LBP-1 (drug)

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]

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

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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