Newer N-phthaloyl GABA derivatives with antiallodynic and antihyperalgesic activities in both sciatic nerve and spinal nerve ligation models of neuropathic pain

Pharmacology

Volumn 81, Issue 1, 2007, Pages 21-31

  Yogeeswari, Perumal ^a   Ragavendran, Jegadeesan Vaigunda ^a   Sriram, Dharmarajan ^a   Kavya, Ramkumar ^a   Vanitha, Kaliappan ^a   Neelakantan, Harshini ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

Allodynia; GABA; Hyperalgesia; Neuropathic pain; Peripheral nerve injury; Writhing response

Indexed keywords

4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL) N (3 FLUOROPHENYL)BUTANAMIDE; 4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL) N (4 METHYLPHENYL)BUTANAMIDE; 4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL) N [2 (TRIFLUOROMETHYL)PHENYL]BUTANAMIDE; 4 AMINOBUTYRIC ACID DERIVATIVE; ACETIC ACID; ACETYLSALICYLIC ACID; CARBAMAZEPINE; GABAPENTIN; JVP 1; JVP 10; JVP 2; JVP 3; JVP 4; JVP 5; JVP 6; JVP 7; JVP 8; JVP 9; LAMOTRIGINE; N (2 BROMOPHENYL) 4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)BUTANAMIDE; N (2,4 DIMETHYLPHENYL) 4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)BUTANAMIDE; N (2,5 DIMETHYLPHENYL) 4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)BUTANAMIDE; N (2,6 DIMETHYLPHENYL) 4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)BUTANAMIDE; N (3 CHLORO 2 METHYLPHENYL) 4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)BUTANAMIDE; N (4 BROMO 3 METHYLPHENYL) 4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)BUTANAMIDE; N (4 CHLOROPHENYL) 4 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)BUTANAMIDE; UNCLASSIFIED DRUG;

ACUTE DISEASE; ALLODYNIA; ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHRONIC DISEASE; CONTROLLED STUDY; DISEASE MODEL; DRUG EFFICACY; DRUG SCREENING; DRUG STRUCTURE; FEMALE; HYPERALGESIA; MALE; NERVE COMPRESSION; NERVE LIGATION; NEUROPATHIC PAIN; NONHUMAN; PRIORITY JOURNAL; RAT; SCIATIC NERVE; SPINAL NERVE; TISSUE INJURY; WRITHING TEST;

ANALGESICS; ANIMALS; DISEASE MODELS, ANIMAL; FEMALE; GAMMA-AMINOBUTYRIC ACID; HYPERALGESIA; MALE; MICE; MOLECULAR STRUCTURE; NEURALGIA; PAIN MEASUREMENT; PHTHALIMIDES; RATS; RATS, WISTAR; SCIATIC NERVE; SPINAL NERVES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 36248992805     PISSN: 00317012     EISSN: None     Source Type: Journal    
DOI: 10.1159/000107711     Document Type: Article

References (39)

