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Cannabinor

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Cannabinor
Identifiers
  • (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
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC28H36O6
Molar mass468.590 g·mol−1
3D model (JSmol)
  • 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=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 selectivecannabinoidCB2receptoragonist.[1][2] It is classed as a "nonclassical" cannabinoid with a chemical structure similar to that ofcannabidiol. It has a CB2 affinity of 17.4 nM vs 5,585 nM at CB1, giving it over 300× selectivity for CB2.[3] It showedanalgesic effects in animal studies especially in models ofneuropathic pain, but failed in Phase IIb humanclinical trials due to lack of efficacy.[4]

See also

[edit]

References

[edit]
  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.
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
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers
(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)


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