RQ-00202730

RQ-00202730
Identifiers
  • 2-[3-[1-[2-(dimethylamino)ethyl]-2-(2,2-dimethylpropyl)benzimidazol-5-yl]sulfonylazetidin-1-yl]ethanol
CAS Number
PubChem CID
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H34N4O3S
Molar mass422.59 g·mol−1
3D model (JSmol)
  • CC(C)(C)CC1=NC2=C(N1CCN(C)C)C=CC(=C2)S(=O)(=O)C3CN(C3)CCO
  • InChI=1S/C21H34N4O3S/c1-21(2,3)13-20-22-18-12-16(6-7-19(18)25(20)9-8-23(4)5)29(27,28)17-14-24(15-17)10-11-26/h6-7,12,17,26H,8-11,13-15H2,1-5H3
  • Key:OAYGNQGEUIFBFA-UHFFFAOYSA-N

RQ-00202730 is a benzimidazole derived drug that acts as a potent and highly selective agonist for the CB2 cannabinoid receptor, with a Ki value of 19nM at CB2 and more than 4000x selectivity over CB1, though it also shows some activity as an antagonist of the unrelated 5-HT2B serotonin receptor. It has analgesic and antiinflammatory effects in animal studies, and was developed for the treatment of irritable bowel syndrome, but was ultimately discontinued from development following disappointing results in Phase II clinical trials.[1][2][3]

  1. ^ Iwata Y, Ando K, Taniguchi K, Koba N, Sugiura A, Sudo M (January 2015). "Identification of a highly potent and selective CB2 agonist, RQ-00202730, for the treatment of irritable bowel syndrome". Bioorganic & Medicinal Chemistry Letters. 25 (2): 236–40. doi:10.1016/j.bmcl.2014.11.062. PMID 25499880.
  2. ^ "Research programme: irritable bowel syndrome therapeutics - RaQualia". AdisInsight. Springer Nature Switzerland AG. 23 February 2016.
  3. ^ Bow EW, Rimoldi JM (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry. 8: 17–39. doi:10.4137/PMC.S32171. PMC 4927043. PMID 27398024.