Cannabinor

Cannabinor
Identifiers
	IUPAC name (E)-4-[2-[(1S,2S,5S)-6,6-dimethyl-4-oxo-2-bicyclo[3.1.1]heptanyl]-3-hydroxy-5-(2-methyloctan-2-yl)phenoxy]-4-oxobut-2-enoic acid;
CAS Number	573981-31-4;
PubChem CID	10174045;
DrugBank	DB05048;
ChemSpider	8349550;
UNII	O8E148Q90M;
ChEMBL	ChEMBL3234035;
CompTox Dashboard (EPA)	DTXSID701019168 ;
Chemical and physical data
Formula	C28H36O6
Molar mass	468.590 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCC(C)(C)C1=CC(=C(C(=C1)OC(=O)/C=C/C(=O)O)[C@H]2CC(=O)[C@H]3C[C@@H]2C3(C)C)O;
	InChI InChI=1S/C28H38O6/c1-6-7-8-9-12-27(2,3)17-13-22(30)26(23(14-17)34-25(33)11-10-24(31)32)18-15-21(29)20-16-19(18)28(20,4)5/h10-11,13-14,18-20,30H,6-9,12,15-16H2,1-5H3,(H,31,32)/b11-10+/t18-,19-,20+/m0/s1; Key:GSTZHANFXAKPSE-MXTREEOPSA-N;

Cannabinor (PRS-211,375) is a drug which acts as a potent and selective cannabinoid CB₂ receptor agonist.^[1]^[2] It is classed as a "nonclassical" cannabinoid with a chemical structure similar to that of cannabidiol. It has a CB₂ affinity of 17.4 nM vs 5,585 nM at CB₁, giving it over 300× selectivity for CB₂.^[3] It showed analgesic effects in animal studies especially in models of neuropathic pain, but failed in Phase IIb human clinical trials due to lack of efficacy.^[4]

References

^ Gratzke C, Streng T, Stief CG, Downs TR, Alroy I, Rosenbaum JS, Andersson KE, Hedlund P (June 2010). "Effects of cannabinor, a novel selective cannabinoid 2 receptor agonist, on bladder function in normal rats". European Urology. 57 (6): 1093–100. doi:10.1016/j.eururo.2010.02.027. PMID 20207474.
^ Gratzke C, Streng T, Stief CG, Alroy I, Limberg BJ, Downs TR, et al. (February 2011). "Cannabinor, a selective cannabinoid-2 receptor agonist, improves bladder emptying in rats with partial urethral obstruction". The Journal of Urology. 185 (2): 731–6. doi:10.1016/j.juro.2010.09.080. PMID 21168864.
^ 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.
^ Nevalainen T (2013). "Recent development of CB2 selective and peripheral CB1/CB2 cannabinoid receptor ligands". Current Medicinal Chemistry. 21 (2): 187–203. doi:10.2174/09298673113206660296. PMID 24164198.

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[pmid20207474-1] Gratzke C, Streng T, Stief CG, Downs TR, Alroy I, Rosenbaum JS, Andersson KE, Hedlund P (June 2010). "Effects of cannabinor, a novel selective cannabinoid 2 receptor agonist, on bladder function in normal rats". European Urology. 57 (6): 1093–100. doi:10.1016/j.eururo.2010.02.027. PMID 20207474.

[2] Gratzke C, Streng T, Stief CG, Alroy I, Limberg BJ, Downs TR, et al. (February 2011). "Cannabinor, a selective cannabinoid-2 receptor agonist, improves bladder emptying in rats with partial urethral obstruction". The Journal of Urology. 185 (2): 731–6. doi:10.1016/j.juro.2010.09.080. PMID 21168864.

[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.

[4] Nevalainen T (2013). "Recent development of CB2 selective and peripheral CB1/CB2 cannabinoid receptor ligands". Current Medicinal Chemistry. 21 (2): 187–203. doi:10.2174/09298673113206660296. PMID 24164198.

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Identifiers

IUPAC name (E)-4-[2-[(1S,2S,5S)-6,6-dimethyl-4-oxo-2-bicyclo[3.1.1]heptanyl]-3-hydroxy-5-(2-methyloctan-2-yl)phenoxy]-4-oxobut-2-enoic acid
CAS Number	573981-31-4
PubChem CID	10174045
DrugBank	DB05048
ChemSpider	8349550
UNII	O8E148Q90M
ChEMBL	ChEMBL3234035
CompTox Dashboard (EPA)	DTXSID701019168
Chemical and physical data
Formula	C₂₈H₃₆O₆
Molar mass	468.590 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCCC(C)(C)C1=CC(=C(C(=C1)OC(=O)/C=C/C(=O)O)[C@H]2CC(=O)[C@H]3C[C@@H]2C3(C)C)O
InChI InChI=1S/C28H38O6/c1-6-7-8-9-12-27(2,3)17-13-22(30)26(23(14-17)34-25(33)11-10-24(31)32)18-15-21(29)20-16-19(18)28(20,4)5/h10-11,13-14,18-20,30H,6-9,12,15-16H2,1-5H3,(H,31,32)/b11-10+/t18-,19-,20+/m0/s1 Key:GSTZHANFXAKPSE-MXTREEOPSA-N

Cannabinor

See also

References