RQ-00202730

Chemical structure
RQ-00202730
Identifiers
  • 2-[3-[1-[2-(dimethylamino)ethyl]-2-(2,2-dimethylpropyl)benzimidazol-5-yl]sulfonylazetidin-1-yl]ethanol
PubChem CID
  • 46852212
ChEMBL
  • ChEMBL3357391
Chemical and physical data
FormulaC21H34N4O3S
Molar mass422.59 g·mol−1
3D model (JSmol)
  • Interactive image
  • CC(C)(C)CC1=NC2=C(N1CCN(C)C)C=CC(=C2)S(=O)(=O)C3CN(C3)CCO
InChI
  • 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]

See also

  • AZ-11713908
  • AZD-1940
  • JTE 7-31
  • MCHB-1

References

  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.
  • v
  • t
  • e
Phytocannabinoids
(comparison)
Cannabibutols
  • CBB
Cannabichromenes
Cannabicyclols
  • CBL
    • CBLA
  • CBLB
  • CBLP
    • CBLPA
  • CBLV
    • CBLVA
Cannabidiols
Cannabielsoins
  • CBE
    • CBEA
      • CBEA-A
      • CBEA-B
  • CBEB
  • CBEP
    • CBEPA
  • CBEV
Cannabigerols
  • CBG
    • CBGA
    • CBGB
    • CBGBA
    • CBGM
      • CBGAM
  • CBGP
    • CBGPA
  • CBNR
    • CBNRA
      • CBNRA-A
  • CBGV
    • CBGVA
      • CBGVA-A
  • CBGQ
Cannabiphorols
  • CBP
Cannabinols
  • CBN
    • CBNA
    • CBN-C1
    • CBN-C2
    • CBN-C4
    • CBNM
  • CBND
    • CBNDA
  • CBNP
    • CBNPA
  • CBVD
    • CBVDA
Cannabitriols
  • CBT
    • CBTA
  • CBTB
  • CBTV
    • CBTVA
  • CBTP
    • CBTPA
Cannabivarins
Delta-8-tetrahydrocannabinols
  • Delta-8-THC
    • Delta-8-THCA
      • Delta-8-THCA-A
  • Delta-8-THCB
  • Delta-8-THCP
  • Delta-8-THCV
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
EndocannabinoidsSynthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Hydrocarbons
Indazole carboxamides
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Pyrrolobenzoxazines
Quinolinyl esters
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Tetramethylcyclo-
propylindoles
Others
Allosteric CBRTooltip Cannabinoid receptor ligandsEndocannabinoid
enhancers
(inactivation inhibitors)Anticannabinoids
(antagonists/inverse
agonists/antibodies)
Stub icon

This cannabinoid related article is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e