Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C8H14O4S |
| Molecular Weight | 206.259 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC(CCCS)C(O)=O
InChI
InChIKey=FNLNSQHJKVQCBP-UHFFFAOYSA-N
InChI=1S/C8H14O4S/c9-7(10)4-3-6(8(11)12)2-1-5-13/h6,13H,1-5H2,(H,9,10)(H,11,12)
| Molecular Formula | C8H14O4S |
| Molecular Weight | 206.259 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Oral administration of the NAALADase inhibitor GPI-5693 attenuates cocaine-induced reinstatement of drug-seeking behavior in rats. | 2010-02-10 |
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| The preventive and therapeutic effects of GCPII (NAALADase) inhibition on painful and sensory diabetic neuropathy. | 2006-09-25 |
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| Structural optimization of thiol-based inhibitors of glutamate carboxypeptidase II by modification of the P1' side chain. | 2006-05-18 |
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| 2-MPPA, a selective glutamate carboxypeptidase II inhibitor, attenuates morphine tolerance but not dependence in C57/Bl mice. | 2005-12 |
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| The central nervous system effects, pharmacokinetics and safety of the NAALADase-inhibitor GPI 5693. | 2005-08 |
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| Enantiospecificity of glutamate carboxypeptidase II inhibition. | 2005-04-07 |
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| GCP II (NAALADase) inhibition suppresses mossy fiber-CA3 synaptic neurotransmission by a presynaptic mechanism. | 2004-01 |
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| Synthesis and biological evaluation of thiol-based inhibitors of glutamate carboxypeptidase II: discovery of an orally active GCP II inhibitor. | 2003-05-08 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Apr 01 17:00:54 GMT 2025
by
admin
on
Tue Apr 01 17:00:54 GMT 2025
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| Record UNII |
TV8F3S5KLG
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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Systematic Name | English | ||
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254737-29-6
Created by
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10198171
Created by
admin on Tue Apr 01 17:00:54 GMT 2025 , Edited by admin on Tue Apr 01 17:00:54 GMT 2025
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TV8F3S5KLG
Created by
admin on Tue Apr 01 17:00:54 GMT 2025 , Edited by admin on Tue Apr 01 17:00:54 GMT 2025
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GPI-5693
Created by
admin on Tue Apr 01 17:00:54 GMT 2025 , Edited by admin on Tue Apr 01 17:00:54 GMT 2025
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PRIMARY | Selective glutamate carboxypeptidase II (GCP II) inhibitor (IC50 = 90 nM). Selective for GCP II over NMDA, kainate and AMPA glutamate receptors and MMP-1, -2, -3, -7, -9, ACE and NEP metalloproteases. Antinociceptive in a rat model of neuropathic pain and protects against motor neuron death in familial amyotrophic lateral sclerosis mice. Orally bioavailable. |
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
We found that oral administration of GPI-5693 (15, 30, 60 mg/kg, p.o.) did not significantly alter intravenous cocaine self-administration under fixed-ratio (FR2) reinforcement, but significantly inhibited cocaine-induced reinstatement of the extinguished drug-seeking behavior. This inhibition was blocked by pretreatment with LY341495, a selective mGlu2/3 receptor antagonist. Two enantiomers of GPI-5693, also inhibited cocaine-induced reinstatement similar to GPI-5693.
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ACTIVE MOIETY |
Class: Neuroprotectant; Mechanism of Action: Glutamate carboxypeptidase II inhibitor, Highest Development Phases: Discontinued for Amyotrophic lateral sclerosis, Cerebral ischaemia, Diabetic neuropathy, Glaucoma, Neuropathic pain and Prostate cancer; Most Recent Event: 25 Jul 2006 This programme is still in active development with MGI GP
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