QUISQUALIC ACID

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16674916 | https://www.ncbi.nlm.nih.gov/pubmed/12501192 | https://www.ncbi.nlm.nih.gov/pubmed/17372356

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
Metabotropic glutamate receptor 1 25 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	Agonist 2678
Glutamate receptor 2 1 Target ID: P42262 Gene ID: 2891.0 Gene Symbol: GRIA2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12501192	Agonist 2678
Metabotropic glutamate receptor 5 39 Target ID: P41594 Gene ID: 2915.0 Gene Symbol: GRM5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16674916	Agonist 2678
Glutamate carboxypeptidase 2 1 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	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17372356	Preventing		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Conditions affecting the onset, severity, and progression of a spontaneous pain-like behavior after excitotoxic spinal cord injury.	2001 Aug	14622821
Cognitive effects of neurotoxic lesions of the nucleus basalis magnocellularis in rats: differential roles for corticopetal versus amygdalopetal projections.	2001 Jan	15111258
VEGA: a versatile program to convert, handle and visualize molecular structure on Windows-based PCs.	2002 Aug	12413030
Lead can inhibit NMDA-, K(+)-, QA/KA-induced increases in intracellular free Ca2+ in cultured rat hippocampal neurons.	2002 Dec	12642990
A pharmacological analysis of the contractile effects of glutamate on rat and human isolated gut smooth muscle strips.	2002 Dec	12616958
Group-I metabotropic glutamate receptors, mGlu1a and mGlu5a, couple to extracellular signal-regulated kinase (ERK) activation via distinct, but overlapping, signalling pathways.	2002 Dec	12437585
Identification and characterization of a novel splice variant of the metabotropic glutamate receptor 5 gene in human hippocampus and cerebellum.	2002 Dec 30	12531526
Characterization of mGluR5R, a novel, metabotropic glutamate receptor 5-related gene.	2002 Dec 30	12531512
Mechanism of activation and selectivity in a ligand-gated ion channel: structural and functional studies of GluR2 and quisqualate.	2002 Dec 31	12501192
The selective cyclooxygenase-2 inhibitor rofecoxib suppresses brain inflammation and protects cholinergic neurons from excitotoxic degeneration in vivo.	2003	12654342
Effects of agmatine, interleukin-10, and cyclosporin on spontaneous pain behavior after excitotoxic spinal cord injury in rats.	2003 Apr	14622710
A new acylglycosyl sterol from Quisqualis Fructus.	2003 Apr	12735684
Age-related differences in NMDA/metabotropic glutamate receptor binding in rat substantia nigra.	2003 Apr	12615085
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 Apr 4	12519791
Blockade of excitatory amino acid transporters in the rat hippocampus results in enhanced activation of group I and group III metabotropic glutamate receptors.	2003 Dec	14573381
Ionotropic glutamate receptors in cerebral microvascular endothelium are functionally linked to heme oxygenase.	2003 Feb	12571450
Neurohormonal and glutamatergic neuronal control of the cardioarterial valves in the isopod crustacean Bathynomus doederleini.	2003 Feb	12502764
Amino acid mutagenesis of the ligand binding site and the dimer interface of the metabotropic glutamate receptor 1. Identification of crucial residues for setting the activated state.	2003 Feb 7	12444084
Fluid flow in an animal model of post-traumatic syringomyelia.	2003 Jun	12800004
Nerve growth factor response to excitotoxic lesion of the cholinergic basal forebrain is slightly impaired in aged rats.	2003 Jun	12768358
Enhancing action of LSD on neuronal responsiveness to serotonin in a brain structure involved in obsessive-compulsive disorder.	2003 Mar	12899732
Metabotropic glutamate receptor activation enhances the activities of two types of Ca2+-activated k+ channels in rat hippocampal astrocytes.	2003 Mar 1	12629172
Mutational analysis and molecular modeling of the allosteric binding site of a novel, selective, noncompetitive antagonist of the metabotropic glutamate 1 receptor.	2003 Mar 7	12509432
Pharmacological properties of l-glutamate receptors associated with the crayfish hindgut.	2003 May	12720033
[3H]R214127: a novel high-affinity radioligand for the mGlu1 receptor reveals a common binding site shared by multiple allosteric antagonists.	2003 May	12695537
The role of excitotoxic injury in post-traumatic syringomyelia.	2003 Sep	14577866
N-methyl-D-aspartate receptor subunit expression and phosphorylation following excitotoxic spinal cord injury in rats.	2003 Sep 25	12946581
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	15026134
Interaction between intrathecal gabapentin and adenosine in the formalin test of rats.	2004 Aug	15308851
Characterization of a domoic acid binding site from Pacific razor clam.	2004 Aug 10	15261449
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 Aug 13	15184361
Effects of quisqualic acid on retinal ZENK expression induced by imposed defocus in the chick eye.	2004 Feb	15127932
Neuroprotective effects of nicotinamide after experimental spinal cord injury.	2004 Feb	14759952
Differentiation of substrate and non-substrate inhibitors of transport system xc(-): an obligate exchanger of L-glutamate and L-cystine.	2004 Feb	14680765
Nefopam blocks voltage-sensitive sodium channels and modulates glutamatergic transmission in rodents.	2004 Jul 9	15193535
Analogues of homoibotenic acid show potent and selective activity following sensitisation by quisqualic acid.	2004 Mar 19	15044041
A novel selective allosteric modulator potentiates the activity of native metabotropic glutamate receptor subtype 5 in rat forebrain.	2004 May	14747613
Spinal neurons involved in the generation of at-level pain following spinal injury in the rat.	2004 May 6	15135936
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 Oct	15605986
The Lathyrus excitotoxin beta-N-oxalyl-L-alpha,beta-diaminopropionic acid is a substrate of the L-cystine/L-glutamate exchanger system xc-.	2004 Oct 15	15476861
Excitatory amino acid induced oligodendrocyte cell death in vitro: receptor-dependent and -independent mechanisms.	2004 Sep	15312172
Active medullary control of atonia in week-old rats.	2005	15561443
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 Apr	15773922
Constitutive activity modulation of human metabotropic glutamate 5a receptors in HEK293 cells: a role for key amino-terminal cysteine residues.	2005 Apr	15700023
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 Apr	15608073
Crystal structures of the GluR5 and GluR6 ligand binding cores: molecular mechanisms underlying kainate receptor selectivity.	2005 Feb 17	15721240
Central neuropathic itch from spinal-cord cavernous hemangioma: a human case, a possible animal model, and hypotheses about pathogenesis.	2005 Jan	15621384
Distinct modulatory roles of sigma receptor subtypes on glutamatergic responses in the dorsal hippocampus.	2005 Jan	15499608
Interactions between ephrin-B and metabotropic glutamate 1 receptors in brain tissue and cultured neurons.	2005 Mar 2	15745950
Microsecond-to-millisecond conformational dynamics demarcate the GluR2 glutamate receptor bound to agonists glutamate, quisqualate, and AMPA.	2005 Mar 8	15736951

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

QUISQUALIC ACID

Common Name

English

.BETA.-(3,5-DIOXO-1,2,4-OXODIAZOLIDIN-2-YL)-L-ALANINE

Common Name

English

L-QUISQUALIC ACID

Common Name

English

QUISQUALIC ACID [MI]

Common Name

English

Code System Code Type Description

MESH

D016318