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{{Short description|Chemical compound}}
{{drugbox
{{Drugbox
⚫ | IUPAC_name = (E)-2-methyl-6-(2-phenylethenyl)pyridine
| Verifiedfields = changed
| image = SIB-1893_structure.png
| Watchedfields = changed
⚫ | width = 200
| verifiedrevid = 402053704
⚫ | CAS_number = 6266-99-5
⚫ | IUPAC_name = (E)-2-methyl-6-(2-phenylethenyl)pyridine
⚫ | ATC_prefix =
| image = SIB-1893.svg
⚫ | ATC_suffix =
⚫ | width = 200
⚫ | PubChem = 235382
| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫ | DrugBank =
| ChEMBL = 88612
⚫ | C=14|H=13|N=1
| molecular_weight = 195.259 g/mol
⚫ | smiles = c1ccccc1\C=C\c(nc2C)ccc2
⚫ | bioavailability =
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category=
⚫ | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫ | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫ | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫ | legal_status =
⚫ | routes_of_administration =
⚫ }}


<!--Clinical data-->
⚫ '''SIB-1893''' is a drug used in scientific research which was one of the first compounds developed that acts as a selective ] for the ] subtype ].<ref name="pmid10381773">{{cite journal |author=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 |title=SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5 |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=290 |issue=1 |pages=170–81 |year=1999 |month=July |pmid=10381773 |doi= |url=}}</ref> It has ] and ] effects,<ref name="pmid10854901">{{cite journal |author=Chapman AG, Nanan K, Williams M, Meldrum BS |title=Anticonvulsant activity of two metabotropic glutamate group I antagonists selective for the mGlu5 receptor: 2-methyl-6-(phenylethynyl)-pyridine (MPEP), and (E)-6-methyl-2-styryl-pyridine (SIB 1893) |journal=Neuropharmacology |volume=39 |issue=9 |pages=1567–74 |year=2000 |month=July |pmid=10854901 |doi= 10.1016/S0028-3908(99)00242-7|url=}}</ref> and reduces glutamate release.<ref name="pmid14982967">{{cite journal |author=Wang SJ, Sihra TS |title=Noncompetitive metabotropic glutamate5 receptor antagonist (E)-2-methyl-6-styryl-pyridine (SIB1893) depresses glutamate release through inhibition of voltage-dependent Ca2+ entry in rat cerebrocortical nerve terminals (synaptosomes) |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=309 |issue=3 |pages=951–8 |year=2004 |month=June |pmid=14982967 |doi=10.1124/jpet.103.064881 |url=}}</ref> It has also been found to act as a positive allosteric modulator of ].<ref name="pmid12684257">{{cite journal |author=Mathiesen JM, Svendsen N, Bräuner-Osborne H, Thomsen C, Ramirez MT |title=Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP |journal=British Journal of Pharmacology |volume=138 |issue=6 |pages=1026–30 |year=2003 |month=March |pmid=12684257 |pmc=1573757 |doi=10.1038/sj.bjp.0705159 |url=}}</ref>
| tradename =
⚫ | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_US = <!-- A / B / C / D / X -->
⚫ | pregnancy_category =
⚫ | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫ | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫ | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫ | legal_status =
⚫ | routes_of_administration =


<!--Pharmacokinetic data-->
⚫ == References ==
⚫ | bioavailability =
{{reflist}}
⚫ | protein_bound =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =


<!--Identifiers-->
{{Glutamate_receptor_ligands}}
| CAS_number_Ref = {{cascite|correct|CAS}}
⚫ | CAS_number = 7370-21-0
⚫ | ATC_prefix =
⚫ | ATC_suffix =
⚫ | PubChem = 235382
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4470920
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4X2F5X24UK


<!--Chemical data-->
⚫ | C=14 | H=13 | N=1
⚫ | smiles = c1ccccc1\C=C\c(nc2C)ccc2
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C14H13N/c1-12-6-5-9-14(15-12)11-10-13-7-3-2-4-8-13/h2-11H,1H3/b11-10+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SISOFUCTXZKSOQ-ZHACJKMWSA-N
⚫ }}


