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	1050478-18-6 ;
PubChem CID	25006676;
ChemSpider	28530409;
UNII	505K9LJ4MX;
CompTox Dashboard (EPA)	DTXSID50648411 ;
Chemical and physical data
Formula	C23H29ClN6O3
Molar mass	472.97 g·mol−1
3D model (JSmol)	Interactive image;
	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]

References

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.
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.
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.
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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[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.

LBP-1 (drug)

See also

References