γ-aminobutyric acid amides of nortriptyline and fluoxetine display improved pain suppressing activity

Journal of Medicinal Chemistry

Volumn 52, Issue 9, 2009, Pages 3010-3017

  Rephaeli, Ada ^a   Gil Ad, Irit ^a   Aharoni, Ana ^b   Tarasenko, Igor ^a   Tarasenko, Nataly ^a   Geffen, Yona ^c   Halbfinger, Efrat ^c   Nisemblat, Yotam ^c   Weizman, Abraham ^a   Nudelman, Abraham ^b  

^a TEL AVIV UNIVERSITY   (Israel)

^b BAR ILAN UNIVERSITY   (Israel)

^c BioLine Innovations Jerusalem   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

10,11 DIHYDRO 5 (3 METHYLAMINOPROPYLIDENE) 5H DIBENZO[1,4]CYCLOHEPTENE 4 AMINO N BUTANAMIDE; 4 AMINOBUTYRIC ACID DERIVATIVE; FLUOXETINE; GABAPENTIN; N [3 [3 (TRIFLUOROMETHYL)PHENOXY] 3 PHENYLPROPYL] 4 AMINO N ETHYLBUTANAMIDE; NORTRIPTYLINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; CONTROLLED STUDY; CYTOKINE RELEASE; DRUG EFFICACY; DRUG STRUCTURE; EDEMA; HYPERALGESIA; MALE; MOUSE; NONHUMAN; OPEN FIELD TEST; PAIN; RAT;

ANALGESICS; ANIMALS; ANTIDEPRESSIVE AGENTS; ANXIETY; BEHAVIOR, ANIMAL; FLUOXETINE; FORMALDEHYDE; GAMMA-AMINOBUTYRIC ACID; INFLAMMATION; MALE; MICE; NORTRIPTYLINE; PAIN; RATS;

EID: 65649110927     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900143u     Document Type: Article

References (27)

