Recent advances in the cannabinoids

Expert Opinion on Therapeutic Patents

Volumn 12, Issue 10, 2002, Pages 1475-1489

  Adam, Julia ^a   Cowley, Phillip ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Cannabinoid; Cannabinoid agonist; Cannabinoid antagonist; Cannabinoid modulator; CB1; CB2; Endocannabinoid

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; 4 [4 (1,1 DIMETHYLHEPTYL) 2,6 DIMETHOXYPHENYL] 6,6 DIMETHYLBICYCLO[3.1.1]HEPT 2 EN 2 YLMETHANOL; 5 (4 CHLORO 3 METHYLPHENYL) 1 (4 METHYLBENZYL) N (1,3,3 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YL) 3 PYRAZOLECARBOXAMIDE; 6 IODO 3 (4 METHOXYBENZOYL) 2 METHYL 1 (2 MORPHOLINOETHYL)INDOLE; AJULEMIC ACID; AM 1703; AM 2230; AM 694; ANANDAMIDE; ANTIINFECTIVE AGENT; CANNABIDIOL; CANNABIDIOL DERIVATIVE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID DERIVATIVE; CANNABINOID RECEPTOR; CANNABINOID RECEPTOR AGONIST; CANNABINOID RECEPTOR ANTAGONIST; CP 55 940; DEXANABINOL; DRONABINOL; KETONE DERIVATIVE; NABILONE; NOLADIN ETHER; RIMONABANT; TETRAHYDROCANNABINOL; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIRODHAMINE;

ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ATAXIA; BINDING AFFINITY; BRAIN INJURY; CHEMOTHERAPY INDUCED EMESIS; CLINICAL TRIAL; COGNITIVE DEFECT; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; COUGHING; DEGENERATIVE DISEASE; DRUG DELIVERY SYSTEM; DRUG INHIBITION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HUMAN; HYPOTENSION; IMMUNOPATHOLOGY; MOUSE; NEUROPATHY; NEUROPROTECTION; NONHUMAN; OBESITY; PAIN; RAT; REVIEW; SEDATION; STRUCTURE ACTIVITY RELATION; TACHYCARDIA; TRANQUILIZING ACTIVITY; XEROSTOMIA;

EID: 0036799598     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.12.10.1475     Document Type: Review

References (57)