1. Merskey H, Bogduk N (eds): Classification of Chronic Pain: Descriptions of Chronic Pain Syndromes and Definitions of Pain Terms. International Association for the Study of Pain Task Force on Taxonomy, 1994.
2. McQuay HJ, Tramer M, Nye BA, Carroll D, Wiffen PJ, Moore RA: A systematic review of antidepressants in neuropathic pain. Pain 1996;68:217-227.
3. Sindrup SH, Jensen TS: Efficacy of pharmacological treatments of neuropathic pain: an update and effect related to mechanism of drug action. Pain 1999;83:389-400.
4. Laughlin TM, Tram KV, Wilcox GL, Birnbaum AK: Comparison of antiepileptic drugs tiagabine, lamotrigine, and gabapentin in mouse models of acute, prolonged, and chronic nociception. J Pharmacol Exp Ther 2002;302:1168-1175.
5. Sivilotti L, Nistri A: GABA receptor mechanisms in the central nervous system. Prog Neurobiol 1991;36:35-92.
6. Meldrum BS: Epilepsy and gamma-aminobutyric acid mediated inhibition. Int Rev Neurobiol 1975;17:1-36.
7. Bartholini G, Bossi L, Lloyd KG, Morselli PL (eds): Epilepsy and GABA Receptor Agonists: Basic and Therapeutic Research (LERS monograph series). New York, Raven Press, 1985, pp 109-119.
8. Krogsgaard-Larsen P, Scheel-Kruger J, Kofoed H (eds): GABA-Neurotransmitters: Pharmacochemical Biochemical and Pharmacological Aspects. Copenhagen, Munksgaard, 1978, pp 17-27.
9. Franek M, Vaculin S, Rokyta R: GABA B receptor agonist baclofen has non-specific antinociceptive effect in the model of peripheral neuropathy in the rat. Physiol Res 2004;53:351-355.
10. Hunter JC, Gogas KR, Hedley LR, Jacobson LO, Kassotakis L, Thompson J, Fontana DJ: The effect of novel anti-epileptic drugs in rat experimental models of acute and chronic pain. Eur J Pharmacol 1997;324:153-160.
11. Field MJ, McCleary S, Hughes J, Singh L: Gabapentin and pregabalin, but not morphine and amitriptyline, block both static and dynamic components of mechanical allodynia induced by streptozocin in the rat. Pain 1999;80:391-398.
12. Devor M: Sodium channels and mechanisms of neuropathic pain. J Pain 2006;7:S3-S12.
13. Vamecq J, Bac P, Herrenknecht C, Maurois P, Delcourt P, Stables JP: Synthesis and anticonvulsant and neurotoxic properties of substituted N-phenyl derivatives of the phthalimide pharmacophore. J Med Chem 2000;43:1311-1319.
14. Ragavendran JV, Sriram D, Patel SK, Reddy IV, Bharathwajan N, Stables J, Yogeeswari P: Design and synthesis of anticonvulsants from a combined phthalimide-GABA-anilide and hydrazone pharmacophore. Eur J Med Chem 2007;in press.
15. Siegmund EA, Cadmus RA: A method for evaluating both nonnarcotic and narcotic analgesics. Proc Soc Exp Biol 1957;95:729-731.
16. Bennett GJ, Xie YK: A peripheral mononeuropathy in rat that produces disorders of pain sensation like those seen in man. Pain 1988;33:87-107.
17. Obara I, Mika J, Schafer MKH, Przewlocka B: Antagonists of the j-opioid receptor enhance allodynia in rats and mice after sciatic nerve ligation. Br J Pharmacol 2003;140:538-545.
18. Kim S, Chung JM: An experimental model for peripheral neuropathy produced by segmental spinal nerve ligation in the rat. Pain 1992;50:355-363.
19. Choi Y, Yoon YW, Na HS, Kim SH, Chung JM: Behavioral signs of ongoing pain and cold allodynia in a rat model of neuropathic pain. Pain 1994;59:369-376.
20. Field MJ, Bramwell S, Hughes J, Singh L: Detection of static and dynamic components of mechanical allodynia in rat models of neuropathic pain: are they signalled by distinct primary sensory neurones? Pain 1999;83:303-311.
21. Caudle RM, Mannes AJ, Benoliel R, Eliav E, Iadarola MJ: Intrathecally administered cholera toxin blocks allodynia and hyperalgesia in persistent pain models. J Pain 2001;2:118-127.
