The development of ultrashort acting neuromuscular relaxant tropane derivatives

Journal of Critical Care

Volumn 24, Issue 1, 2009, Pages 58-65

  Gyermek, Laszlo ^a   Lee, Chingmuh ^a  

^a HARBOR UCLA MEDICAL CENTER   (United States)

Author keywords

Molecular design; Neuromuscular relaxants; Rapid onset of action; Short duration of action; Structure Activity relationships

Indexed keywords

AMINOSTEROID DERIVATIVE; DF 596; G 1 64; GRANATANOLINIUM; MIVACURIUM; MUSCLE RELAXANT AGENT; N,N' ATROPINIUM; ROCURONIUM; SUXAMETHONIUM; TAAC 3; TETRAHYDROISOQUINOLINE DERIVATIVE; TROPINE; UNCLASSIFIED DRUG;

DRUG MECHANISM; DRUG STRUCTURE; REVIEW; STRUCTURE ACTIVITY RELATION;

ANESTHESIA RECOVERY PERIOD; ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; BINDING SITES; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; DRUG INTERACTIONS; FORECASTING; HUMANS; METABOLIC CLEARANCE RATE; NEUROMUSCULAR BLOCKADE; NEUROMUSCULAR NONDEPOLARIZING AGENTS; PATIENT SELECTION; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS; TISSUE DISTRIBUTION; TROPANES;

EID: 61449170920     PISSN: 08839441     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jcrc.2008.08.005     Document Type: Review

References (44)