1. GOYA P, JAGEROVIC N: Recent advances in camnabinoid receptor agonists and antagonists. Exp. Opin. Ther. Parents (2000) 10:1529-1538.
2. HOWLETT AC, BARTH F, BONNER TI et al.: International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol. Rev. (2002) 54:161-202.
3. MATSUDA LA, LOLAIT SJ, BROWNSTEIN MJ, YOUNG AC, BONNER TI: Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature (1990) 346:561-564.
4. SHIRE D, CARILLON C, KAGHAD M et al.: An amino-terminal variant of the central cannabinnoid receptor resulting from alternative splicing. J. Biol. Chem. (1995) 270:3726-3731.
5. MUNRO S, THOMAS KL, ABU SHAAR M: Molecular characterization of a peripheral receptor for cannabinoids. Nature (1993) 365:61-65.
6. DEVANE WA, HANUS L, BREUER A et al.: Isolation and structure, of a brain constituent that binds to the cannabinoid receptor. Science (1992) 258:1946-1949.
7. MECHOULAM R, BEN-SHABAT S, HANUS L et al.: Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem. Pharmacol. (1995) 50:83-90.
8. SUGIURA T, KONDO S, SUKAGAWA A et al.: 2-Arachidonylglycerol: a possible endogenous cannabinoid receptor ligand in the brain. Biochem. Biophys. Res. Commun. (1995) 215:89-97.
9. HANUS L, ABU-LAFI S, FRIDE S et al.: 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid CB1 receptor. Proc. Natl. Acad. Sci. USA (2001) 98:3662-3665.
10. PORTER AC, SAUER J-M, KNIERMAN MD et al.: Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor. J. Pharmacol. Exp. Ther. (2002) 301:1020-1024.
11. COMPTON DR, JOHNSON MR, MELVIN LS, MARTIN BR: Pharmacological profile of a series of bicyclic cannabinoid analogs: classification as cannabimimetic agents. J. Pharmacol. Exp. Ther. (1992) 260:201-209.
12. CALIGNANO A, LA RANA G, GIUFFRIDA A. PIOMELLI D: Control of pain initiation by endogenous cannabinoids. Nature (1998) 394:277-281.
13. CALIGNANO A, LA RANA G, PIOMELLI D: Antinociceptive activity of the endogenous fatty acid amide, palmitylethanolamide. Eur. J. Pharmacol. (2001) 419:191-198.
14. DI MARZO V, BREIVOGEL CS, TAO Q et al.: Levels, metabolism, and pharmacological activity of anandamide in CB1 cannabinoid receptor knockout mice. evidence for non-CB1, non-CB2 receptor-mediated actions of anandamide in mouse brain. J. Neurochem. (2000) 75:2434-2444.
15. BREIVOGEL CS, GRIFFIN G, DI MARZO V, MARTIN BR: Evidence for a new G-protein coupled cannabinoid receptor in mouse brain. Mol. Pharmacol. (2001) 60:155-163.
16. JÁRAI Z, WAGNER JA, VARGA K et al.: Cannabinoid-induced mesenteric vasodilation through an endothelial site distinct from CB1 or CB2 receptors. Proc. Natl. Acad. Sci. USA (1999) 96:14136-14142.
17. SHOHAMI E, MECHOULAM R: Dexanabinol (HU-211): a non-psychotropic cannabinoid with neuroprotective properties. Drug Dev. Res. (2000) 50:211-215.
18. MARSICANO G, MOOSMANN B, HERMANN H, LUTZ B, BEHL C: Neuroprotective properties of cannabinoids against oxidative stress:role of cannabinoid receptor CB1. J. Neurochem. (2002) 80:448-456.
19. MECHOULAM R. PANIKASHVILI D, SHOHAMI E: Cannabinoids and brain injury: therapeutic implications. Trends in Molecular Medicine (2002) 8:58-61.
20. GLASS M: The role of cannabinoids in neurodegenerative diseases. Prog. Neuropsychopharmacol. & Biol. Pychiat. (2001) 25:743-765.
21. HUFFMAN JW: The search for selective ligands for the CB2 receptor. Current Pharmaceutical Design (2000) 6:1323-1337.
22. HANUS L, BREUER A, TCHILIBON S, SHILOAH S, GOLDENBERG D et al.: HU-308:a specific agonist for CB2, a peripheral cannabinoid receptor. Proc. Natl. Acad. Sci. USA (1999) 96:14228-14233.
23. HUFFMAN JW, JOYNER HH, LEE MD, JORDAN RD, PENNINGTON WT: Synthesis of both enantiomers of nabilone from a common intermediate. Enantiodivergent synthesis of cannabinoids. J. Org. Chem. (1991) 56:2081-2086.
24. DRAKE DJ, JENSEN RS, BUSCH PETERSEN J et al.: Classical/non-classical hybrid cannabinoids:southern aliphatic chain-functionalised C-6β methyl, ethyl and propyl analogues. J. Med. Chem. (1998) 41:3596-3608.
25. GALVE-ROPERH I, SÁNCHEZ C, CORTÉS ML, GÓMEZ DEL PULGAR T, IZQUIERDO M, GUZMÁN M: Antitumoral action of cannabinoids: involvement of sustained ceramide accumulation and extracellular signal-regulated kinase activation. Nature Medicine (2000) 6:313-319.
26. DE PETROCELLIS L, MELCK D, PALMISANO A et al.: The endogenous cannabinoid anandamide inhibits human breast cancer cell proliferation. Proc. Natl. Acad. Sci. USA (1998) 95:8375-8380.
27. RECHT, LD et al.: Antitumour effects of ajulemic acid (CT-3), a synthetic non-psychoactive cannabinoid. Biochem. Pharmacol. (2001) 62:755-763.
28. MECHOULAM P, RHEE M-H, VOGEL Z et al.: Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase. J. Med. Chem. (1997) 40:3228-3233.
29. BURSTEIN, SH: The cannabinoid acids: non-psychoactive derivatives with therapeutic potential. Pharmacol. Ther. (1999) 82:87-96.
30. BISOGNO T, HANUŠ L, DE PETROCELLIS L et al.: Molecular targets for cannabidiol and its synthetic analogues: effect on vanilloid VR1 receptors and on the cellular uptake and enzymatic hydrolysis of anandamide. Br. J. Pharmacol. (2001) 134:845-852.
