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Cannabinor

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Chemical compound Pharmaceutical compound
Cannabinor
Identifiers
IUPAC name
  • (E)-4-heptanyl]-3-hydroxy-5-(2-methyloctan-2-yl)phenoxy]-4-oxobut-2-enoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H36O6
Molar mass468.590 g·mol
3D model (JSmol)
SMILES
  • CCCCCCC(C)(C)C1=CC(=C(C(=C1)OC(=O)/C=C/C(=O)O)2CC(=O)3C2C3(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. 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. 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.

See also

References

  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.
Cannabinoids
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
Allosteric CBRTooltip Cannabinoid receptor ligands
Endocannabinoid
enhancers
(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)


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