1. Bovet-Nitti F. Les curares a brève durée d' action. In: Bovet D., Bovet-Nitti F., and Marini-Bettolo G. (Eds). Curare and curare like agents (1959), Elsevier Publ, Amsterdam 234-243
2. Savarese J., and Kitz R.J. The quest for a short acting nondepolarizing neuromuscular blocking agent. Acta Anaesthesiol Scand Suppl 53 (1973) 48-58
3. Bovet D. Synthetic inhibitors of neuromuscular transmission, chemical structures and structure-activity relationships. Internat Encycl Pharmacol Chapter II, Sect 14 Vol. I (1972), Pergamon Press, Oxford 243-294
4. Stenlake J.B., Urwin J., and Waigh D. Biodegradable neuromuscular blocking agents. I.Quaternary esters. Eur J Med Chem 14 (1979) 77-84
5. Stenlake J.B., Waigh R.D., Dewar G.H., et al. Biodegradable neuromuscular blocking agents. Part 4. Atracurium besylate and related polyalkylene di-esters. Eur J Med Chem 16 (1981) 515-524
6. Savarese J.J., Belmont M.R., Cohn D.L., et al. Some SAR among isoquinolinium fumarate diesters leading to the identification of AV 002. Annual Meeting A.S.A. San Francisco A386 (2007)
7. Bowman W.C., Rodger I.W., Houston J., et al. Structure: action relationships among some desacetoxy analogues of pancuronium and vecuronium in the anesthetized cat. Anesthesiology 69 (1988) 57-62
8. Lee C. Structure, conformation and action of neuromuscular blocking drugs. Br J Anaesth 87 (2001) 755-769
9. Gyermek L. Development of ultrashort-acting muscle relaxant agents: history, research strategies and challenges. Med Res Rev 25 (2005) 610-654
10. Wonnacott S., and Barik J. Nicotinic ACh receptors. Tocris reviews series, No 28 (2007), Tocris Cookson Publ, Bristol, UK 1-20
11. Corringer P.J., Bertrand S., Galzi, et al. Molecular basis of the charge selectivity of nicotinic acetylcholine receptor and related ligand-gated ion channels. Novartis Found Symp 225 (1999) 215-224
12. Gyermek L., and 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 3 (1952) 283-293
13. Bowman W.C. Non-relaxant effects of neuromuscular blocking drugs. Br J Anaesth 54 (1982) 147-160
14. Donati F. Effect of dose and potency on onset. Anaesth Pharmacol Rev 1 (1993) 34-43
15. Hansch C., and Leo A. Calculations of octanol-water partition coefficients by fragments. Chapter 5. Exploring QSAR. Fundamentals and applications in chemistry and biology. (1995), Am Chem Society Publ, Washington, D.C. 125-168
16. Roy J.J., and Varin F. Physicochemical properties of neuromuscular blocking agents and their impact on the pharmacokinetic-pharmacodynamic relationship. Br J Anaesth 93 (2004) 241-248
17. Beaufort T.M., Nigrovich V., Proost J.H., et al. Inhibition of the enzyme degradation of suxamethonium and mivacurium increases the onset time of submaximal neuromuscular block. Anesthesiology 89 (1998) 707-714
18. Lainweber F.J. Possible physiological roles of carboxylic ester hydrolases. Drug Metab Rev 18 (1987) 379-439
19. Maclagan J. Competitive neuromuscular blocking agents. In: Zaimis E. (Ed). Handb Exp. Pharmacol Vol. 42, Neuromuscular junction (1976), Springer, Berlin 421-486
20. Proost J.H., Roggweld J., Wierda J.M.K.H., 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 282 (1997) 715-726
21. Ducharme J., and Donati F. Pharmacokinetics and pharmacodynamics of steroidal muscle relaxants. In: Partridge B.L. (Ed). Advances in the use of muscle relaxants (1993), W B Saunders Co, Philadelphia 283-307
22. Glavinovich M.I., Law Min J.C., Kapural L., et al. Speed of action of various muscle relaxants at the neuromuscular junction binding vs. buffering hypothesis. J Pharmacol Exp Ther 265 (1993) 1181-1186
23. Wierda J.M.K.H., Proost J.H., Muir A.W., et al. Design of drugs for rapid onset. Anaesth Pharmacol Rev 1 (1993) 57-89
24. Proost J.H., Wierda J.M., Hoowertjes, et al. Structure-Pharmacokinetics relationship of series of aminosteroidal neuromuscular blocking agents in the cat. J Pharmacol Exp Ther 292 (2000) 861-869
25. Gyermek L., and Nador K. Pharmacology of tropane compounds in relation to their steric structure. J Pharm Pharmacol 9 (1957) 209-229
26. Kimura K.K., and Unna K.R. Curare like action of decamethylene bis-(atropinium) iodide. J Pharmacol Exp Ther 98 (1950) 286-292
27. Kimura K.K., Unna K.R., and Pfeiffer C.C. Diatropine derivatives as proof that d-tubocuraraine is blocking moiety containing twin atropine-acetylcholine prosthetic groups. J Pharmacol Exp Ther 95 (1949) 149-154
28. Gyermek L., and Sztanyik L. The ganglionic blocking activity of tropeines. Acta Physiol Acad Sci Hung 2 (1951) 41-47
29. Gyermek L. The ganglion blocking action of the tropine and tropinium. Acta Physiol Acad Sci Hung 2 (1951) 175-177
30. Nador K., and Gyermek L. Attempts to find new compounds with curare like effects. III. Quaternary derivatives of dicarboxylic acid tropine esters. Acta Chim Hung 2 (1952) 369-374
31. Gyermek L., and Nador K. Studies on cholinergic blocking substances III. Neuromuscular blocking tropeines. Acta Physiol Acad Sci Hung 4 (1953) 159-174
32. Gyermek L. Structure-Action relationships among derivatives of dicarboxylic acid tropine esters. Pharmacol Ther 96 (2002) 1-21
33. Gyermek L, Lee C, Cho YM: Neuromuscular relaxants. US Patent # 5,990.124, 1999.
34. Gyermek L., Lee C., Cho Y.M., et al. Ultrashort acting neuromuscular blocking agents, 1. Di- and trisubstituted benzyl bisquaternary ammonium tropane-3α-ol diesters. Med Chem Res 11 (2002) 316-336
35. Gyermek L., Lee C., and Nguyen N. Pharmacology of G-1-64, a new nondepolarizing neuromuscular blocking agent with rapid onset and short duration of action. Acta Anaesthesiol Scand 43 (1999) 651-657
36. Gyermek L., Lee C., Cho Y.M., et al. Neuromuscular pharmacology of TAAC3, a new nondepolarizing muscle relaxant with rapid onset and ultrashort duration of action. Anesth Analg 94 (2002) 879-985
37. Gyermek L., Lee C., Cho Y.M., et al. Quaternary derivatives of granatanol diesters: potent, ultrashort acting non-depolarizing neuromuscular relaxants. Life Sci 79 (2006) 559-569
38. Haining C.G., Johnston R.G., and Smith J.M. The neuromuscular blocking properties of a series of bis-quaternary tropeines. Br J Pharmacol 15 (1960) 71-78
39. Kharkevich D.A. Chemical structures of neuromuscular blocking agents. In: Agoston Bowman A., and Bowman W.C. (Eds). Muscle Relaxants, Chapter 3 (1990), Elsevier Science Publ, Amsterdam 59-86
40. Gyermek L., Cho Y.M., Nguyen N., et al. Neuromuscular blocking N,N'α-hydroxytropanium and bis-3-oxotropanium compounds. Life Sci 63 (1998) 303-309
41. Interim report, Organon Laboratories.
42. Lee C. Conformation, action and mechanism of action of neuromuscular blocking muscle relaxants. Pharmacol Ther 98 (2003) 143-169
43. Stenlake J.B. Biodegradation and elimination of neuromuscular blocking agent. In: Kharkevich D.A. (Ed). New neuromuscular blocking agents, Chapter 10. Handb Exp Pharmacol Vol. 79 (1986), Springer Publ, Berlin 264-276
44. Khromov-Borisov N.V., Gmiro V.E., and Magazanik L.S. Removal of curare-like effect by direct inactivation of the myorelaxant molecule by rupturing the disulfide bond. Dokl Akad Nauk USSR 186 (1969) 236-239