22. Gonzalez MI, Field MJ, Hughes J, Singh L: Evaluation of selective NK1 receptor antagonist CI-1021 in animal models of inflammatory and neuropathic pain. J Pharmacol Exp Ther 2000;294:444-450.
23. Chakraborty A, Devi RKB, Rita S, Sharatchandra KH, Singh THI: Preliminary studies on anti-inflammatory and analgesic activities of Spilanthes acmella in experimental animal models. Indian J Pharmacol 2004;36:148-150.
24. Eaton MJ, Martinez MA, Karmally S: A single intrathecal injection of GABA permanently reverses neuropathic pain after nerve injury. Brain Res 1999;835:334-339.
25. Ibuki T, Hama AT, Wang XT, Pappas GD, Sagen J: Loss of GABA immunoreactivity in the spinal dorsal horn of rats with peripheral nerve injury and promotion of recovery by adrenal medullary grafts. Neuroscience 1997;76:845-858.
26. Yaksh TL: Behavioral and autonomic correlates of the tactile evoked allodynia produced by spinal glycine inhibition: effects of modulatory receptor systems and excitatory amino acid antagonist. Pain 1989;37:111-123.
27. Smith GD, Harrison SM, Birch PJ, Elliott PJ, Malcangio M, Bowery NG: Increased sensitivity to the antinociceptive activity of (±)-baclofen in an animal model of chronic neuropathic, but not chronic inflammatory hyperalgesia. Neuropharmacol 1994;33:1103-1108.
28. Hwang JH, Yaksh TL: The effect of spinal GABA receptor agonists on tactile allodynia in a surgically-induced neuropathic pain model in the rat. Pain 1997;70:15-22.
29. Alves ND, De Castro-Costa CM, De Carvalho AM, Santos FJC, Silveira DG: Possible analgesic effect of vigabatrin in animal experimental chronic neuropathic pain. Arq Neuropsiquiatr 1999;57:916-920.
30. Brochu RM, Dick IE, Tarpley JW, Mcgowan E, Gunner D, Herrington J, Shao PP, Ok D, Li C, Parsons WH, Stump GL, Regan CP, Lynch JJ, Lyons KA, Mcmanus OB, Clark S, Ali Z, Kaczorowski GJ, Martin WJ, Priest BT: Block of peripheral nerve sodium channels selectively inhibits features of neuropathic pain in rats. Mol Pharmacol 2006;69:823-832.
31. Ilyin VI, Pomonis JD, Whiteside GT: Pharmacology of 2-[4-(4-chloro-2- fluorophenoxy) phenyl]-pyrimidine-4-carboxamide: a potent, broad-spectrum state-dependent sodium channel blocker for treating pain states. J Pharmacol Exp Ther 2006;318:1083-1093.
32. Patel MK, Ko SH, Jochnowitz N: Reversal of neuropathic pain by α-hydroxyphenylamide: a novel sodium channel antagonist. Neuropharmacology 2006;50:865-873.
33. Akada Y, Ogawa S, Amano K: Potent analgesic effects of a putative sodium channel blocker M58373 on formalin-induced and neuropathic pain in rats. Eur J Pharmacol 2006;536:248-255.
34. Yang J, Gharagozloo P, Yao J: 3-(4-Phenoxyphenyl)pyrazoles: a novel class of sodium channel blockers. J Med Chem 2004;47:1547-1552.
35. Bailleux V, Vallée L, Nuyts JP, Vamecq J: Anticonvulsant activity of some 4-amino-Nphenylphthalimides and N-(3-amino-2-met hylphenyl)phthalimides. Biomed Pharmacother 1994;48:95-101.
36. Bailleux V, Vallée L, Nuyts JP, Vamecq J: Synthesis and anticonvulsant activity of some N-phenylphthalimides. Chem Pharm Bull 1994;42:1817-1821.
37. Bailleux V, Vallée L, Nuyts JP, Hamoir G, Poupaert JH, Stables JP, Vamecq J: Comparative anticonvulsant activity and neurotoxicity of 4-amino-N-(2,6-dimethylphenyl)-phthalimide and prototype antiepileptic drugs in mice and rats. Epilepsia 1995;36:559-565.
38. Poupaert J, Hamoir G, Barbeaux P, Lambert D, Henichart JP: Anticonvulsant activity of some N-phenylphthalimide derivatives in rats and mice. J Pharm Pharmacol 1995;47:89-91.
39. McQuay H, Carroll D, Jadad AR, Wiffen P, Moore A: Anticonvulsant drugs for the management of pain: a systematic review. Br Med J 1995;311:1047-1052.