:RO4491533

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-methyl-8-trifluoromethyl-1,3-dihydrobenzo[b][1,4]diazepin-2-one

| image = RO4491533.svg

| width = 222

| tradename =

| pregnancy_category =

| legal_status = Non-regulated

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 6226

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 579482-31-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = HF59BT62UG

| ATC_prefix = None

| ATC_suffix =

| PubChem = 11158623

| ChemSpiderID = 9333726

| smiles = n3c(C)cc(cc3C)-c(ccc4)cc4C(=Nc1cc2C)CC(=O)Nc1cc2C(F)(F)F

| C = 24 | H = 20 | F = 3 | N = 3 | O = 1

| StdInChI = 1S/C24H20F3N3O/c1-13-7-21-22(11-19(13)24(25,26)27)30-23(31)12-20(29-21)17-6-4-5-16(10-17)18-8-14(2)28-15(3)9-18/h4-11H,12H2,1-3H3,(H,30,31)

| StdInChIKey = LYTVXCQQTLUEQR-UHFFFAOYSA-N

}}

RO-4491533 is a drug developed by Hoffmann-La Roche which acts as a potent and selective negative allosteric modulator for group II of the metabotropic glutamate receptors (mGluR_2/3), being equipotent at mGluR₂ and mGluR₃ but without activity at other mGluR subtypes. In animal studies, RO-4491533 produced antidepressant effects and reversed the effects of the mGluR_2/3 agonist LY-379,268 with similar efficacy but slightly lower potency than the mGluR_2/3 antagonist LY-341,495.{{cite journal | vauthors = Campo B, Kalinichev M, Lambeng N, El Yacoubi M, Royer-Urios I, Schneider M, Legrand C, Parron D, Girard F, Bessif A, Poli S, Vaugeois JM, Le Poul E, Celanire S | display-authors = 6 | title = Characterization of an mGluR2/3 negative allosteric modulator in rodent models of depression | journal = Journal of Neurogenetics | volume = 25 | issue = 4 | pages = 152–66 | date = December 2011 | pmid = 22091727 | doi = 10.3109/01677063.2011.627485 | s2cid = 207440972 }} A number of related compounds are known, with similar effects in vitro and a fairly well characterized structure-activity relationship.{{cite journal | vauthors = Hemstapat K, Da Costa H, Nong Y, Brady AE, Luo Q, Niswender CM, Tamagnan GD, Conn PJ | display-authors = 6 | title = A novel family of potent negative allosteric modulators of group II metabotropic glutamate receptors | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 322 | issue = 1 | pages = 254–64 | date = July 2007 | pmid = 17416742 | doi = 10.1124/jpet.106.117093 | s2cid = 3820477 }}