Monoamine oxidase inhibitors

Expert Opinion on Therapeutic Patents

Volumn 12, Issue 12, 2002, Pages 1813-1829

  Keung, Wing Ming ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

Author keywords

Affective disorders; Aliphatic propargylamines; Alzheimer's disease; Amidines; Aminoindans; Amyotropic lateral sclerosis; Anxiety; Attention deficit and hyperactivity disorder (ADHD); Befloxatone; Cardiovascular diseases; Dementia; Depression; Dopamine; Drug dependence; Epilepsy; Huntington's chorea; Indoles; Lofepramine; Moclobemide; Multiple sclerosis; Obesity; Obessixve compulsive disorder; Parkinson's disease; Phenelzine; Phenylethylamine; Phenyloxazolidinones; Post traumatic stress disorders; Selegiline; Serotonin; Tetrahydroisoquinolines; Tricyclic heterocyclics; Tyramine

Indexed keywords

ALIPHATIC COMPOUND; AMINE OXIDASE (FLAVIN CONTAINING); BEFLOXATONE; BROFAROMINE; CHOLINESTERASE; CLORGYLINE; DEOXYVASICINE; HARMINE; HYDRAZINE DERIVATIVE; HYPOXANTHINE DERIVATIVE; INDAN DERIVATIVE; INDOLE DERIVATIVE; IPRONIAZID; ISOCARBOXAZID; ISONIAZID; MOCLOBEMIDE; MONOAMINE OXIDASE A INHIBITOR; MONOAMINE OXIDASE B INHIBITOR; MONOAMINE OXIDASE INHIBITOR; NIALAMIDE; OXAZOLIDINONE DERIVATIVE; PARGYLINE; PHENELZINE; PHENETHYLAMINE DERIVATIVE; PRODRUG; SELEGILINE; TETRAHYDROISOQUINOLINE DERIVATIVE; TRANYLCYPROMINE; TRICYCLIC ANTIDEPRESSANT AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

DEPRESSION; DRUG CLASSIFICATION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG FORMULATION; DRUG HALF LIFE; DRUG MANUFACTURE; DRUG UTILIZATION; HEPATITIS; HUMAN; NEUROLOGIC DISEASE; NONHUMAN; PATENT; PHARMACOPHORE; REVIEW;

EID: 0036931928     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.12.12.1813     Document Type: Review

References (76)

