Ohmefentanyl and its stereoisomers: Chemistry and pharmacology

Current Medicinal Chemistry

Volumn 4, Issue 4, 1997, Pages 247-270

  Brine, G A ^a   Carroll, F I ^a   Richardson Leibert, T M ^a   Xu, H ^b   Rothman, R B ^b  

^a RTI INTERNATIONAL   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA HYDROXYMEFENTANYL; CARFENTANIL; FENTANYL; FENTANYL DERIVATIVE; MORPHINE; OPIATE; OPIATE RECEPTOR; SUFENTANIL;

ANALGESIC ACTIVITY; ANTINOCICEPTION; BINDING AFFINITY; DRUG ACTIVITY; DRUG RECEPTOR BINDING; MONKEY; MOUSE; NONHUMAN; RABBIT; RAT; REVIEW; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

EID: 0030791387     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (70)

1. Chi, Z.-Q.; Xu, H.; Jin, M.-J.; Zhu, Y.-C.; Ye, S.-Z.; Zou, D.-H. In Retrosp. Prospect Protein Res.; Li, Z.-P.; Lu, Z.-X.; Zhang, Y.-S., Eds.; World Science: Singapore, 1991, p 131.
2. Casy, A. F.; Parfitt, R.T. In Opioid Analgesics. Chemistry and Receptors; Plenum Press: New York, New York, 1986, Chapter 8, p 287.
3. Bagley, J.R.; Kudzma, L.V.; Lalinda, N.L.; Colapret, J.A.; Huang, B.-S.; Lin, B.-S.; Jerussi, T.P.; Benvenga, M.J.; Doorley, B.M.; Ossipov, M.H.; Spaulding, T.C.; Spencer, H.K.; Rudo, F.G.; Wynn, R.L. Med. Res. Reviews, 1991, 11, 403.
4. Van Bever, W.F.M.; Niemegeers, C.J.E.; Janssen, P.A.J. J. Med. Chem., 1974, 17, 1047.
5. Van Bever, W.F.M.; Niemegeers, C.J.E.; Schellekens, K.H.L.; Janssen, P.A.J. Arzneim.-Forsch., 1976, 26, 1548.
6. Jin, W.-Q.; Xu, H.; Zhu, Y.-C.; Fang, S.-N.; Xia, X.-L.; Huang, Z.-M.; Ge, B.-L.; Chi, Z.-Q. Sci. Sinica (Engl. Ed.), 1981, 24, 710.
7. Zhu, Y.-C.; Fang, S.-N.; Ge, N.-L.; Li, Q.-Z.; Dai, Q.-Y.; Huang, Z.-M.; Wu, R.-Q.; Zhang, H.-P. Acta Pharmaceut. Sin., 1981, 16, 97.
8. Zhu, Y.-C.; Wu, R.-Q.; Chou, D.-P.; Huang, Z.-M. Acta Pharmaceut. Sci., 1983, 18, 900.
9. Carabateas, P.M.; Grumbach, L. J. Med. Pharm. Chem., 1962, 5, 913.
10. Fifer, E.K.; Davis, W.M.; Borne, R.F. Eur. J. Med. Chem. - Chim. Ther., 1984, 19, 519.
11. Huang, Z.-M.; Zhou, J.; Chen, X.-J.; Zheng, W.-J.; Zhang, H.-P.; Chi, Z.-Q.; Li, Z.-G.; Chen, W.-L. Acta Pharmacol. Sin., 1984, 5, 153.
12. Xu, H.; Chen, J.; Chi, Z.-Q. Sci. Sinica (Series B), 1985, 28, 504.
13. Xu, H.; Yao, Y.-H.; Zhu, Y.-C.; Chen, J.; Chi, Z.-Q. Acta Pharmacol. Sin., 1987, 8, 289.
14. Xu, H.; Kim, C.-H.; Zhu, Y.-C.; Weber, R.J.; Jacobson, A.E.; Rice, K.C.; Rothman, R.B. Neuropharmacol., 1991, 30, 455.
15. Jin, W.-Q.; Chen, X.-J.; Chi, Z.-Q. Sci. Sinica (Series B), 1987, 30, 176.
16. Baum, R.M. Chem. Eng. News, 1985, 63, 7.
17. Van Daele, P.G.H.; De Bruyn, M.F.L; Boey, J.M.; Sanozuk, S.; Agten, J.T.M.; Janssen, P.A.J. Arzneim.-Forsch., 1976, 26, 1521.
18. Aceto, M.D.; Bowman, E.R.; Harris, L.S.; May, E.L. In Problems of Drug Dependence, 1988. Proceedings of the 50th Annual Scientic Meeting. The Committee on Problems of Drug Dependence, Inc.; Harris, L.S., Ed., 1988, NIDA Research Monograph 90, p 468.
