LBP-1 (drug)

LBP-1
Identifiers
IUPAC name
  • 2-{4-[(3-[7-chloro-1-(oxan-4-ylmethyl)indol-3-yl]-1,2,4-oxadiazol-5-yl)methyl]piperazin-1-yl}acetamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H29ClN6O3
Molar mass472.97 g·mol−1
3D model (JSmol)
SMILES
  • ClC1=C(N(CC2CCOCC2)C=C3C4=NOC(CN5CCN(CC(N)=O)CC5)=N4)C3=CC=C1
InChI
  • InChI=1S/C23H29ClN6O3/c24-19-3-1-2-17-18(13-30(22(17)19)12-16-4-10-32-11-5-16)23-26-21(33-27-23)15-29-8-6-28(7-9-29)14-20(25)31/h1-3,13,16H,4-12,14-15H2,(H2,25,31)
  • Key:AKWUNZFZIXEOPV-UHFFFAOYSA-N

LBP-1 is a drug originally developed by Organon for the treatment of neuropathic pain,[1][2][3] It acts as a potent and selective cannabinoid receptor agonist, with high potency at both the CB1 and CB2 receptors, but low penetration of the blood–brain barrier. This makes LBP-1 peripherally selective, and while it was effective in animal models of neuropathic pain and allodynia, it did not produce cannabinoid-appropriate responding suggestive of central effects, at any dose tested.[4]

See also

References

  1. ↑ Morrison AJ, Adam JM, Baker JA, Campbell RA, Clark JK, Cottney JE, et al. (January 2011). "Design, synthesis, and structure-activity relationships of indole-3-heterocycles as agonists of the CB1 receptor". Bioorganic & Medicinal Chemistry Letters. 21 (1): 506–9. doi:10.1016/j.bmcl.2010.10.093. PMID 21075630.
  2. ↑ Kiyoi T, Adam JM, Clark JK, Davies K, Easson AM, Edwards D, et al. (March 2011). "Discovery of potent and orally bioavailable heterocycle-based cannabinoid CB1 receptor agonists". Bioorganic & Medicinal Chemistry Letters. 21 (6): 1748–53. doi:10.1016/j.bmcl.2011.01.082. PMID 21316962.
  3. ↑ Ratcliffe P, Adam JM, Baker J, Bursi R, Campbell R, Clark JK, et al. (April 2011). "Design, synthesis and structure-activity relationships of (indo-3-yl) heterocyclic derivatives as agonists of the CB1 receptor. Discovery of a clinical candidate". Bioorganic & Medicinal Chemistry Letters. 21 (8): 2541–6. doi:10.1016/j.bmcl.2011.02.023. PMID 21411321.
  4. ↑ Adam JM, Clark JK, Davies K, Everett K, Fields R, Francis S, et al. (April 2012). "Low brain penetrant CB1 receptor agonists for the treatment of neuropathic pain". Bioorganic & Medicinal Chemistry Letters. 22 (8): 2932–7. doi:10.1016/j.bmcl.2012.02.048. PMID 22421020.
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