AZD-1940

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,[1] 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.[2][3]

AZD-1940
Clinical data
Routes of
administration		Oral
Legal status
Legal status
Identifiers
IUPAC name
  • N-{1-[(4,4-difluorocyclohexyl)methyl]-2-(1,1-dimethylethyl)-1H-benzimidazol-5-yl}ethanesulfonamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H29F2N3O2S
Molar mass413.53 g·mol−1
3D model (JSmol)
SMILES
  • CCS(=O)(=O)Nc1ccc2c(c1)nc(n2CC3CCC(CC3)(F)F)C(C)(C)C
InChI
  • InChI=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
  • Key:ZAGGGZCIFUQHOH-UHFFFAOYSA-N

See also

References
  1. Schou M, Varnäs K, Jucaite A, Gulyás B, Halldin C, Farde L (April 2013). "Radiolabeling of the cannabinoid receptor agonist AZD1940 with carbon-11 and PET microdosing in non-human primate". Nuclear Medicine and Biology. 40 (3): 410–4. doi:10.1016/j.nucmedbio.2012.10.011. PMID 23352602.
  2. Kalliomäki J, Segerdahl M, Webster L, Reimfelt A, Huizar K, Annas P, et al. (January 2013). "Evaluation of the analgesic efficacy of AZD1940, a novel cannabinoid agonist, on post-operative pain after lower third molar surgical removal". Scandinavian Journal of Pain. 4 (1): 17–22. doi:10.1016/j.sjpain.2012.08.004. PMID 29913883. S2CID 49302159.
  3. Kalliomäki J, Annas P, Huizar K, Clarke C, Zettergren A, Karlsten R, Segerdahl M (March 2013). "Evaluation of the analgesic efficacy and psychoactive effects of AZD1940, a novel peripherally acting cannabinoid agonist, in human capsaicin-induced pain and hyperalgesia". Clinical and Experimental Pharmacology & Physiology. 40 (3): 212–8. doi:10.1111/1440-1681.12051. PMID 23324098. S2CID 1630384.
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