SIB-1757

SIB-1757
Identifiers
	IUPAC name 6-methyl-2-(phenylazo)-3-pyridinol;
CAS Number	31993-01-8 ;
PubChem CID	6849066;
ChemSpider	10654582;
CompTox Dashboard (EPA)	DTXSID00425754 ;
ECHA InfoCard	100.164.315
Chemical and physical data
Formula	C12H11N3O
Molar mass	213.240 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc1ccc(C)nc1\N=N\c2ccccc2;
	InChI InChI=1S/C12H11N3O/c1-9-7-8-11(16)12(13-9)15-14-10-5-3-2-4-6-10/h2-8,16H,1H3/b15-14+; Key:LOCPVWIREQIGNQ-CCEZHUSRSA-N;
	(verify)

SIB-1757 is a drug used in scientific research which was one of the first compounds developed that acts as a selective antagonist for the metabotropic glutamate receptor subtype mGluR₅.^[1] It has anti-hyperalgesia effects in animals.^[2] SIB-1757 along with other mGluR₅ antagonists has been shown to have neuroprotective and hepatoprotective effects,^[3]^[4] and it is also used to study the role of the mGluR₅ receptor in brain development.^[5]

References

^ Varney MA, Cosford ND, Jachec C, Rao SP, Sacaan A, Lin FF, Bleicher L, Santori EM, Flor PJ, Allgeier H, Gasparini F, Kuhn R, Hess SD, Veliçelebi G, Johnson EC (July 1999). "SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5". The Journal of Pharmacology and Experimental Therapeutics. 290 (1): 170–81. PMID 10381773.
^ Dogrul A, Ossipov MH, Lai J, Malan TP, Porreca F (October 2000). "Peripheral and spinal antihyperalgesic activity of SIB-1757, a metabotropic glutamate receptor (mGLUR(5)) antagonist, in experimental neuropathic pain in rats". Neuroscience Letters. 292 (2): 115–8. doi:10.1016/S0304-3940(00)01458-0. PMID 10998562. S2CID 7718378.
^ Storto M, Ngomba RT, Battaglia G, Freitas I, Griffini P, Richelmi P, Nicoletti F, Vairetti M (February 2003). "Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice". Journal of Hepatology. 38 (2): 179–87. doi:10.1016/S0168-8278(02)00384-7. PMID 12547406.
^ Fazal A, Parker F, Palmer AM, Croucher MJ (September 2003). "Characterisation of the actions of group I metabotropic glutamate receptor subtype selective ligands on excitatory amino acid release and sodium-dependent re-uptake in rat cerebrocortical minislices". Journal of Neurochemistry. 86 (6): 1346–58. doi:10.1046/j.1471-4159.2003.01932.x. PMID 12950444.
^ Bonsi P, Cuomo D, De Persis C, Centonze D, Bernardi G, Calabresi P, Pisani A (2005). "Modulatory action of metabotropic glutamate receptor (mGluR) 5 on mGluR1 function in striatal cholinergic interneurons". Neuropharmacology. 49. Suppl 1: 104–13. doi:10.1016/j.neuropharm.2005.05.012. PMID 16005029. S2CID 25980146.

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[pmid10381773-1] Varney MA, Cosford ND, Jachec C, Rao SP, Sacaan A, Lin FF, Bleicher L, Santori EM, Flor PJ, Allgeier H, Gasparini F, Kuhn R, Hess SD, Veliçelebi G, Johnson EC (July 1999). "SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5". The Journal of Pharmacology and Experimental Therapeutics. 290 (1): 170–81. PMID 10381773.

[pmid10998562-2] Dogrul A, Ossipov MH, Lai J, Malan TP, Porreca F (October 2000). "Peripheral and spinal antihyperalgesic activity of SIB-1757, a metabotropic glutamate receptor (mGLUR(5)) antagonist, in experimental neuropathic pain in rats". Neuroscience Letters. 292 (2): 115–8. doi:10.1016/S0304-3940(00)01458-0. PMID 10998562. S2CID 7718378.

[pmid12547406-3] Storto M, Ngomba RT, Battaglia G, Freitas I, Griffini P, Richelmi P, Nicoletti F, Vairetti M (February 2003). "Selective blockade of mGlu5 metabotropic glutamate receptors is protective against acetaminophen hepatotoxicity in mice". Journal of Hepatology. 38 (2): 179–87. doi:10.1016/S0168-8278(02)00384-7. PMID 12547406.

[pmid12950444-4] Fazal A, Parker F, Palmer AM, Croucher MJ (September 2003). "Characterisation of the actions of group I metabotropic glutamate receptor subtype selective ligands on excitatory amino acid release and sodium-dependent re-uptake in rat cerebrocortical minislices". Journal of Neurochemistry. 86 (6): 1346–58. doi:10.1046/j.1471-4159.2003.01932.x. PMID 12950444.

[pmid16005029-5] Bonsi P, Cuomo D, De Persis C, Centonze D, Bernardi G, Calabresi P, Pisani A (2005). "Modulatory action of metabotropic glutamate receptor (mGluR) 5 on mGluR1 function in striatal cholinergic interneurons". Neuropharmacology. 49. Suppl 1: 104–13. doi:10.1016/j.neuropharm.2005.05.012. PMID 16005029. S2CID 25980146.

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Identifiers

IUPAC name 6-methyl-2-(phenylazo)-3-pyridinol
CAS Number	31993-01-8^Y
PubChem CID	6849066
ChemSpider	10654582
CompTox Dashboard (EPA)	DTXSID00425754
ECHA InfoCard	100.164.315
Chemical and physical data
Formula	C₁₂H₁₁N₃O
Molar mass	213.240 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Oc1ccc(C)nc1\N=N\c2ccccc2
InChI InChI=1S/C12H11N3O/c1-9-7-8-11(16)12(13-9)15-14-10-5-3-2-4-6-10/h2-8,16H,1H3/b15-14+ Key:LOCPVWIREQIGNQ-CCEZHUSRSA-N
(verify)