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SML2269

Sigma-Aldrich

LY404039

≥98% (HPLC)

Synonym(s):

(1R,4S,5S,6S)-4-Amino-2-thiabicyclo[3.1.0]hexane-4,6-dicarboxylic acid 2,2-dioxide, (–)-(1R,4S,5S,6S)-4-Amino-2-sulfonylbicyclo[3.1.0]hexane-4,6-dicarboxylic acid, LY 404039, LY-404,039, LY-404039

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About This Item

Empirical Formula (Hill Notation):
C7H9NO6S
CAS Number:
635318-11-5
Molecular Weight:
235.21
MDL number:
MFCD11974011
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -69 to -79°, c = 1.0 in 1 M NaOH

color

white to gray

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

[H][C@]1([C@@](C(O)=O)(N)C2)[C@@]([C@@H]1C(O)=O)([H])S2(=O)=O

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

InChI key

AVDUGNCTZRCAHH-MDASVERJSA-N

Biochem/physiol Actions

LY404039 is a potent and selective group II metabotropic glutamate receptors mGluR2/3 agonist (Ki = 15 nM against against [3H]LY341495 for binding rat neurons; Ki = 149 nM and 92 nM, respectively, using membrane from human mGluR2- or mGluR3-expressing cells) with >100-fold selectivity over 16 other receptors/transproters, including iGluRs and EAAT1/2/3. LY404039 inhibits forskolin-stimulated c-AMP production in RGT cells expressing human mGluR2 (EC50 = 23 nM) or mGluR3 (EC50 = 48 nM) with little or no potency toward mGluR1a/5a/4a/6/7a/8a-expressing cells (EC50 >10 μM). LY404039 is orally available (Cmax 1528.5 ng/mL, Tmax 2 h; 10 mg/kg p.o. in rats) and exhibits antipsychotic and anxiolytic efficacy in rats (3-30 mg/kg) in vivo.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Linda M Rorick-Kehn et al.
The Journal of pharmacology and experimental therapeutics, 321(1), 308-317 (2007-01-06)
Group II metabotropic glutamate (mGlu) receptor agonists, including (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylate monohydrate (LY354740) and (-)-2-oxa-4-aminobicyclo[3.1.0]hexane-4,6-dicarboxylate (LY379268), have demonstrated efficacy in animal models of anxiety and schizophrenia, and LY354740 decreased anxiety in human subjects. Herein, we report the in vitro pharmacological profile and
Linda M Rorick-Kehn et al.
Psychopharmacology, 193(1), 121-136 (2007-03-27)
Data from both preclinical and clinical studies have provided proof of concept that modulation of limbic and forebrain glutamate, via mGlu2/3 receptor agonists, might provide therapeutic benefits in many psychiatric disorders including schizophrenia and anxiety. The aim of this study
Ramin Ekhteiari Salmas et al.
ACS chemical neuroscience, 8(6), 1404-1415 (2017-03-09)
Dopamine receptor D2 (D2R) plays an important role in the human central nervous system and is a focal target of antipsychotic agents. The D2HighR and D2LowR dimeric models previously developed by our group are used to investigate the prediction of
Zachary A Rodd et al.
Behavioural brain research, 171(2), 207-215 (2006-05-09)
Metabotropic glutamate (mGlu) receptors have been shown to mediate a number of behaviors including emotionality and responsivity to stress as demonstrated by efficacy in preclinical and clinical studies. The objective of this study was to assess the effects of the
Christian C Felder et al.
The Journal of pharmacology and experimental therapeutics, 361(1), 190-197 (2017-02-01)
LY2812223 [(1R,2S,4R,5R,6R)-2-amino-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]hexane-2,6-dicarboxylic acid] was identified via structure-activity studies arising from the potent metabotropic glutamate mGlu2/3 receptor agonist LY354740 [(+)-2-aminobicyclo[3.1.0] hexane-2,6-dicarboxylic acid] as an mGlu2-preferring agonist. This pharmacology was determined using stably transfected cells containing either the human mGlu2 or mGlu3
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