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Pomaglumetad Methionil

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Also known as: Ly2140023 monohydrate, 956385-05-0, Ly-2140023 monohydrate, Pomaglumetad metionilo, We665jb15r, (1r,4s,5s,6s)-4-(l-methionylamino)-2-thiabicyclo(3.1.0)hexane-4,6-dicarboxylic acid 2,2-dioxide monohydrate

Molecular Formula

C₁₂H₂₀N₂O₈S₂

Molecular Weight

384.4 g/mol

InChI Key

HQMAHCKDJKNYEK-LBMFEJOUSA-N

FDA UNII

WE665JB15R

a potent and selective methionil prodrug of the metabotropic glutamate

1 2D Structure

Pomaglumetad Methionil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,4S,5S,6S)-4-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-2,2-dioxo-26-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic acid;hydrate

2.1.2 InChI

InChI=1S/C12H18N2O7S2.H2O/c1-22-3-2-5(13)9(15)14-12(11(18)19)4-23(20,21)8-6(7(8)12)10(16)17;/h5-8H,2-4,13H2,1H3,(H,14,15)(H,16,17)(H,18,19);1H2/t5-,6+,7+,8-,12-;/m0./s1

2.1.3 InChI Key

HQMAHCKDJKNYEK-LBMFEJOUSA-N

2.2 Other Identifiers

2.2.1 UNII

WE665JB15R

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ly2140023 Monohydrate

2.3.2 Depositor-Supplied Synonyms

1. Ly2140023 Monohydrate

2. 956385-05-0

3. Ly-2140023 Monohydrate

4. Pomaglumetad Metionilo

5. We665jb15r

6. (1r,4s,5s,6s)-4-(l-methionylamino)-2-thiabicyclo(3.1.0)hexane-4,6-dicarboxylic Acid 2,2-dioxide Monohydrate

7. Dtxsid00212944

8. 4-(((2s)-2-amino-4-(methylthio)butanoyl)amino)-2-thiabicyclo(3.1.0)hexane-4,6-dicarboxylic Acid 2,2-dioxide Hydrate, 1r,4s,5s,6s

9. Pomaglumetadum Methionilum

10. Refchem:175219

11. Dtxcid30135435

12. 2-thiabicyclo(3.1.0)hexane-4,6-dicarboxylic Acid, 4-(((2s)-2-amino-4-(methylthio)-1-oxobutyl)amino)-, 2,2-dioxide, Hydrate (1:1), (1r,4s,5s,6s)-

13. 691-416-7

14. Pomaglumetad Methionil [usan]

15. Pomaglumetad Methionil (usan)

16. (1r,4s,5s,6s)-4-((s)-2-amino-4-(methylthio)butanamido)-2-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic Acid 2,2-dioxide Hydrate

17. (1r,4s,5s,6s)-4-[[(2s)-2-amino-4-methylsulfanylbutanoyl]amino]-2,2-dioxo-2lambda6-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic Acid;hydrate

18. Unii-we665jb15r

19. Pomaglumetad Methionil Hydrate

20. Orb1708826

21. Schembl1100180

22. Chembl2105707

23. Dtxsid10241907

24. Pomaglumetad Methionil Monohydrate

25. Akos040735205

26. Hy-105040

27. Cs-0024754

28. D09949

29. Q27292586

30. (1r,4s,5s,6s)-4-(2s-4-methylthio-2-aminobutanonyl)amino-2,2-dioxo-2lambda6-thia- Bicyclo(3.1.0)hexane-4,6-dicarboxylic Acid Monohydrate

31. (1r,4s,5s,6s)-4-(l-methionylamino)-2,2-dioxo-2gamma6-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic Acid-water (1:1)

32. (1r,4s,5s,6s)-4-(l-methionylamino)-2,2-dioxo-2lambda~6~-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic Acid--water (1/1)

33. (1r,4s,5s,6s)-4-[[(2s)-2-amino-4-methylsulfanylbutanoyl]amino]-2,2-dioxo-2

34. E6-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic Acid;hydrate

35. 2-thiabicyclo(3.1.0)hexane-4,6-dicarboxylic Acid, 4-(((2s)-2-amino-4-(methylthio)-1- Oxobutyl)amino)-, 2,2-dioxide, Hydrate (1:1), (1r,4s,5s,6s)-

2.4 Create Date

2012-03-21

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₂₀N₂O₈S₂
Molecular Weight	384.4 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	7
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	199
Heavy Atom Count	24
Formal Charge	0
Complexity	644
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in psychosis and schizophrenia and schizoaffective disorders.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

LY2140023 is an antipsychotic agent that is a metabotropic glutamate 2/3 receptor agonist. This agent has a new mechanism of action that is efficacious in treating schizophrenia and potentially other neuropsychiatric conditions. Once absorbed, LY2140023 is efficiently hydrolyzed to produce the active mGlu2/3 receptor agonist LY404039. LY404039 and other mGlu2/3 agonists do not directly interact with dopamine or serotonin (5-HT2A) receptors. However, 'functional' 5-HT2A receptor antagonism in the prefrontal cortex may represent a common mechanism shared by clinically effective atypical antipsychotics and mGlu2/3 receptor agonists, and may contribute to the antipsychotic actions of LY2140023.

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