1. SHIH JC, CHEN K, RIDD MJ: Monoamine oxidase: from genes to behavior. Annu. Rev. Neurosci. (1999) 22:197-217.
2. ABELL CW, KWAN SW: Molecular characterization of monoamine oxidases A and B. Prog. Nucleic Acid Res. Mol. Biol. (2001) 65:129-156.
3. BENEDETTI MS: Biotransformation of xenobiotics by amine oxidases. Fundam. Clin. Pharmacol. (2001) 15:75-84.
4. KALGUTKAR AS, DALVIE DK, CASTAGNOLI N Jr et al.: Interactions of nitrogen-containing xenobiotics with monoamine oxidase (MAO) isozymes A and B: SAR studies on MAO substrates and inhibitors. Chem. Res. Toxicol. (2001) 14:1139-1162.
5. BACH AW, LAN NC, JOHNSON DL et al.: cDNA cloning of human liver monoamine oxidase A and B: molecular basis of differences in enzymatic properties. Proc. Natl. Acad. Sci. USA (1988) 85:4934-4938.
6. LAN NC, CHEN CH, SHIH JC: Expression of functional human monoamine oxidase A and B cDNAs in mammalian cells. J. Neurochem. (1989) 52:1652-1654.
7. JOHNSTON JP: Some observations upon a new inhibitor of monoamine oxidase in brain tissue. Biochem. Pharmacol. (1968) 17:1285-1297.
8. FOWLER CJ, ORELAND L, CALLINGHAM BA: The acetylenic monoamine oxidase inhibitors clorgyline, deprenyl, pargyline and J-508: their properties and applications. Pharm. Pharmacol. (1981) 33:341-347.
9. KNOLL J, MAGYAR K: Some puzzling pharmacological effects of monoamine oxidase inhibitors. Adv. Biochem. Pychopharmacol. (1972) 5:393-408.
10. CHEN K, SHIH J: Monoamine oxidase type A and B: structure, function and behaviour. Adv. Pharmacol. (1998) 42:292-296.
11. TIPTON KF, O'CARROLL AM, McCRODDEN JM: The catalytic behavior of monoamine oxidase. J. Neural Transm. (1987) 23S:25-35.
12. CASES O, SEIF I, GRIMSBY J et al.: Aggressive behavior and altered amounts of brain serotonin and norepinephrine in mice lacking MAO A. Science (1995) 268:1763-1766.
13. KIM JJ, SHIH JC, CHEN K et al.: Selective enhancement of emotional, but nor motor, learning in monoamine oxidase A-deficient mice. Proc. Natl. Acad. Sci. USA (1997) 94:5929-5933.
14. GRIMSBY J, TOTH M, CHEN K et al.: Increased stress response and β-phenylethylamine in MAO-B deficient mice. Nat. Genet. (1997) 17:1-5.
15. SQUIRES RF: Multiple forms of monoamine oxidase in intact mitochondria as characterized by selective inhibitors and thermal stability: a comparison of eight mammalian species. Adv. Biochem. Pharmacol. (1972) 5:355-369.
16. GARRICK NA, MURPHY DL: Species differences in the deamination of dopamine and other substrates for monoamine oxidase in brain. Pychopharmacology (1980) 72:27-33.
17. KRUEGER MG, MAZOUZ F, RAMSAY RR et al.: Dramatic species differences in the susceptibility of monoamine oxidase B to a group of powerful inhibitors. Biochem. Biophys. Res. Commun. (1995) 206:556-562.
18. O'BRIEN E, DOSTERT P, TIPTON KF: Species differences in the interactions of anticonvulsants milacemide and some analogs with monoamine oxidase B. Biochem. Pharmacol. (1995) 50:317-324.
19. BINDA C, NEWTON-VINSON P, HUBALEK F et al.: Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Nat. Struct. Biol. (2002) 9:22-26.
20. MABIC S, CASTAGNOLI N Jr: Assessment of structural requirements for the monoamine oxidase-B-catalyzed oxidation of 1,4-disubstituted-1,2,3,6-tetrahydropyridine derivatives related to the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Med. Chem. (1996) 39:3694-3700.
21. NANDIGAMA RK, EDMONDSON DE: Structure-activity relations in the oxidation of phenylethylamine analogues by recombinant human liver monoamine oxidase A. Biochemistry (2000) 39:15258-15265.
22. MILLER JR, EDMONDSON DE: Structure-activity relationships in the oxidation of para-substituted benzylamine analogues by recombinant human liver monoamine oxidase A. Biocehmistry (1999) 38:13670-13683.
23. ROBITZEK EH, SELIKOFF IJ, ORNSTEIN GG: Chemotherapy of human tuberculosis with hydrazine derivatives of isonicotinic acid. Q. Bull. Sea View Hosp. (1952) 13:27-51.
24. ZELLER EA, BARDSKY J: In vivo inhibition of liver and brain monoamine oxidase by 1-isonicotinyl-2-isopropyl-hydrazine. Proc. Soc. Exp. Biol. (1952) 81:459-461.
25. O'CONNOR JB, HOWLETT KS, WAGNER RR. Side effects accompanying use of iproniazid. Am. Rev. Tuberc. (1953) 68:270-272.
