Natural Products and Bioprospecting    2015, Vol. 5 Issue (3) : 111-127     DOI: 10.1007/s13659-015-0060-8
Review |
Sugar Derivatives of Morphine: A New Window for the Development of Potent Anesthetic Drugs
Shyamal K. Jash1, Dilip Gorai2
1. Department of Chemistry, Saldiha College(Affiliated to the University of Burdwan), Saldiha, Bankura 722 173, West Bengal, India;
2. Department of Chemistry, Kulti College(Affiliated to the University of Burdwan), Kulti, Burdwan 713 343, West Bengal, India
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Abstract  This review provides a short account of carbohydrate derivatives of an important natural drug, morphine, along with their comparative efficacies as anesthetic agent. Sugar derivatives are found to have more prospect as anesthetic drug than morphine itself owing to their enhanced bioavailability. Synthetic schemes of these sugar derivatives and information on related patents are also included in this manuscript.
Keywords Morphine      Morphine glycosides      Synthesis      Bioavailability      Anesthetic agents      Related patents     
Issue Date: 11 February 2018
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Shyamal K. Jash,Dilip Gorai. Sugar Derivatives of Morphine: A New Window for the Development of Potent Anesthetic Drugs[J]. Natural Products and Bioprospecting, 2015, 5(3): 111-127.
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http://npb.kib.ac.cn/EN/10.1007/s13659-015-0060-8     OR     http://npb.kib.ac.cn/EN/Y2015/V5/I3/111
1. R.J. Huxtable, S.K. Schwarz, Mol. Interv. 1, 189-191 (2001)
2. G.J. Kilpatrick, T.W. Smith, Med. Res. Rev. 25, 521-544 (2005)
3. J. Rozycka, J. Gadzinowski, D. Vidyasagar, M. Chuchracki, Arch. Perinat. Med. 16, 92-96 (2010)
4. J.M. MacDougall, X.D. Zhang, W.E. Polgar, T.V. Khroyan, L. Toll, J.R. Cashman, J. Med. Chem. 47, 5809-5815 (2004)
5. P. Kovac, K.C. Rice, Heterocycles 41, 697-707 (1995)
6. A.V. Stachulski, F. Scheinmann, J.R. Ferguson, J.L. Law, K.W. Lumbard, P. Hopkins, N. Patel, S. Clarke, A. Gloyne, S.P. Joel, Bioorg. Med. Chem. Lett. 13, 1207-1214 (2003)
7. C. Schotten, Ber. Dtsch. Chem. Ges. 17, 2544-2547 (1884)
8. E. Baumann, Ber. Dtsch. Chem. Ges. 19, 3218-3222 (1886)
9. G. Arsequell, M. Salvatella, G. Valencia, A. Fernandez-Mayoralas, M. Fontanella, C. Venturi, J. Jimenez-Barbero, E. Marron, R.E. Rodriguez, J. Med. Chem. 52, 2656-2666 (2009)
10. L.H. Welsh, J. Org. Chem. 19, 1409-1415 (1954)
11. K. Wilhelm, K. Edward, Ber. Dtsch. Chem. Ges. 34, 957-981 (1901)
12. H. Yoshimura, K. Oguri, H. Tsukamoto, Chem. Pharm. Bull. 16, 2114-2119 (1968)
13. C. Mannich, Annalen 394, 223-228 (1912)
14. P. Casparis, P. Bechert, Pharm. Acta Helv. 22, 97 (1947)
15. F. Scheinmann, K.W. Lumbard, R.T. Brown, S.P. Mayalarp, International Patent, WO 93/3051, 1993
16. L.N. Beigelman, S.N. Mikhailov, Carbohydr. Res. 203, 324-329 (1990)
17. M. Salvatella, G. Arsequell, G. Valencia, R.E. Rodriguez, Bioorg. Med. Chem. Lett. 14, 905-908 (2004)
18. B. Berrang, C.E. Twine, G.L. Hennessee, F.I. Carroll, Synth. Commun. 5, 231-236 (1975)
19. J.M. MacDougall, X.-D. Zhang, W.E. Polgar, T.V. Khroyan, L. Toll, J.R. Cashman, Bioorg. Med. Chem. Lett. 15, 1583-1586 (2005)
