Journal of Critical Care
Volume 24, Issue 1 , Pages 58-65 , March 2009

The development of ultrashort acting neuromuscular relaxant tropane derivatives

References 

  1. Bovet-Nitti F. Les curares a brève durée d' action.. In:  Bovet D,  Bovet-Nitti F,  Marini-Bettolo G editor. Curare and curare like agents. Amsterdam: Elsevier Publ; 1959;p. 234–243
  2. Savarese J, Kitz RJ. The quest for a short acting nondepolarizing neuromuscular blocking agent. Acta Anaesthesiol Scand Suppl. 1973;53:48–58
  3. Bovet D. Synthetic inhibitors of neuromuscular transmission, chemical structures and structure-activity relationships. In: Internat Encycl Pharmacol Chapter II, Sect 14. Vol. I:Oxford: Pergamon Press; 1972;p. 243–294
  4. Stenlake JB, Urwin J, Waigh D. Biodegradable neuromuscular blocking agents. I.Quaternary esters. Eur J Med Chem. 1979;14:77–84
  5. Stenlake JB, Waigh RD, Dewar GH, et al. Biodegradable neuromuscular blocking agents. Part 4. Atracurium besylate and related polyalkylene di-esters. Eur J Med Chem. 1981;16:515–524
  6. Savarese JJ, Belmont MR, Cohn DL, et al. Some SAR among isoquinolinium fumarate diesters leading to the identification of AV 002. In: Annual Meeting A.S.A. San Francisco A386. 2007;
  7. Bowman WC, Rodger IW, Houston J, et al. Structure: action relationships among some desacetoxy analogues of pancuronium and vecuronium in the anesthetized cat. Anesthesiology. 1988;69:57–62
  8. Lee C. Structure, conformation and action of neuromuscular blocking drugs. Br J Anaesth. 2001;87:755–769
  9. Gyermek L. Development of ultrashort-acting muscle relaxant agents: history, research strategies and challenges. Med Res Rev. 2005;25:610–654
  10. Wonnacott S, Barik J. Nicotinic ACh receptors. In: Tocris reviews series, No 28. Bristol, UK: Tocris Cookson Publ; 2007;p. 1–20
  11. Corringer PJ, Bertrand S, Galzi , et al. Molecular basis of the charge selectivity of nicotinic acetylcholine receptor and related ligand-gated ion channels. Novartis Found Symp. 1999;225:215–224
  12. Gyermek L, Nador K. Studies on cholinergic blocking substances II. Correlations of the antimuscarine, antinicotine and curare-like effects of mono and bisquaternary tropeines. Acta Physiol Acad Sci Hung. 1952;3:283–293
  13. Bowman WC. Non-relaxant effects of neuromuscular blocking drugs. Br J Anaesth. 1982;54:147–160
  14. Donati F. Effect of dose and potency on onset. Anaesth Pharmacol Rev. 1993;1:34–43
  15. Hansch C, Leo A. Calculations of octanol-water partition coefficients by fragments. Chapter 5. In: Exploring QSAR. Fundamentals and applications in chemistry and biology.. Washington, D.C.: Am Chem Society Publ; 1995;p. 125–168
  16. Roy JJ, Varin F. Physicochemical properties of neuromuscular blocking agents and their impact on the pharmacokinetic-pharmacodynamic relationship. Br J Anaesth. 2004;93:241–248
  17. Beaufort TM, Nigrovich V, Proost JH, et al. Inhibition of the enzyme degradation of suxamethonium and mivacurium increases the onset time of submaximal neuromuscular block. Anesthesiology. 1998;89:707–714
  18. Lainweber FJ. Possible physiological roles of carboxylic ester hydrolases. Drug Metab Rev. 1987;18:379–439
  19. Maclagan J. Competitive neuromuscular blocking agents. In:  Zaimis E editors. Handb Exp. Pharmacol Vol. 42, Neuromuscular junction. Berlin: Springer; 1976;p. 421–486
  20. Proost JH, Roggweld J, Wierda JMKH, et al. Relationship between chemical structure and physicochemical properties of series of bulky organic cations and their hepatic uptake and biliary excretion rates. J Pharmacol Exp Ther. 1997;282:715–726
  21. Ducharme J, Donati F. Pharmacokinetics and pharmacodynamics of steroidal muscle relaxants. In:  Partridge BL editors. Advances in the use of muscle relaxants. Philadelphia: W B Saunders Co; 1993;p. 283–307