19. Woods, J.H.; Medzihradsky, F.; Smith, C.B.; Winger, G.D.; France, C.P. In Problems of Drug Dependence, 1988. Proceedings of the 50th Annual Scientific Meeting. The Committee on Problems of Drug Dependence, Inc.; Harris, L.S., Ed., 1988, NIDA Research Monograph 90, p 421.
20. Rothman, R.B.; Xu, H.; Seggel, M.; Jacobson, A.E.; Rice, K.C.; Brine, G.A.; Carroll, F.I. Life Sci., 1991, 48, PL111.
21. Posner, G.H.; Rogers, D.Z. J. Am. Chem. Soc., 1977, 99, 8214.
22. Brine, G.A.; Sawyer, D.K.; Huang, P.-T.; Stark, P.A.; Gaetano, K.D.; Carroll, F.I. J. Heterocyclic Chem., 1992, 29, 1773.
23. Zhou, D.-H.; Ni, C.-H.; Wu, Y.-Z.; Li, Z.-Y.; Liu, J.-Z.; Tang, G.-Z.; Zhao, X.-L. Acta Pharmacol. Sin., 1982, 17.
24. Wang, H.; Pelaprat, D.; Roques, B.P.; Vanhove, A.; Chi, Z.-Q.; Rostene, W. Eur. J. Pharmacol., 1991, 193, 341.
25. Goldstein, A.; Naidu, A. Mol. Pharmacol., 1989, 36, 265.
26. Wang, H.; Sarrieau, A.; Pelaprat, D.; Roques, B.P.; Vanhove, A.; Kopp, N.; Chi, Z.-Q.; Rostene, W. Synapse, 1991, 8, 177.
27. Masuo, Y.; Wang, H.; Pelaprat, D.; Chi, Z.-Q.; Rostene, W. Chem. Pharm. Bull., 1992, 40, 2520.
28. Zhu, Y.C.; Prenant, C.; Crouzel, C.; Comar, D.; Chi, Z.-Q. J. Labelled Compd. Radiopharm., 1992, 31, 853.
29. Chen, C.; Li, L. Int. J. Quantum Chem., 1983, 23, 1597.
30. Zhu, Y.-C.; Wu, J.; Xu, X. Acta Pnarmaceut. Sci., 1985, 20, 267.
31. Wen, S.; Yang, Y.; Shao, H.-Z.; Yang, Z.; Liu, L.; Chen, J. Zhongguo Yoake Daxue Xuebao. 1992, 23, 196.
32. Aceto, M.D.; Bowman, E.R.; Harris, L.S.; May, E.L, In Problems of Drug Dependence, 1992. Proceedings of the 54th Annual Scientific Meeting. The College on Problems of Drug Dependence, Inc.; Harris, L.S., Ed., 1993, NIDA Research Monograph 132, p 459.
33. Aceto, M.D.; Bowman, E.R.; Harris, L.S.; May, E.L. In Problems of Drug Dependence, 1993. Proceedings of the 55th Annual Scientific Meeting. The College on Problems of Drug Dependence, Inc.; Harris, U.S., Ed., 1994, NIDA Research Monograph 140, p 103.
34. Aceto, M.D.; Bowman, E.R.; Harris, L.S.; May, E.L. In Problems of Drug Dependence, 1994. Proceedings of the 56th Annual Scientific Meeting. The College on Problems of Drug Dependence, Inc.; Harris, L.S., Ed., 1995, NIDA Research Monograph 152, p 162.
35. Brine, G.A.; Stark, P.A.; Carroll, F.I.; Xu, H.; Lewis, B.; Rothman, R.B. Med. Chem. Res., 1992, 2, 41.
36. Weng, J.-H.; Xu, X.-R.; Zhu, Y.-C.; Zhou, J.; Xu, H.; Chi, Z.-Q. Acta Pharmaceut. Sin., 1990, 25, 178.
37. Woods, J.H.; Medzihradsky, F.; Smith, C.B.; France, C.P.; Winger, G.D. In Problems of Drug Dependence, 1994. Proceedings of the 56th Annual Scientific Meeting. The College on Problems of Drug Dependence, Inc.; Harris, L.S., Ed., 1995, NIDA Research Monograph 152, p 117.
