The selective cyclooxygenase-2 inhibitor rofecoxib suppresses brain inflammation and protects cholinergic neurons from excitotoxic degeneration in vivo. | 2003 |
|
| Identification and characterization of a novel splice variant of the metabotropic glutamate receptor 5 gene in human hippocampus and cerebellum. | 2002-12-30 |
|
| Characterization of mGluR5R, a novel, metabotropic glutamate receptor 5-related gene. | 2002-12-30 |
|
| Lead can inhibit NMDA-, K(+)-, QA/KA-induced increases in intracellular free Ca2+ in cultured rat hippocampal neurons. | 2002-12 |
|
| A pharmacological analysis of the contractile effects of glutamate on rat and human isolated gut smooth muscle strips. | 2002-12 |
|
| Conditions affecting the onset, severity, and progression of a spontaneous pain-like behavior after excitotoxic spinal cord injury. | 2001-08 |
|
| Cognitive effects of neurotoxic lesions of the nucleus basalis magnocellularis in rats: differential roles for corticopetal versus amygdalopetal projections. | 2001-01 |
Patents
Sample Use Guides
In Vitro Use Guide
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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