26. LOOMER HP, SAUNDERS JC, KLINE NS: A clinical and pharmacodynamic evaluation of iproniazid as a psychic energizer. Am. Pychiatr. Assoc. Psychiatric Res. Rep. (1957) 8:129-141.
27. KLINE NS: Monoamine oxidase inhibitors: An unfinished picaresque tale. In: Discoveries in Biological Psychiatry Ayd FJ, Blackwell B (Eds), Lippincott, Philadelphia, USA (1970):194-204.
28. MEDICAL RESEARCH COUNCIL: Clinical trial of the treatment of depressive illness. Br. Med. J. (1965) 251:881-886.
29. KLEIN DF, GITTELMAN R, QUITKIN F et al.: Diagnosis and treatment of psychiatric disorders: adults and children, 2nd Ed., Williams & Wilkins, Baltimore (1980).
30. WEST ED, DALLY P: Effects of iproniazid on depressive syndromes. Br. Med. J. (1959) 1:1491-1494.
31. ROBINSON DS, NIES A, RAVARIS CL et al.: The monoamine oxidase inhibitor, phenelzine, in the treatment of depressive-anxiety states. Arch. Gen. Pychiat. (1973) 29:407-413.
32. PARE CMB: The present status of monoamine oxidase inhibitors. Br. J. Pychiat. (1985) 146:576-584.
33. QUITKIN FM, RIFKIN A, KLEIN DF: Monoamine oxidase inhibitors: a review of antidepressant effectiveness. Arch. Gen. Pychiat. (1979) 36:749-760.
34. LOTUFO-NETO F, TRIVEDI M, THASE M: Meta-analysis of the reversible inhibitors of monoamine oxidase type A moclobemide and brofaromine for the treatment of depression. Neuropychopharmacology (1999) 20:226-247.
35. CALNE DB: Drug therapy: treatment of Parkinson's disease. N. Engl. J. Med. (1993) 329:1021-1027.
36. ZHAO Z, DALVIE D, NAIMAN N et al.: Design, synthesis, and biological evaluation of novel 4-subsituted 1-methyl-1,2,3,6-tetrahydropyridine analogs of MPTP. J. Med. Chem. (1992) 35:4473-4478.
37. KALGUTKAR AS, CASTAGNOLI N Jr, TESTA B: Selective inhibitors of monoamine oxidase (MAO-A and MAO-B) as probes of its catalytic site and mechanism. Med. Res. Pev. (1995) 15:325-388.
38. WALSH BT, STEWART JW, ROOSE SP et al.: Treatment of bulimia with phenelzine. Arch. of Gen. Psychiat. (1984) 41:1105-1109.
39. DAVIDSON J, RAFT D: Monoamine oxidase inhibitors in patients with chronic pain. Arch. Gen. Psychiat. (1985) 42:635-636.
40. JENIKE MA, SURMAN OS, CASSEM NH et al.: Monoamine oxidase inhibitors in obsessive compulsive disorder. J. Clin. Psychiat. (1983) 44:131-132.
41. ZAMETKIN A, RAPOPORT JL, MURPHY DL et al.: Treatment of hyperactive children with monoamine oxidase inhibitors. Arch. Gen. Psychiat. (1985) 42:962-977.
42. PAUL H, WENDER MD: Pharmacotherapy of attention-deficit/hyperactivity disorder in adults. J. Clin. Psychiat. (1998) 59:76S-79S.
43. WYATT RJ, POTKIN SJ, MURPHY DL: Platelet monoamine oxidase activity in schizophrenia: a review of the data. Am. J. Psychiat. (1979) 136:377-385.
44. YU PH, BOWEN RC, DAVIS BA et al.: Platelet monoamine oxidase activity and trace acid levels in plasma of agoraphobic patients. Acta Psychiat. Scand. (1983) 78:188-194.
45. VON KNORRING AL, ORELAND L, WINBLAD B: Personality traits related to monoamine oxidase (MAO) activity in platelets. Psychiat. Res. (1984) 12:11-26.
46. VON KNORRING AL, HALLMAN J, VON KNORRING L et al.: Platelet monoamine oxidase activity in type 1 and type 2 alcoholism. Alcohol Alcohol. (1991) 26:409-416.
47. COURSEY RD, BUCHSBAUM MS, MURPHY DL: Platelet MAO activity and evoked potentials in the identification of subjects biologically at risk for psychiatric disorders. Br. J. Psychiat. (1979) 134:372-381.
48. SIMS KB, DE LA CHAPELLE A, NORIO R et al.: Monoamine oxidase deficiency in males with an X chromosome deletion. Neurons (1989) 2:1069-1076.
49. FORD MF: Treatment of depression in Huntington's disease with monoamine oxidase inhibitors. Brit. J. Psychiat. (1986) 149:654-656.
50. MARKIANOS M, SFAGOS C, BISTOLAKI E: Platelet monoamine oxidase and plasma dopamine-beta-hydroxylase activities in patients with multiple sclerosis. Acta Neuro. Scand. (1991) 84:531-533.
51. MAZZINI L, TESTA D, BALZARINI C et al.: An open-randomized clinical trial of selegiline in amyotrophic lateral sclerosis. J. Neurol. (1994) 241:223-227.
