MK-4409

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 2-[5-[5-(5-Chloropyridin-2-yl)sulfanyl-2-(4-fluorophenyl)-1,3-oxazol-4-yl]pyridin-2-yl]propan-2-ol

| image = MK-4409 structure.svg

| width = 200

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

| CAS_number = 1207745-58-1

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

| UNII = 77GX6MU9ZL

| ChEMBL = 1812717

| ATC_prefix = None

| ATC_suffix =

| PubChem = 53341130

| C=22 | H=17 | F=1 | N=3 | O=2 | S=1

| smiles = c3nc(C(O)(C)C)ccc3-c1nc(-c4ccc(F)cc4)oc1Sc(nc2)ccc2Cl

| ChemSpiderID = 25069631

| StdInChI = 1S/C22H17ClFN3O2S/c1-22(2,28)17-9-5-14(11-25-17)19-21(30-18-10-6-15(23)12-26-18)29-20(27-19)13-3-7-16(24)8-4-13/h3-12,28H,1-2H3

| StdInChIKey = DBZMCSVIITXLCC-UHFFFAOYSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

| legal_US = Investigational New Drug

| legal_status =

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}}

MK-4409 is an experimental drug which acts as a potent and selective inhibitor of the enzyme fatty acid amide hydrolase (FAAH), with an IC₅₀ of 11 nM, and both analgesic and antiinflammatory effects in animal studies. It was studied for the treatment of neuropathic pain and progressed to early stage human clinical trials by 2009.{{cite journal | vauthors = Chobanian HR, Guo Y, Liu P, Chioda MD, Fung S, Lanza TJ, Chang L, Bakshi RK, Dellureficio JP, Hong Q, McLaughlin M, Belyk KM, Krska SW, Makarewicz AK, Martel EJ, Leone JF, Frey L, Karanam B, Madeira M, Alvaro R, Shuman J, Salituro G, Terebetski JL, Jochnowitz N, Mistry S, McGowan E, Hajdu R, Rosenbach M, Abbadie C, Alexander JP, Shiao LL, Sullivan KM, Nargund RP, Wyvratt MJ, Lin LS, DeVita RJ | display-authors = 6 | title = Discovery of MK-4409, a Novel Oxazole FAAH Inhibitor for the Treatment of Inflammatory and Neuropathic Pain | journal = ACS Medicinal Chemistry Letters | volume = 5 | issue = 6 | pages = 717–21 | date = June 2014 | pmid = 24944750 | pmc = 4060928 | doi = 10.1021/ml5001239 }}{{cite web|url=https://www.merck.com/research/pipeline/MerckPipeline_Oct09_Final_10-15-09_10-Q.pdf|title=Merck Pipeline, Oct 2009|author=Merck|date=15 October 2009|work=Merck|access-date=18 January 2016|archive-date=20 October 2016|archive-url=https://web.archive.org/web/20161020181823/https://www.merck.com/research/pipeline/MerckPipeline_Oct09_Final_10-15-09_10-Q.pdf|url-status=dead}}