AZD-1940

AZD-1940
Clinical data
Routes of; administration	Oral
Legal status
Legal status	Investigational new drug;
Identifiers
	IUPAC name N-{1-[(4,4-difluorocyclohexyl)methyl]-2-(1,1-dimethylethyl)-1H-benzimidazol-5-yl}ethanesulfonamide;
CAS Number	881413-29-2;
PubChem CID	11675994;
ChemSpider	9850723;
UNII	0J0035E9FT;
CompTox Dashboard (EPA)	DTXSID701114855 ;
Chemical and physical data
Formula	C20H29F2N3O2S
Molar mass	413.53 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References

^ 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.
^ 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.
^ 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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[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.

[1]

[2]

[3]

Clinical data

Routes of administration	Oral
Legal status
Legal status	Investigational new drug
Identifiers
IUPAC name N-{1-[(4,4-difluorocyclohexyl)methyl]-2-(1,1-dimethylethyl)-1H-benzimidazol-5-yl}ethanesulfonamide
CAS Number	881413-29-2
PubChem CID	11675994
ChemSpider	9850723
UNII	0J0035E9FT
CompTox Dashboard (EPA)	DTXSID701114855
Chemical and physical data
Formula	C₂₀H₂₉F₂N₃O₂S
Molar mass	413.53 g·mol⁻¹
3D model (JSmol)	Interactive image
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

AZD-1940

See also

References