31. BARTH F, RINALDI-CARMONA M: The development of cannabinoid antagonists. Current Med. Chem. (1999) 6:745-755.
32. RINALDI-CARMONA M, BARTH F. HEAULME M et al.: SR141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett. (1994) 350:240-244.
33. NAKAMURA-PALACIOS EM, MOERSCHBAECHER JM, BARKER LA: The pharmacology of SR141716A. a review. CNS Drug Reviews (1999) 5:43-58.
34. RINALDI-CARMONA M, BARTH F, MILLAN J et al.: SR144528, the first potent and selective antagonist of the CB2 cannabinoid receptor. J. Pharmacol. Exp. Ther. (1998) 294:644-650.
35. LE FUR G, ARNONE M, RINALDI CARMONA M, BARTH F, HESHMATI H: SR141716A, a selective antagonist of CB1 receptors and obesity. International Cannabinoid Research Society Symposium on the Cannabinoids. San Lorenzo de El Escorial, Spain (2001).
36. HESHMATI HM, CAPLAIN H, BELLISLE F, MOSSE M, FAUVEAU C, LE FUR G: SR141716A, a selective cannabinoid CB1 receptor antagonist, reduces hunger, caloric intake and body weight in overweight or obese men. The North American Association for the study of Obesity Annual Meeting. Quebec City, Canada (2001). Suppl. 3 O69.
37. THOMAS BF, GILLIAM AF, BURCH DF, ROCHE MJ, SELTZMAN HH: Comparitive receptor binding analyses of cannabinoid agonists and antagonists. J. Pharmacol, Exp. Ther. (1998) 285:285-292.
38. WILEY JL, JEFFERSON RG, GRIER MC, MAHADEVAN A, RAZDAN RK, MARTIN BR: Novel pyrazole cannabinoids-insights into CB1 receptor recognition and activation. J. Pharmacol. Exp. Ther. (2001) 296:1013-1022.
39. FRANCISCO MEY, SELTZMAN HH, GILLIAM AF et al.: Synthesis and structure-activity relationships of amide and hydrazide analogues of the cannabinoid CB1 receptor antagonist N-(piperidinyl)-5-(4-chlorophenyl)1-(2,4-dichlrophenyl) 4-methyl-1H-pyrazole-3-carboxamide (SR141716). J. Med. Chem. (2002) 45:2708-2719.
40. OOMS F, WOUTERS J, OSCARI O et al.: Exploration of the pharmacophore of 3-alkyl-5-arylimidazolinediones as new CB1 cannabinoid receptor ligands and potential antagonists: synthesis, lipophilicity, affinity and molecular modelling. J. Med. Chem. (2002) 45:1748-1756.
41. MARTIN D, NEAR SL: Protective effect of the interleukin-1 receptor antagonist (IL-1ra) on experimental allergic enchephalomyelitis in rats. J. Neuroimmunol. (1995) 61:241-245.
42. GERRITSE K, LAMAN JD, NOELLE RJ et al.: CD40-CD40 ligand interactions in experimental allergic encephalomyelitis and multiple sclerosis. Proc. Natl. Acad. Sci. USA (1996) 93;2499-2504.
43. CORRIGALL WA, COEN KM: Nicotine maintains robust self-administration in rats on a limited-access schedule. Psychopharmacoiogy (1989) 99:473-478.
44. IWAMURA H, SUZUKI H, UEDA Y, KAYA T, INABA T: In vitro and in vivo pharmacological characterization of JTE-907, a novel selective ligand for cannabinoid CB2 receptor. J. Pharmacol. Exp. Ther. (2001) 296:420-425.
45. PIOMELLI D, GIUFFRIDA A, CALIGNANO A. RODRIGUEZ DE FONCESCA F: The endocannabinoid system as a target for therapeutic drugs. TIPS (2000) 21:218-224.
46. DI MARZO V, BISOGNO T, DE PETROCELLIS L: Endocannabinoids:new targets for drug development. Current Pharmaceutical Design (2000) 6:1361-1380.
47. DI MARZO V, DE PETROCELLIS L, BISOGNO T: Endocannabinoids Part I: molecular basis of endocannabinoid formation, action and inactivation and development of selective inhibitors. Emerging Therapeutic Targets (2001) 5:241-265.
48. DI MARZO V, BISOGNO T, DE PETROCELLIS L: Endocannabinoids Part II: pathological CNS conditions involving the endocannabinoid system and their possible treatment with endocannabinoid-based drugs. Emerging Therapeutic Targets (2001) 5:349-362.
49. DI MARZO V, MATIAS I, DE PETROCELLIS L: Endocannabinoids Part III: diseases of peripheral organs involving the endocannabinoid system and their possible treatment with endocannabinoid-based drugs. Emerging Therapeutic Targets (2002) 6:335-347.
50. WILSON RI, NICOLL RA: Endocannabinoid signalling in the brain. Science (2002) 296:678-682.
51. UEDA N, PUFFENBARGER RA, YAMAMOTO S, DEUTSCH DG: The fatty acid amide hydrolase. Chem. Phys. Lipids (2000) 108:107-121.
52. FOWLER CJ, JONSSON K-O, TIGER G: Fatty acid amide hydrolase: biochemistry, pharmacology and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonylglycerol, palmitoylethanolamide and oleamide. Biochem. Pharmacol. (2001) 62:517-526.
53. MARTIN BR, BELETSKAYA I, PATRICK G et al.: Cannabinoid properties of methylfluorophosphonate analogs. J. Pharmacol. Exp. Ther. (2000) 294:1209-1218.
54. BOGER DL, MIYAUCHI H, HEDRICK MP: α-Keto heterocycle inhibitors of fatty acid amide hydrolase:carbonyl group modification and α-substitution. Bioorg. Med. Chem. Lett. (2001) 11:1517-1520.
55. GLASER ST, STUDHOLME KM, FATADE F, YAZULLA S, ABUMRAD N, DEUTSCH DG: Is there an anandamide transporter? International Cannabinoid Research Society 12th Annual Symposium on the Cannabinoids. Pacific Grove, CA, USA (2002).
56. BELTRAMO M, STELLA N, CALIGNANO A, LIN SY, MAKRIYANNIS A, PIOMELLI D: Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science (1997) 277:1094-1097.
57. DI MARZO V, BREIVOGEL C, BISOGNO T et al.: Neurobehavioural activity in mice of N-vanillyl-arachidonyl-amide. Eur. J. Pharmacol. (2000) 406:363-374.