LY-320,135

LY-320,135
Identifiers
	IUPAC name 4-[6-methoxy-2-(4-methoxyphenyl)1-benzofuran-3-carbonyl]benzonitrile;
CAS Number	176977-56-3;
PubChem CID	5311257;
IUPHAR/BPS	742;
ChemSpider	4470772;
UNII	CJY03984CT;
ChEMBL	ChEMBL411481;
CompTox Dashboard (EPA)	DTXSID901027464 ;
ECHA InfoCard	100.190.302
Chemical and physical data
Formula	C24H17NO4
Molar mass	383.403 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c3cc(OC)ccc3-c2oc1cc(OC)ccc1c2C(=O)c4ccc(C#N)cc4;
	InChI InChI=1S/C24H17NO4/c1-27-18-9-7-17(8-10-18)24-22(20-12-11-19(28-2)13-21(20)29-24)23(26)16-5-3-15(14-25)4-6-16/h3-13H,1-2H3; Key:RYNSGDFWBJWWSZ-UHFFFAOYSA-N;
	(verify)

LY-320,135 is a drug used in scientific research which acts as a selective antagonist of the cannabinoid receptor CB₁. It was developed by Eli Lilly and Company in the 1990s.

LY-320,135 displays fairly good selectivity, with a binding affinity for CB₁ around 70x stronger than for CB₂,^[1] but both its potency and selectivity are modest compared to newer agents, and at higher doses it also binds to a range of non-cannabinoid receptors. However LY-320,135 is still fairly widely used in research, particularly for elucidating the mechanisms by which many CB₁ antagonists act as inverse agonists at higher doses.^[2]

References

^ Felder CC, Joyce KE, Briley EM, Glass M, Mackie KP, Fahey KJ, et al. (January 1998). "LY320135, a novel cannabinoid CB1 receptor antagonist, unmasks coupling of the CB1 receptor to stimulation of cAMP accumulation". The Journal of Pharmacology and Experimental Therapeutics. 284 (1): 291–7. PMID 9435190.
^ Pertwee RG (February 2005). "Inverse agonism and neutral antagonism at cannabinoid CB1 receptors". Life Sciences. 76 (12): 1307–24. doi:10.1016/j.lfs.2004.10.025. PMID 15670612.

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[1] Felder CC, Joyce KE, Briley EM, Glass M, Mackie KP, Fahey KJ, et al. (January 1998). "LY320135, a novel cannabinoid CB1 receptor antagonist, unmasks coupling of the CB1 receptor to stimulation of cAMP accumulation". The Journal of Pharmacology and Experimental Therapeutics. 284 (1): 291–7. PMID 9435190.

[2] Pertwee RG (February 2005). "Inverse agonism and neutral antagonism at cannabinoid CB1 receptors". Life Sciences. 76 (12): 1307–24. doi:10.1016/j.lfs.2004.10.025. PMID 15670612.

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Identifiers

IUPAC name 4-[6-methoxy-2-(4-methoxyphenyl)1-benzofuran-3-carbonyl]benzonitrile
CAS Number	176977-56-3
PubChem CID	5311257
IUPHAR/BPS	742
ChemSpider	4470772
UNII	CJY03984CT
ChEMBL	ChEMBL411481
CompTox Dashboard (EPA)	DTXSID901027464
ECHA InfoCard	100.190.302
Chemical and physical data
Formula	C₂₄H₁₇NO₄
Molar mass	383.403 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c3cc(OC)ccc3-c2oc1cc(OC)ccc1c2C(=O)c4ccc(C#N)cc4
InChI InChI=1S/C24H17NO4/c1-27-18-9-7-17(8-10-18)24-22(20-12-11-19(28-2)13-21(20)29-24)23(26)16-5-3-15(14-25)4-6-16/h3-13H,1-2H3 Key:RYNSGDFWBJWWSZ-UHFFFAOYSA-N
(verify)