52. MYLLYLA VV, SOTNIEMI KA, VUORINEN JA et al.: Selegiline as initial treatment in de novo Parkinsonian patients. Neurology (1992) 42:339-343.
53. TARIOT PN, COHEN R, SUNDERLAND T et al.: L-Deprenyl in Alzheimer's disease. Arch. Gen. Psychiat. (1987) 44:427-433.
54. TARIOT PN, SUNDERLAND T, WEINGARTNER H et al.: Cognitive effects of L-Deprenyl in Alzheimer's disease. Psychopharmacology (1987) 91:489-495.
55. KUHN W. MULLER TH: The clinical potential of deprenyl in neurological and psychiatric disorders. J. Neural Transm. (1996) 48:85-93.
56. EBADI M: Therapeutic potential of selegiline in Parkinson's disease and other neurological disorders. In: Recent advances in neurodegenerative disorders. Marwah J, Teitelbaum H (Eds), Prominent Press, Scottsdale, AZ (1998):256-350.
57. KIM H, SABLIN SO, RAMSAY RR: Inhibition of monoamine oxidase A by β-carboline derivatives. Arch. Biochem. Biophys. (1997) 337:137-142.
58. MEDVEDEV AE, GOODWIN B, CLOW A et al.: Inhibitory potency of some isatin analogues on human monoamine oxidase A and B. Biochem. Pharmacol. (1992) 44:590-592.
59. FINK DM, PALERMO MG, BORES GM et al.: Imino 1,2,3,4-tetrahydrocyclopent[B]indole carbamates as dual inhibitors of acetylcholinesterase and monoamine oxidase. Bioorg. Med. Chem. Lett. (1996) 6:625-630.
60. HARFENIST M, McGEE, DPC, WHITE HL: A selective, reversible, competitive inhibitor of monoamine oxidase A containing no nitrogen with negligible potential of tyramine induced blood pressure rise. J. Med. Chem. (1991) 34:2931-2933.
61. HARFENIST M, JOYNER CT, MIZE PD et al.: Selective inhibitors of monoamine oxidase 2 Arylamide SAR. J. Med. Chem. (1994) 37:2085-2089.
62. HARFENIST M, McGEE DPC, REEVES MD et al.: Selective inhibitors of monoamine oxidase (MAO). 5. 1-substituted phenoxathiin inhibitors containing no nitrogen that inhibit MAO A by binding it to a hydrophobic site. J. Med. Chem. (1998) 41:2118-2125.
63. TIPTON KF, MCCRODDEN JM, KALIR AS et al.: Inhibition of rat liver monoamine oxidase by alpha-methyl- and N-propargyl-amine derivatives. Biochem. Pharmacol. (1982) 31:1251-1255.
64. ULUS IH, MAHER TJ, WURTMAN RJ: Characterization of phentermine and related compounds as monoamine oxidase (MAO) inhibitors. Biochem. Pharmacol. (2000) 59:1611-1621.
65. KINEMUCHI H, ARAI Y, TOYOSHIMA Y et al.: Studies on 5-fluoro-α-methyltryptamine and p-chloro-β-methylhphenylethylamine. Determination of the MAO-A and MAO-B selective inhibition in vitro. Jpn. J. Pharmacol. (1988) 46:197-199.
66. JEGHAM S, GEORGE P: Monoamine oxidase A and B inhibitors. Exp. Opin. Ther. Patents (1998) 8(9):1143-1150.
67. MARUYAMA W, YAMAMOTO T, KITANI K et al.: Mechanism underlying anti-apoptotic activity of a (-)deprenyl-related propargylamine, rasagiline. Mech. Ageing Dev. (2000) 116:181-191.
68. WEINSTOCK M, GOREN T, YOUDIM MBH: Development of a novel neuroprotective drug (TV3326) for the treatment of Alzheimer's disease, with cholinesterase and monoamine oxidase inhibitory activities. Drug Dev. Res. (2000) 50:216-222.
69. WEINSTOCK M, POLTYREV T, BEJAR C et al.: Effect of TV3326, a novel monoamine-oxidase cholinesterase inhibitor, in rat models of anxiety and depression. Psychopharmacology (2002) 160:318-324.
70. BOULTON AA: Symptomatic and neuroprotective properties of the aliphatic propargylamines. Mech. Ageing Dev. (1999) 111:201-209.
71. CLEMETT D, MARKHAM A: Linezolid. Drugs (2000) 59:815-827.
72. THULL U, KNEUBUHLER S, GAILLARD P et al.: Inhibition of monoamine oxidase by isoquinoline derivatives. Biochem. Pharmacol, (1995) 50:869-877.
73. NAOI M, NAGATSU T: Quinoline and quinaldine as naturally occurring inhibitors specific for type A monoamine oxidase. Life Sci. (1987) 40:1075-1082.
74. BEMBENEK ME, ABELL CW, CHRISEY LA et al.: Inhibition of monomine oxidases A and B by simple isoquinoline alkaloids: racemic and optically active 1,2,3,4-tetrahydro-, 3,4-dihydro-, and fully aromatic isoquinolines. J. Med. Chem. (1990) 33:147-152.
75. AZIZ SA, KNOWLES CO: Inhibition of monoamine oxidase by the pesticide chlordimeform and related compounds. Nature (1973) 242:417-418.
76. 3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors. Naunyn Schmiedebergs Arch. Pharmacol. (2001) 363:429-438.