Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C7H9NO6S |
| Molecular Weight | 235.214 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12[C@@H](C(O)=O)[C@]1([H])S(=O)(=O)C[C@@]2(N)C(O)=O
InChI
InChIKey=AVDUGNCTZRCAHH-MDASVERJSA-N
InChI=1S/C7H9NO6S/c8-7(6(11)12)1-15(13,14)4-2(3(4)7)5(9)10/h2-4H,1,8H2,(H,9,10)(H,11,12)/t2-,3-,4+,7+/m1/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24772351 | https://adisinsight.springer.com/drugs/800026989 | https://www.ncbi.nlm.nih.gov/pubmed/26861400https://www.ncbi.nlm.nih.gov/pubmed/17204749 | https://www.ncbi.nlm.nih.gov/pubmed/19588471 | https://www.ncbi.nlm.nih.gov/pubmed/18424625 | https://www.ncbi.nlm.nih.gov/pubmed/17384937 | https://www.ncbi.nlm.nih.gov/pubmed/20571979
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24772351 | https://adisinsight.springer.com/drugs/800026989 | https://www.ncbi.nlm.nih.gov/pubmed/26861400https://www.ncbi.nlm.nih.gov/pubmed/17204749 | https://www.ncbi.nlm.nih.gov/pubmed/19588471 | https://www.ncbi.nlm.nih.gov/pubmed/18424625 | https://www.ncbi.nlm.nih.gov/pubmed/17384937 | https://www.ncbi.nlm.nih.gov/pubmed/20571979
LY404039 [(-)-(1R,4S,5S,6S)-4-amino-2-sulfonylbicyclo[3.1.0]-hexane-4,6-dicarboxylic acid] is an agonist of orthosteric metabotropic glutamate receptor (mGluR)2/3. In addition, it acts as an agonist at dopamine D2 receptors. LY404039 demonstrated broad antipsychotic and anxiolytic efficacy across multiple animal models. LY-2140023 is a methionine amide prodrug of LY-404039 being developed by Eli Lilly & Co for the potential oral treatment of schizophrenia.
Originator
Sources: https://adisinsight.springer.com/drugs/800026989https://www.ncbi.nlm.nih.gov/pubmed/17204749 | https://www.ncbi.nlm.nih.gov/pubmed/17228865
Curator's Comment: # Eli Lilly
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacological and pharmacokinetic properties of a structurally novel, potent, and selective metabotropic glutamate 2/3 receptor agonist: in vitro characterization of agonist (-)-(1R,4S,5S,6S)-4-amino-2-sulfonylbicyclo[3.1.0]-hexane-4,6-dicarboxylic acid (LY404039). | 2007 Apr |
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| Synthesis and metabotropic glutamate receptor activity of S-oxidized variants of (-)-4-amino-2-thiabicyclo-[3.1.0]hexane-4,6-dicarboxylate: identification of potent, selective, and orally bioavailable agonists for mGlu2/3 receptors. | 2007 Jan 25 |
|
| Evidence for the role of metabotropic glutamate (mGlu)2 not mGlu3 receptors in the preclinical antipsychotic pharmacology of the mGlu2/3 receptor agonist (-)-(1R,4S,5S,6S)-4-amino-2-sulfonylbicyclo[3.1.0]hexane-4,6-dicarboxylic acid (LY404039). | 2008 Jul |
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| Comment on: "Adverse events in healthy subjects exposed to single and multiple doses of LY2140023 monohydrate" by Ayan-Oshodi et al (J Clin Psychopharmacol 2012;32[3]:408-411). | 2013 Apr |
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| Glutamate modulators as potential therapeutic drugs in schizophrenia and affective disorders. | 2013 Aug |
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| An agonist at glutamate and dopamine D2 receptors, LY404039. | 2013 Mar |
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| A long-term, phase 2, multicenter, randomized, open-label, comparative safety study of pomaglumetad methionil (LY2140023 monohydrate) versus atypical antipsychotic standard of care in patients with schizophrenia. | 2013 May 22 |
|
| Pomaglumetad Methionil (LY2140023 Monohydrate) and Aripiprazole in Patients with Schizophrenia: A Phase 3, Multicenter, Double-Blind Comparison. | 2014 |
|
| A short-term, multicenter, placebo-controlled, randomized withdrawal study of a metabotropic glutamate 2/3 receptor agonist using an electronic patient-reported outcome device in patients with schizophrenia. | 2014 Oct |
|
| In Vitro and Clinical Evaluations of the Drug-Drug Interaction Potential of a Metabotropic Glutamate 2/3 Receptor Agonist Prodrug with Intestinal Peptide Transporter 1. | 2017 Feb |
Sample Use Guides
Phase 3 study for the treatment of schizophrenia: 40 mg LY2140023 (prodrug of LY404039) administered orally; given twice daily for up to 4 weeks. At the discretion of the investigator, dose may be adjusted one time to 80 mg. 80 mg dose may be adjusted back to 40 mg one time. Mice: 3-30 mg/kg i.p.
Route of Administration:
Oral
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Pomaglumetad
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9834591
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DTXSID40212943
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531QUG7P9E
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635318-11-5
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94640
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CHEMBL375611
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