  22. Glavinovich MI, Law Min JC, Kapural L, et al. Speed of action of various muscle relaxants at the neuromuscular junction binding vs. buffering hypothesis. J Pharmacol Exp Ther. 1993;265:1181–1186
  23. Wierda JMKH, Proost JH, Muir AW, et al. Design of drugs for rapid onset. Anaesth Pharmacol Rev. 1993;1:57–89
  24. Proost JH, Wierda JM, Hoowertjes , et al. Structure-Pharmacokinetics relationship of series of aminosteroidal neuromuscular blocking agents in the cat. J Pharmacol Exp Ther. 2000;292:861–869
  25. Gyermek L, Nador K. Pharmacology of tropane compounds in relation to their steric structure. J Pharm Pharmacol. 1957;9:209–229
  26. Kimura KK, Unna KR. Curare like action of decamethylene bis-(atropinium) iodide. J Pharmacol Exp Ther. 1950;98:286–292
  27. Kimura KK, Unna KR, Pfeiffer CC. Diatropine derivatives as proof that d-tubocuraraine is blocking moiety containing twin atropine-acetylcholine prosthetic groups. J Pharmacol Exp Ther. 1949;95:149–154
  28. Gyermek L, Sztanyik L. The ganglionic blocking activity of tropeines. Acta Physiol Acad Sci Hung. 1951;2:41–47
  29. Gyermek L. The ganglion blocking action of the tropine and tropinium. Acta Physiol Acad Sci Hung. 1951;2:175–177
  30. Nador K, Gyermek L. Attempts to find new compounds with curare like effects. III. Quaternary derivatives of dicarboxylic acid tropine esters. Acta Chim Hung. 1952;2:369–374
  31. Gyermek L, Nador K. Studies on cholinergic blocking substances III. Neuromuscular blocking tropeines. Acta Physiol Acad Sci Hung. 1953;4:159–174
  32. Gyermek L. Structure-Action relationships among derivatives of dicarboxylic acid tropine esters. Pharmacol Ther. 2002;96:1–21
  33. Gyermek L, Lee C, Cho YM: Neuromuscular relaxants. US Patent # 5,990.124, 1999.
  34. Gyermek L, Lee C, Cho YM, et al. Ultrashort acting neuromuscular blocking agents, 1. Di- and trisubstituted benzyl bisquaternary ammonium tropane-3α-ol diesters. Med Chem Res. 2002;11:316–336
  35. Gyermek L, Lee C, Nguyen N. Pharmacology of G-1-64, a new nondepolarizing neuromuscular blocking agent with rapid onset and short duration of action. Acta Anaesthesiol Scand. 1999;43:651–657
  36. Gyermek L, Lee C, Cho YM, et al. Neuromuscular pharmacology of TAAC3, a new nondepolarizing muscle relaxant with rapid onset and ultrashort duration of action. Anesth Analg. 2002;94:879–985
  37. Gyermek L, Lee C, Cho YM, et al. Quaternary derivatives of granatanol diesters: potent, ultrashort acting non-depolarizing neuromuscular relaxants. Life Sci. 2006;79:559–569
  38. Haining CG, Johnston RG, Smith JM. The neuromuscular blocking properties of a series of bis-quaternary tropeines. Br J Pharmacol. 1960;15:71–78
  39. Kharkevich DA. Chemical structures of neuromuscular blocking agents. In:  Agoston Bowman A,  Bowman WC editor. Muscle Relaxants, Chapter 3. Amsterdam: Elsevier Science Publ; 1990;p. 59–86
  40. Gyermek L, Cho YM, Nguyen N, et al. Neuromuscular blocking N,N'α-hydroxytropanium and bis-3-oxotropanium compounds. Life Sci. 1998;63:303–309
  41. Interim report, Organon Laboratories.
  42. Lee C. Conformation, action and mechanism of action of neuromuscular blocking muscle relaxants. Pharmacol Ther. 2003;98:143–169
  43. Stenlake JB. Biodegradation and elimination of neuromuscular blocking agent. In:  Kharkevich DA editors. New neuromuscular blocking agents, Chapter 10. Handb Exp Pharmacol. Vol. 79:Berlin: Springer Publ; 1986;p. 264–276
  44. Khromov-Borisov NV, Gmiro VE, Magazanik LS. Removal of curare-like effect by direct inactivation of the myorelaxant molecule by rupturing the disulfide bond. Dokl Akad Nauk USSR. 1969;186:236–239

PII: S0883-9441(08)00181-0

doi: 10.1016/j.jcrc.2008.08.005

Journal of Critical Care
Volume 24, Issue 1 , Pages 58-65 , March 2009