LSP2-9166

LSP2-9166
Identifiers
	IUPAC name (2S)-2-amino-4-[[[4-(carboxymethoxy)-3-(trifluoromethoxy)phenyl]-hydroxymethyl]-hydroxyphosphoryl]butanoic acid;
PubChem CID	71042034;
ChemSpider	98651888;
Chemical and physical data
Formula	C14H17F3NO9P
Molar mass	431.257 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC(=C(C=C1C(O)P(=O)(CC[C@@H](C(=O)O)N)O)OC(F)(F)F)OCC(=O)O;
	InChI InChI=1S/C14H17F3NO9P/c15-14(16,17)27-10-5-7(1-2-9(10)26-6-11(19)20)13(23)28(24,25)4-3-8(18)12(21)22/h1-2,5,8,13,23H,3-4,6,18H2,(H,19,20)(H,21,22)(H,24,25)/t8-,13?/m0/s1; Key:NTRJZUQSNSIKLO-OADYLZGLSA-N;

LSP2-9166 is a drug which acts as a selective agonist for the group III metabotropic glutamate receptors, with a reasonably potent EC₅₀ of 70nM at mGluR₄ and 220nM at mGluR₇, and weaker activity of 1380nM at mGluR₆ and 4800nM at mGluR₈.^[1] It has anticonvulsant effects in animal studies,^[2]^[3] and reduces self-administration of various addictive drugs.^[4]^[5]^[6]

References

^ Acher FC, Cabayé A, Eshak F, Goupil-Lamy A, Pin JP (February 2022). "Metabotropic glutamate receptor orthosteric ligands and their binding sites". Neuropharmacology. 204: 108886. doi:10.1016/j.neuropharm.2021.108886. PMID 34813860.
^ Girard B, Tuduri P, Moreno MP, Sakkaki S, Barboux C, Bouschet T, et al. (September 2019). "The mGlu7 receptor provides protective effects against epileptogenesis and epileptic seizures". Neurobiology of Disease. 129: 13–28. doi:10.1016/j.nbd.2019.04.016. PMID 31051234.
^ Kovalenko AA, Zakharova MV, Schwarz AP, Dyomina AV, Zubareva OE, Zaitsev AV (March 2022). "Changes in Metabotropic Glutamate Receptor Gene Expression in Rat Brain in a Lithium-Pilocarpine Model of Temporal Lobe Epilepsy". International Journal of Molecular Sciences. 23 (5): 2752. doi:10.3390/ijms23052752. PMC 8910969. PMID 35269897.
^ Hajasova Z, Canestrelli C, Acher F, Noble F, Marie N (March 2018). "Role of mGlu7 receptor in morphine rewarding effects is uncovered by a novel orthosteric agonist". Neuropharmacology. 131: 424–430. doi:10.1016/j.neuropharm.2018.01.002. PMID 29307544. S2CID 3391450.
^ Lebourgeois S, Vilpoux C, Jeanblanc J, Acher F, Marie N, Noble F, Naassila M (May 2018). "Pharmacological activation of mGlu4 and mGlu7 receptors, by LSP2-9166, reduces ethanol consumption and relapse in rat". Neuropharmacology. 133: 163–170. doi:10.1016/j.neuropharm.2018.01.031. PMID 29378211. S2CID 3959313.
^ De Sa Nogueira D, Bourdy R, Filliol D, Quessada C, McCort-Tranchepain I, Acher F, et al. (November 2021). "LSP2-9166, an orthosteric mGlu4 and mGlu7 receptor agonist, reduces cocaine self-administration under a progressive ratio schedule in rats" (PDF). Neuroscience Letters. 764: 135603. doi:10.1016/j.neulet.2020.135603. PMID 33387661. S2CID 229724310.

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[pmid34813860-1] Acher FC, Cabayé A, Eshak F, Goupil-Lamy A, Pin JP (February 2022). "Metabotropic glutamate receptor orthosteric ligands and their binding sites". Neuropharmacology. 204: 108886. doi:10.1016/j.neuropharm.2021.108886. PMID 34813860.

[2] Girard B, Tuduri P, Moreno MP, Sakkaki S, Barboux C, Bouschet T, et al. (September 2019). "The mGlu7 receptor provides protective effects against epileptogenesis and epileptic seizures". Neurobiology of Disease. 129: 13–28. doi:10.1016/j.nbd.2019.04.016. PMID 31051234.

[pmid35269897-3] Kovalenko AA, Zakharova MV, Schwarz AP, Dyomina AV, Zubareva OE, Zaitsev AV (March 2022). "Changes in Metabotropic Glutamate Receptor Gene Expression in Rat Brain in a Lithium-Pilocarpine Model of Temporal Lobe Epilepsy". International Journal of Molecular Sciences. 23 (5): 2752. doi:10.3390/ijms23052752. PMC 8910969. PMID 35269897.

[4] Hajasova Z, Canestrelli C, Acher F, Noble F, Marie N (March 2018). "Role of mGlu7 receptor in morphine rewarding effects is uncovered by a novel orthosteric agonist". Neuropharmacology. 131: 424–430. doi:10.1016/j.neuropharm.2018.01.002. PMID 29307544. S2CID 3391450.

[5] Lebourgeois S, Vilpoux C, Jeanblanc J, Acher F, Marie N, Noble F, Naassila M (May 2018). "Pharmacological activation of mGlu4 and mGlu7 receptors, by LSP2-9166, reduces ethanol consumption and relapse in rat". Neuropharmacology. 133: 163–170. doi:10.1016/j.neuropharm.2018.01.031. PMID 29378211. S2CID 3959313.

[6] De Sa Nogueira D, Bourdy R, Filliol D, Quessada C, McCort-Tranchepain I, Acher F, et al. (November 2021). "LSP2-9166, an orthosteric mGlu4 and mGlu7 receptor agonist, reduces cocaine self-administration under a progressive ratio schedule in rats" (PDF). Neuroscience Letters. 764: 135603. doi:10.1016/j.neulet.2020.135603. PMID 33387661. S2CID 229724310.

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Identifiers

IUPAC name (2S)-2-amino-4-[[[4-(carboxymethoxy)-3-(trifluoromethoxy)phenyl]-hydroxymethyl]-hydroxyphosphoryl]butanoic acid
PubChem CID	71042034
ChemSpider	98651888
Chemical and physical data
Formula	C₁₄H₁₇F₃NO₉P
Molar mass	431.257 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1=CC(=C(C=C1C(O)P(=O)(CC[C@@H](C(=O)O)N)O)OC(F)(F)F)OCC(=O)O
InChI InChI=1S/C14H17F3NO9P/c15-14(16,17)27-10-5-7(1-2-9(10)26-6-11(19)20)13(23)28(24,25)4-3-8(18)12(21)22/h1-2,5,8,13,23H,3-4,6,18H2,(H,19,20)(H,21,22)(H,24,25)/t8-,13?/m0/s1 Key:NTRJZUQSNSIKLO-OADYLZGLSA-N