AZD-1940

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = N-{1-[(4,4-difluorocyclohexyl)methyl]-2-(1,1-dimethylethyl)-1H-benzimidazol-5-yl}ethanesulfonamide

| image = AZD1940_structure.png

| image_class = skin-invert-image

| width = 200

| tradename =

| legal_status = Investigational new drug

| routes_of_administration = Oral

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 881413-29-2

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

| UNII = 0J0035E9FT

| PubChem = 11675994

| ChemSpiderID = 9850723

| KEGG =

| C=20 | H=29 | F=2 | N=3 | O=2 | S=1

| smiles = CCS(=O)(=O)Nc1ccc2c(c1)nc(n2CC3CCC(CC3)(F)F)C(C)(C)C

| StdInChI = 1S/C20H29F2N3O2S/c1-5-28(26,27)24-15-6-7-17-16(12-15)23-18(19(2,3)4)25(17)13-14-8-10-20(21,22)11-9-14/h6-7,12,14,24H,5,8-11,13H2,1-4H3

| StdInChIKey = ZAGGGZCIFUQHOH-UHFFFAOYSA-N

}}

AZD-1940 is a drug developed by AstraZeneca, that is a peripherally selective cannabinoid agonist which binds with high affinity to both the CB₁ and CB₂ receptors. It was developed for the treatment of neuropathic pain, but while it showed good peripheral selectivity in animal studies,{{cite journal | vauthors = Schou M, Varnäs K, Jucaite A, Gulyás B, Halldin C, Farde L | title = Radiolabeling of the cannabinoid receptor agonist AZD1940 with carbon-11 and PET microdosing in non-human primate | journal = Nuclear Medicine and Biology | volume = 40 | issue = 3 | pages = 410–4 | date = April 2013 | pmid = 23352602 | doi = 10.1016/j.nucmedbio.2012.10.011 }} in human clinical trials it failed to show sufficient analgesic efficacy and produced unexpectedly strong side effects associated with central cannabinoid activity, and so was discontinued from further development.{{cite journal | vauthors = Kalliomäki J, Segerdahl M, Webster L, Reimfelt A, Huizar K, Annas P, Karlsten R, Quiding H | display-authors = 6 | title = Evaluation of the analgesic efficacy of AZD1940, a novel cannabinoid agonist, on post-operative pain after lower third molar surgical removal | journal = Scandinavian Journal of Pain | volume = 4 | issue = 1 | pages = 17–22 | date = January 2013 | pmid = 29913883 | doi = 10.1016/j.sjpain.2012.08.004 | s2cid = 49302159 }}{{cite journal | vauthors = Kalliomäki J, Annas P, Huizar K, Clarke C, Zettergren A, Karlsten R, Segerdahl M | title = Evaluation of the analgesic efficacy and psychoactive effects of AZD1940, a novel peripherally acting cannabinoid agonist, in human capsaicin-induced pain and hyperalgesia | journal = Clinical and Experimental Pharmacology & Physiology | volume = 40 | issue = 3 | pages = 212–8 | date = March 2013 | pmid = 23324098 | doi = 10.1111/1440-1681.12051 | s2cid = 1630384 }}