RQ-00202730

RQ-00202730
Identifiers
	IUPAC name 2-[3-[1-[2-(dimethylamino)ethyl]-2-(2,2-dimethylpropyl)benzimidazol-5-yl]sulfonylazetidin-1-yl]ethanol;
CAS Number	1236006-97-5 [PubChem];
PubChem CID	46852212;
ChEMBL	ChEMBL3357391;
CompTox Dashboard (EPA)	DTXSID101336641 ;
Chemical and physical data
Formula	C21H34N4O3S
Molar mass	422.59 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 K_i 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-HT_2B 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]

References

^ 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.
^ "Research programme: irritable bowel syndrome therapeutics - RaQualia". AdisInsight. Springer Nature Switzerland AG. 23 February 2016.
^ 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.

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[pmid25499880-1] 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.

[pmid27398024-3] 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.

[1]

[2]

[3]

See also

References