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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5137 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17204749 |
149.0 nM [Ki] | ||
Target ID: CHEMBL2888 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17204749 |
92.0 nM [Ki] | ||
Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19588471 |
80.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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Glutamate modulators as potential therapeutic drugs in schizophrenia and affective disorders. | 2013 Aug |
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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 |
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Pomaglumetad methionil: no significant difference as an adjunctive treatment for patients with prominent negative symptoms of schizophrenia compared to placebo. | 2013 Nov |
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Exploratory analysis for a targeted patient population responsive to the metabotropic glutamate 2/3 receptor agonist pomaglumetad methionil in schizophrenia. | 2015 Dec 1 |
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Successes, failures, and future prospects of prodrugs and their clinical impact. | 2019 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25890643
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21779400
rat primary astrocytes were treated with 100 uM LY404039
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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)