1. Kennedy, J. D. Neuropathic pain: molecular complexity underlies continuing unmet medical need. J. Med. Chem. 2007, 50, 2547-2556. (Pubitemid 46896058)
2. Dworkin, R. H.; O'Connor, A. B.; Backonja, M.; Farrar, J. T.; Finnerup, N. B.; Jensen, T. S.; Kalso, E. A.; Loeser, J. D.; Miaskowski, C.; Nurmikko, T. J.; Portenoy, R. K.; Rice, A. S.; Stacey, B. R.; Treede, R. D.; Turk, D. C.; Wallace, M. S. Pharmacologic management of neuropathic pain: evidence-based recommendations. Pain 2007, 132, 237-251. (Pubitemid 350051570)
3. Gureje, O.; Simon, G. E.; Von Korff, M. A cross-national study of the course of persistent pain in primary care. Pain 2001, 92, 195-200. (Pubitemid 32367950)
4. Sloss, E. M.; Solomon, D. H.; Shekelle, P. G.; Young, R. T.; Saliba, D.; MacLean, C. H.; Rubenstein, L. Z.; Schnelle, J. F.; Kamberg, C. J.; Wenger, N. S. Selecting target conditions for quality of care improvement in vulnerable older adults. J. Am. Geriatr. Soc. 2000, 48, 363-369.
5. Jasmin, L.; Wu, M. V.; Ohara, P. T. GABA puts a stop to pain. Curr. Drug Targets: CNS Neurol. Disord. 2004, 3, 487-505.
6. Chen, H. S.; Lipton, S. A. The chemical biology of clinically tolerated NMDA receptor antagonists. J. Neurochem. 2006, 97, 1611-1626.
7. Zhou, Z.; Zhen, J.; Karpowich, N. K.; Goetz, R. M.; Law, C. J.; Reith, M. E.; Wang, D. N.; Leu, T. Desipramine structure reveals how antidepressants block neurotransmitter reuptake. Science 2007, 317, 1390-1393.
8. Singh, S. K.; Yamashita, A.; Gouaux, E. Antidepressant binding site in a bacterial homologue of neurotransmitter transporters. Nature (London) 2007, 448, 952-956. (Pubitemid 47312772)
9. Max, M. B.; Lynch, S. A.; Muir, J.; Shoaf, S. E.; Smoller, B.; Dubner, R. Effects of desipramine, amitriptyline, and fluoxetine on pain in diabetic neuropathy. N. Engl. J. Med. 1992, 326, 1250-1256.
10. Jann, M. W.; Slade, J. H. Antidepressant agents for the treatment of chronic pain and depression. Pharmacotherapy 2007, 27, 1571-1587. (Pubitemid 350060211)
11. Bryson, H. M.; Wilde, M. I. Amitriptyline. A review of its pharmacological properties and therapeutic use in chronic pain states. Drugs Aging 1996, 8, 459-476. (Pubitemid 26163141)
12. Max, M. B.; Culnane, M.; Schafer, S. C.; Gracely, R. H.; Walther, D. J.; Smoller, B.; Dubner, R. Amitriptyline relieves diabetic neuropathy pain in patients with normal or depressed mood. Neurology 1987, 37, 589-596. (Pubitemid 17057933)
13. McQuay, H. J.; Carroll, D.; Glynn, C. J. Dose-response for analgesic effect of amitriptyline in chronic pain. Anaesthesia 1993, 48, 281-285. (Pubitemid 23135505)
14. McQuay, H. J.; Tramer, M.; Nye, B. A.; Carroll, D.; Wiffen, P. J.; Moore, R. A. A systematic review of antidepressants in neuropathic pain. Pain 1996, 68, 217-227. (Pubitemid 27025878)
15. Leventhal, L.; Smith, V.; Hornby, G.; Andree, T. H.; Brandt, M. R.; Rogers, K. E. Differential and synergistic effects of selective norepinephrine and serotonin reuptake inhibitors in rodent models of pain. J. Pharmacol. Exp. Ther. 2007, 320, 1178-1185.
16. Melzack, R.; Wall, P. D. Pain mechanisms: a new theory. Science 1965, 150, 971-979. (Pubitemid 24154943)
17. Zeilhofer, H. U. Loss of glycinergic and GABAergic inhibition in chronic pain-contributions of inflammation and microglia. Int. Immunopharmacol. 2008, 8, 182-187.
18. Moore, K. A.; Kohno, T.; Karchewski, L. A.; Scholz, J.; Baba, H.; Woolf, C. J. Partial peripheral nerve injury promotes a selective loss of GABAergic inhibition in the superficial dorsal horn of the spinal cord. J. Neurosci. 2002, 22, 6724-6731.
19. Davies Hendrich, J.; Van Minh, A. T.; Wratten, J.; Douglas, L.; Dolphin, A. C. Functional biology of the alpha(2)delta subunits of voltage-gated calcium channels. Trends Pharmacol. Sci. 2007, 28, 220-228.
20. Nudelman, A.; Rephaeli, A.; Gil-Ad, I.; Weizman, A. Conjugates Comprising a GABA-or Glycine Compound, Pharmaceutical Compositions and Combinations Thereof as Well as Their Use in Treating CNS Disorders. PCT/IL2007/000903, 2007.
21. (a) Nudelman, A.; Gil-Ad, I.; Shpaisman, N.; Terasenko, I.; Ron, H.; Stavisky, K.; Geffen, Y.; Weizman, A.; Rephaeli, A. A mutual prodrug ester of GABA and perphenazine exhibits antischizophrenic efficacy with diminished extrapyramidal effects. J. Med. Chem. 2008, 51, 2858-2862.
22. (b) Geffen, Y.; Nudelman, A.; Gil-Ad, I.; Rephaeli, A.; Huang, M.; Savitsky, K.; Klapper, L.; Winkler, I.; Meltzer, H. Y.; Weizman, A. BL-1020: a novel antipsychotic drug with GABAergic activity and low catalepsy, is efficacious in a rat model of schizophrenia. Eur. Neuropsychopharmacol. 2009, 19, 1-13.
23. Le Bars, D.; Gozariu, M.; Cadden, S. W. Animal models of nociception. Pharmacol. Rev. 2001, 53, 597-652. (Pubitemid 33136239)
24. Hunskaar, S.; Hole, S. The formalin test in mice: dissociation between inflammatory and non-inflammatory pain. Pain 1987, 30, 103-114. (Pubitemid 17094194)
25. Prut, L.; Belzung, C. The open field as a paradigm to measure the effect of drugs on anxiety-like behavior. Eur. J. Pharmacol. 2003, 463, 3-33. (Pubitemid 36205070)
26. Rocha, A. C.; Fernandes, E. S.; Quintão, N. L.; Campos, M. M.; Calixto, J. B. Relevance of tumour necrosis factor-alpha for the inflammatory and nociceptive responses evoked by carrageenan in the mouse paw. Br. J. Pharmacol. 2006, 148, 688-695. (Pubitemid 43993059)
27. Ashton, H.; Young, A. H. GABA-ergic drugs: exit stage left, enter stage right. J. Psychopharmacol. 2003, 17, 174-178.