⚫ '''SIB-1893''' is a drug used in scientific research which was one of the first compounds developed that acts as a selective ] for the ] subtype ].<ref name="pmid10381773">{{cite journal |vauthors=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 |title=SIB-1757 and SIB-1893: selective, noncompetitive antagonists of metabotropic glutamate receptor type 5 |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=290 |issue=1 |pages=170–81 |date=July 1999 |pmid=10381773 }}</ref> It has ] and ] effects,<ref name="pmid10854901">{{cite journal |vauthors=Chapman AG, Nanan K, Williams M, Meldrum BS |title=Anticonvulsant activity of two metabotropic glutamate group I antagonists selective for the mGlu5 receptor: 2-methyl-6-(phenylethynyl)-pyridine (MPEP), and (E)-6-methyl-2-styryl-pyridine (SIB 1893) |journal=Neuropharmacology |volume=39 |issue=9 |pages=1567–74 |date=July 2000 |pmid=10854901 |doi= 10.1016/S0028-3908(99)00242-7|s2cid=21528282 }}</ref> and reduces glutamate release.<ref name="pmid14982967">{{cite journal |vauthors=Wang SJ, Sihra TS |title=Noncompetitive metabotropic glutamate5 receptor antagonist (E)-2-methyl-6-styryl-pyridine (SIB1893) depresses glutamate release through inhibition of voltage-dependent Ca2+ entry in rat cerebrocortical nerve terminals (synaptosomes) |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=309 |issue=3 |pages=951–8 |date=June 2004 |pmid=14982967 |doi=10.1124/jpet.103.064881 |s2cid=800526 }}</ref> It has also been found to act as a positive allosteric modulator of ].<ref name="pmid12684257">{{cite journal |vauthors=Mathiesen JM, Svendsen N, Bräuner-Osborne H, Thomsen C, Ramirez MT |title=Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP |journal=] |volume=138 |issue=6 |pages=1026–30 |date=March 2003 |pmid=12684257 |pmc=1573757 |doi=10.1038/sj.bjp.0705159 }}</ref>


⚫ ==References==
{{Reflist}}


{{Metabotropic glutamate receptor modulators}}



{{pharm-stub}}
] ]
]
]
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{{anticonvulsant-stub}}

Latest revision as of 19:11, 2 October 2024

Chemical compound Pharmaceutical compound
SIB-1893
Identifiers
IUPAC name
  • (E)-2-methyl-6-(2-phenylethenyl)pyridine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H13N
Molar mass195.265 g·mol
3D model (JSmol)
SMILES
  • c1ccccc1\C=C\c(nc2C)ccc2
InChI
  • InChI=1S/C14H13N/c1-12-6-5-9-14(15-12)11-10-13-7-3-2-4-8-13/h2-11H,1H3/b11-10+
  • Key:SISOFUCTXZKSOQ-ZHACJKMWSA-N
  (what is this?)  (verify)

SIB-1893 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. It has anticonvulsant and neuroprotective effects, and reduces glutamate release. It has also been found to act as a positive allosteric modulator of mGluR4.

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. Chapman AG, Nanan K, Williams M, Meldrum BS (July 2000). "Anticonvulsant activity of two metabotropic glutamate group I antagonists selective for the mGlu5 receptor: 2-methyl-6-(phenylethynyl)-pyridine (MPEP), and (E)-6-methyl-2-styryl-pyridine (SIB 1893)". Neuropharmacology. 39 (9): 1567–74. doi:10.1016/S0028-3908(99)00242-7. PMID 10854901. S2CID 21528282.
  3. Wang SJ, Sihra TS (June 2004). "Noncompetitive metabotropic glutamate5 receptor antagonist (E)-2-methyl-6-styryl-pyridine (SIB1893) depresses glutamate release through inhibition of voltage-dependent Ca2+ entry in rat cerebrocortical nerve terminals (synaptosomes)". The Journal of Pharmacology and Experimental Therapeutics. 309 (3): 951–8. doi:10.1124/jpet.103.064881. PMID 14982967. S2CID 800526.
  4. Mathiesen JM, Svendsen N, Bräuner-Osborne H, Thomsen C, Ramirez MT (March 2003). "Positive allosteric modulation of the human metabotropic glutamate receptor 4 (hmGluR4) by SIB-1893 and MPEP". British Journal of Pharmacology. 138 (6): 1026–30. doi:10.1038/sj.bjp.0705159. PMC 1573757. PMID 12684257.
Metabotropic glutamate receptor modulators
Group I
mGluR1Tooltip Metabotropic glutamate receptor 1
mGluR5Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2Tooltip Metabotropic glutamate receptor 2
mGluR3Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4Tooltip Metabotropic glutamate receptor 4
mGluR6Tooltip Metabotropic glutamate receptor 6
mGluR7Tooltip Metabotropic glutamate receptor 7
mGluR8Tooltip Metabotropic glutamate receptor 8
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators


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