SIB-1757

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]

SIB-1757
Identifiers
IUPAC name
  • 6-methyl-2-(phenylazo)-3-pyridinol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.164.315
Chemical and physical data
FormulaC12H11N3O
Molar mass213.240 g·mol−1
3D model (JSmol)
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)

References
  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.
  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.
  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.
  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.
  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.


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