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RB-64

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Chemical compound Pharmaceutical compound
RB-64
Legal status
Legal status
  • Legal/Uncontrolled
Identifiers
IUPAC name
  • Methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(2-thiocyanatoacetyl)oxy-2,4a,5,6,7,8,9,10a-octahydro-1H-benzoisochromene-7-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H27NO8S
Molar mass489.54 g·mol
3D model (JSmol)
SMILES
  • C12CC3C(=O)O(C3(1C(=O)(C2C(=O)OC)OC(=O)CSC#N)C)C4=COC=C4
InChI
  • InChI=1S/C24H27NO8S/c1-23-6-4-14-22(29)33-17(13-5-7-31-10-13)9-24(14,2)20(23)19(27)16(8-15(23)21(28)30-3)32-18(26)11-34-12-25/h5,7,10,14-17,20H,4,6,8-9,11H2,1-3H3/t14-,15-,16-,17-,20-,23-,24-/m0/s1
  • Key:AZPUAKGNQXURGA-ZWLNRFIDSA-N

RB-64 is a semi-synthetic derivative of salvinorin A. It is an irreversible agonist, with a reactive thiocyanate group that forms a bond to the κ-opioid receptor (KOR), resulting in very high potency. It is functionally selective, activating G proteins more potently than β-arrestin-2. RB-64 has a bias factor of up to 96 and is analgesic with fewer of the side-effects associated with unbiased KOR agonists. The analgesia is long-lasting. Compared with unbiased agonists, RB-64 evokes considerably less receptor internalization.

See also

References

  1. Yan F, Bikbulatov RV, Mocanu V, Dicheva N, Parker CE, Wetsel WC, et al. (July 2009). "Structure-based design, synthesis, and biochemical and pharmacological characterization of novel salvinorin A analogues as active state probes of the kappa-opioid receptor". Biochemistry. 48 (29): 6898–6908. doi:10.1021/bi900605n. PMC 2752672. PMID 19555087.
  2. White KL, Scopton AP, Rives ML, Bikbulatov RV, Polepally PR, Brown PJ, et al. (January 2014). "Identification of novel functionally selective κ-opioid receptor scaffolds". Molecular Pharmacology. 85 (1): 83–90. doi:10.1124/mol.113.089649. PMC 3868907. PMID 24113749.
  3. White KL, Robinson JE, Zhu H, DiBerto JF, Polepally PR, Zjawiony JK, et al. (January 2015). "The G protein-biased κ-opioid receptor agonist RB-64 is analgesic with a unique spectrum of activities in vivo". The Journal of Pharmacology and Experimental Therapeutics. 352 (1): 98–109. doi:10.1124/jpet.114.216820. PMC 4279099. PMID 25320048.
Opioid receptor modulators
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
  • Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)


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