GYKI 52466: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 381811860

| Reference=

|ImageFile=GYKI 52466.

|ImageSize=

| ImageAlt = Skeletal formula

| ImageFile1 = GYKI-52,466 molecule spacefill.png

| ImageSize1 = 160

| ImageAlt1 = Space-filling model of GYKI-52,466

| PIN = 4-(8-Methyl-2''H'',9''H''-[1,3]dioxolo[4,5-''h''][2,3]benzodiazepin-5-yl)aniline

|OtherNames=

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 4210

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=102771-26-6

| CASNo1_Ref = {{cascite|changed|??}}

| CASNo1 = 192065-56-8

| CASNo1_Comment = (HCl salt)

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 471V8NZ5X3

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 79560

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C15040

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 3417

| PubChem=3538

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 275006

| SMILES=CC1=NN=C(C2=CC3=C(C=C2C1)OCO3)C4=CC=C(C=C4)N

| InChI = 1/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3

| InChIKey = LFBZZHVSGAHQPP-UHFFFAOYAH

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = LFBZZHVSGAHQPP-UHFFFAOYSA-N

|Section2={{Chembox Properties

| C=17 | H=15 | N=3 | O=2

| Appearance=Yellow solid (HCl salt)

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=>10 mg/mL (HCl salt)

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

'''GYKI 52466''' is a 2,3-[[benzodiazepine]] that acts as an ionotropic [[glutamate]] [[receptor (biochemistry)|receptor]] antagonist, which is a non-competitive [[AMPA receptor]] [[receptor antagonist|antagonist]] (IC₅₀ values are 10-20, ~ 450 and >> 50 μM for AMPA-, kainate- and NMDA-induced responses respectively), orally-active [[anticonvulsant]], and [[skeletal muscle]] [[Muscle relaxant|relaxant]].<ref>{{cite journal | doi = 10.1016/s0306-4522(98)00109-2 | title = Allosteric regulation of α-amino-3-hydroxy-5-methyl-4-isoxazole-propionate receptors by thiocyanate and cyclothiazide at a common modulatory site distinct from that of 2,3-benzodiazepines | year = 1998 | last1 = Donevan | first1 = S.D | last2 = Rogawski | first2 = M.A | journal = Neuroscience | volume = 87 | issue = 3 | pages = 615–629 | pmid = 9758228 | s2cid = 14817743 }}</ref><ref>{{cite journal | doi = 10.1016/0896-6273(93)90241-i | title = GYKI 52466, a 2,3-benzodiazepine, is a highly selective, noncompetitive antagonist of AMPA/Kainate receptor responses | year = 1993 | last1 = Donevan | first1 = Sean D. | last2 = Rogawski | first2 = Michael A. | journal = Neuron | volume = 10 | issue = 1 | pages = 51–59 | pmid = 7678966 | s2cid = 16011527 }}</ref><ref>{{cite journal | doi = 10.1016/0014-2999(89)90579-7 | title = Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466 | year = 1989 | last1 = Tarnawa | first1 = István | last2 = Farkas | first2 = Sándor | last3 = Berzsenyi | first3 = Pál | last4 = Pataki | first4 = Ágnes | last5 = Andrási | first5 = Ferenc | journal = European Journal of Pharmacology | volume = 167 | issue = 2 | pages = 193–199 | pmid = 2574112 }}</ref><ref>{{cite journal | doi = 10.1073/pnas.091113598 | title = Glutamate antagonists limit tumor growth | year = 2001 | last1 = Rzeski | first1 = W. | last2 = Turski | first2 = L. | last3 = Ikonomidou | first3 = C. | journal = Proceedings of the National Academy of Sciences | volume = 98 | issue = 11 | pages = 6372–6377 | pmid = 11331750 | pmc = 33475 | doi-access = free }}</ref> Unlike conventional 1,4-benzodiazepines, GYKI 52466 and related 2,3-benzodiazepines do not act on [[GABAA receptor|GABA_A receptors]].<ref>{{cite journal | doi = 10.1016/0896-6273(95)90253-8 | title = Selective antagonism of AMPA receptors unmasks kainate receptor-mediated responses in hippocampal neurons | year = 1995 | last1 = Paternain | first1 = Ana V. | last2 = Morales | first2 = Miguel | last3 = Lerma | first3 = Juan | journal = Neuron | volume = 14 | issue = 1 | pages = 185–189 | pmid = 7826635 | s2cid = 6037517 | doi-access = free }}</ref> Like other AMPA receptor antagonists, GYKI 52466 has anticonvulsant and [[neuroprotective]] properties.<ref>{{cite journal | doi = 10.1016/s0361-9230(01)00516-0 | title = Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655 | year = 2001 | last1 = Szabados | first1 = Tamás | last2 = Gigler | first2 = Gábor | last3 = Gacsályi | first3 = István | last4 = Gyertyán | first4 = István | last5 = Lévay | first5 = György | journal = Brain Research Bulletin | volume = 55 | issue = 3 | pages = 387–391 | pmid = 11489346 | s2cid = 23142293 }}</ref>

====

*[[GYKI 52895]], another 2,3-benzodiazepine with other than GABAergic function

*[[Tifluadom]]

*[[Lufuradom]]

==References==

{{}}

{{Ionotropic glutamate receptor modulators}}

{{Benzodiazepines}}

[[Category:AMPA receptor ]]

[[Category:Anticonvulsants]]

[[Category:Muscle relaxants]]