20. P.Y. Law, H.H. Loh, Encycl. Life Sci. 1, 39 (2001)
21. G.M. Pacifici, J. Sawe, L. Kager, A. Rane, Eur. J. Clin. Pharmacol. 22, 553-558 (1982)
22. R.T. Penson, S.P. Joel, M. Roberts, A. Gloyne, S. Beckwith, M.L. Slevin, Br. J. Clin. Pharmacol. 53, 347-354 (2002)
23. R.W. Milne, R.L. Nation, A.A. Somogyi, Drug Metab. Rev. 28, 345-472 (1996)
24. S.E. Bartlett, M.T. Smith, Life Sci. 57, 609-615 (1995)
25. R.T. Penson, S.P. Joel, S. Clark, A. Gloyne, M.L. Slevin, J. Pharm. Sci. 90, 1810-1816 (2001)
26. S.J. Peat, M.H. Hanna, M. Woodham, A.A. Knibb, J. Ponte, Pain 45, 101-104 (1991)
27. P.I. Thompson, S.P. Joel, L. John, J.A. Wedzicha, M. Maclean, M.L. Slevin, Br. J. Clin. Pharmacol. 40, 145-152 (1995)
28. S.V. Loser, J. Meyer, S. Freudenthaler, M. Sattler, C. Desel, I. Meineke, U. Gundert-Remy, Naunyn-Schmiedeberg's. Arch. Pharmacol. 354, 192-197 (1996)
29. H.H. Villesen, K. Kristensen, S.H. Hansen, N.-H. Jensen, U. Skram, L.L. Christrup, Eur. J. Clin. Pharmacol. 63, 761-767 (2007)
30. U. Bickel, O.P. Schumacher, Y.S. Kang, K. Voigt, J. Pharmacol. Exp. Ther. 278, 107-113 (1996)
31. D. Wu, Y.S. Kang, U. Bickel, W.M. Pardridge, Drug Metab. Dispos. 25, 768-771 (1997)
32. F. Stain-Texier, G. Boschi, P. Sandouk, J.M. Scherrmann, Br. J. Pharmacol. 128, 917-924 (1999)
33. J. Huwyler, J. Drewe, C. Klusemann, G. Fricker, Br. J. Pharmacol. 118, 1879-1885 (1996)
34. S.P. Letrent, G.M. Pollack, K.R. Brouwer, K.L. Brouwer, Drug Metab. Dispos. 27, 827-834 (1999)
35. R. Xie, M. Hammarlund-Udenaes, A.G. de Boer, E.C. de Lange, Br. J. Pharmacol. 128, 563-568 (1999)
36. P.A. Carrupt, B. Testa, A. Bechalany, N. Tayar, P. Descas, D. Perrissoud, J. Med. Chem. 34, 1272-1275 (1991)
37. P. Gaillard, P.A. Carrupt, B. Testa, Faltou Nome Do Jornal 4, 737 (1994)
38. A. Avdeef, D.A. Barrett, P.N. Shaw, R.D. Knaggs, S.S. Davis, J. Med. Chem. 39, 4377-4381 (1996)
39. CeNeS Pharmaceuticals:News updates September 28, 2006 and October 19, 2006. News release and further information, http://www.cenes.com. Accessed 12 Apr 2015
40. G.E. Mallory, US2062324, 1 Dec 1936
41. C.L. Mehltretter, F.B. Weakley, US2715627, 16 Aug 1955
42. R.R. Tuttle, R. Dixon, M.M. Smulkowski, EP0324212A1, 19 Jul 1989
43. A.A.H. Mertz, WO1993005057A1, 18 Mar 1993
44. R.T. Brown, N.E. Carter, F. Scheinmann, N.J. Turner, WO1995016050A1, 15 Jun 1995
45. G.F. Elkhoury, C. Stein, US5589480, 31 Dec 1996
46. S. Merrill, A.D. Ayer, P. Hwang, A.L. Kuczynski, US5593695, 14 Jan 1997
47. F. Scheinmann, K.W. Lumbard, R.T. Brown, S.P. Mayalarp, N.E. Carter, US5621087, 15 Apr 1997
48. S. Merrill, A.D. Ayer, P. Hwang, A. L. Kuczynski, US5667805, 16 Sept 1997
49. G.F. Elkhoury, US5866143, 2 Feb 1999
50. F. Scheinmann, S. Joel, and A.V. Stachulski, US5977326, 2 Nov 1999
51. F. Scheinmann, K.W. Lumbard, R.T. Brown, S.P. Mayalarp, N.E. Carter, US6046313, 4 Apr 2000
52. J. Ma, R.C. Corcoran, US6054584, 25 Apr 2000
53. P.J. Parsons, R.A. Ewin, US6566510B1, 20 May 2003
54. F. Gao, J. Miotto, EP1412368B1, 28 Apr 2004
55. F. Gao, J. Miotto, US6740641 B2, 25 May 2004
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