lenabasum   Click here for help

GtoPdb Ligand ID: 9772

Synonyms: ajulemic acid | CPL-7075 | CPL7075 | CT-3 | IP-751 | IP751
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Lenabasum (ajulemic acid) is a synthetic derivative of the non-psychoactive cannabinoid THC metabolite 11-nor-9-Carboxy-THC (PubChem CID 108207) [10]. It is a non-selective cannabinoid receptor agonist [5,7]. Lenabasum exhibits potentially useful analgesic and anti-inflammatory actions [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 66.76
Molecular weight 400.26
XLogP 6.96
No. Lipinski's rules broken 1
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Canonical SMILES CCCCCCC(c1cc(O)c2c(c1)OC(C1C2CC(=CC1)C(=O)O)(C)C)(C)C
Isomeric SMILES CCCCCCC(c1cc(O)c2c(c1)OC([C@H]1[C@H]2CC(=CC1)C(=O)O)(C)C)(C)C
InChI InChI=1S/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10,14-15,18-19,26H,6-9,11-13H2,1-5H3,(H,27,28)/t18-,19-/m1/s1
1. Burstein S. (2005)
Ajulemic acid (IP-751): synthesis, proof of principle, toxicity studies, and clinical trials.
AAPS J, 7 (1): E143-8. [PMID:16146336]
2. Burstein SH. (2018)
Ajulemic acid: potential treatment for chronic inflammation.
Pharmacol Res Perspect, 6 (2): e00394. [PMID:29638269]
3. Burstein SH, Karst M, Schneider U, Zurier RB. (2004)
Ajulemic acid: A novel cannabinoid produces analgesia without a "high".
Life Sci, 75 (12): 1513-22. [PMID:15240185]
4. Chmiel JF, Flume P, Downey DG, Dozor AJ, Colombo C, Mazurek H, Sapiejka E, Rachel M, Constantine S, Conley B et al.. (2020)
Safety and efficacy of lenabasum in a phase 2 randomized, placebo-controlled trial in adults with cystic fibrosis.
J Cyst Fibros, [Epub ahead of print]. DOI: 10.1016/j.jcf.2020.09.008 [PMID:33011099]
5. Han S, Thatte J, Buzard DJ, Jones RM. (2013)
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
J Med Chem, 56 (21): 8224-56. [PMID:23865723]
6. Karst M, Salim K, Burstein S, Conrad I, Hoy L, Schneider U. (2003)
Analgesic effect of the synthetic cannabinoid CT-3 on chronic neuropathic pain: a randomized controlled trial.
JAMA, 290 (13): 1757-62. [PMID:14519710]
7. Rhee MH, Vogel Z, Barg J, Bayewitch M, Levy R, Hanus L, Breuer A, Mechoulam R. (1997)
Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase.
J Med Chem, 40 (20): 3228-33. [PMID:9379442]
8. Spiera R, Hummers L, Chung L, Frech TM, Domsic R, Hsu V, Furst DE, Gordon J, Mayes M, Simms R et al.. (2020)
Safety and Efficacy of Lenabasum in a Phase II, Randomized, Placebo-Controlled Trial in Adults With Systemic Sclerosis.
Arthritis Rheumatol, 72 (8): 1350-1360. [PMID:32336038]
9. Sumariwalla PF, Gallily R, Tchilibon S, Fride E, Mechoulam R, Feldmann M. (2004)
A novel synthetic, nonpsychoactive cannabinoid acid (HU-320) with antiinflammatory properties in murine collagen-induced arthritis.
Arthritis Rheum, 50 (3): 985-98. [PMID:15022343]
10. Vann RE, Cook CD, Martin BR, Wiley JL. (2007)
Cannabimimetic properties of ajulemic acid.
J Pharmacol Exp Ther, 320 (2): 678-86. [PMID:17105826]