38. Woods, J.H.; France, C.P.; Medzihradsky, F.; Smith, C.B.; Winger, G.D. In Problems of Drug Dependence, 1993. Proceedings of the 55th Annual Scientific Meeting. The College on Problems of Drug Dependence, Inc.; Harris, L.S., Ed., 1994, NIDA Research Monograph 140, p 196.
39. Cotton, R.; Giles, M.G.; Miller, L.; Shaw, J.S.; Timms, D. Eur. J. Pharmacol., 1984, 97, 331.
40. Woods, J.H.; France, C.P.; Medzihradsky, F.; Smith, C.B.; Winger, G.D. In Problems of Drug Dependence, 1992. Proceedings of the 54th Annual Scientific Meeting. The College on Problems of Drug Dependence, Inc.; Harris, L.S., Ed., 1993, NIDA Research Monograph 132, p 517.
41. France, C.P.; Gerak, L.R.; Flynn, D.; Winger, G.D.; Medzihradsky, F.; Bagley, J.R.; Brockunier, L.L.; Woods, J.H. J. Pharmacol. Exp. Ther., 1995, 274, 17.
42. Bagley, J.R.; Wynn, R.L.; Rudo, F.G.; Doorley, B.M.; Spencer, H.K.; Spaulding, T. J. Med. Chem., 1989, 32, 663.
43. Wang, Z.-X.; Zhu, Y.-C.; Chen, X.-J.; Ji, R.-Y. Chin. Sci. Bull., 1994, 39, 2004.
44. Chi, Z.-Q.; Wang, Z.-X.; Zhu, Y.-C.; Jin, W.-Q. Regul. Pept., 1994, 54, 59.
45. Wang, Z.-X.; Zhu, Y.-C.; Jin, W.-Q.; Chen, X.-J.; Chen, J.; Ji, R.-Y.; Chi, Z.-Q. J. Med. Chem, 1995, 38, 3652.
46. Burke, T.R., Jr.; Jacobson, A.E.; Rice, K.C.; Silverton, J.V.; Simonds, W.F.; Streaty, R.A.; Klee, W.A. J. Med. Chem., 1986, 29, 1087.
47. Kim, C.-H.; Rothman, R.B.; Jacobson, A.E.; Mattson, M.V.; Bykov, V.; Streaty, R.A.; Klee, W.A.; George, C.; Long, J.B.; Rice, K.C. J. Med. Chem., 1989, 32, 1392.
48. Brine, G.A.; Stark, P.A.; Liu, Y.; Carroll, F.I.; Singh, P.; Xu, H.; Rothman, R.B. J. Med. Chem., 1995, 38, 1547.
49. Gao, J.-H.; Wang, Z.-X.; Song, G.-Q.; Zhu, Y.-C.; Ji, R.-Y. Acta Chim. Sin., 1995, 53, 900.
50. Wang, Z.-X.; Zhu, Y.-C.; Jiang, N.; Ji, R.-Y. Acta Pharmacol. Sin., 1995, 30, 500.
51. Jin, W.-Q.; Wang, Z.-X.; Chen, J.; Chen, X.-J.; Chi, Z.-Q. Acta Pharmacol. Sin., 1996, 17, 421.
52. Brine, G.A.; Stark, P.A.; Carroll, F.I.; Xu, H.; Rothman, R.B. Med. Chem. Res., 1992, 2, 34.
53. Xu, H.; Lu, Y.-L.; Partilla, J.S.; Brine, G.A.; Carroll, F.I.; Rice, K.C.; Lai, J.; Porreca, F.; Rothman, R.B. Analgesia, 1997, in press
54. Ni, Q.; Xu, H.; Partilla, J.S.; Stark, P.A.; Carroll, F.I.; Brine, G.A.; Rothman, R.B. Synapse, 1993, 15, 296.
55. Traynor, J.R.; Nahorski, S.R. Mol. Pharmacol., 1995, 47, 848.
56. Sim, L.J.; Selley, D.E.; Childers, S.R. Proc. Natl. Acad. Sci. USA, 1995, 92, 7242.
57. Emmerson, P.J.; Clark, M.J.; Mansour, A.; Akil, H.; Woods, J.H.; Medzihradsky, F. J. Pharmacol. Exp. Ther., 1996, 278, 1121.
58. Lu, Y.-F.; Xu, H.; Liu-Chen, L.-Y.; Chen, C.; Partilla, J.S.; Brine, G.A.; Carroll, F.I.; Rice, K.C.; Lai, J.; Porreca, F.; Sadee, W.; Rothman, R.B. Synapse, 1997, in press.
59. Lu, Y.-F.; Xu, H.; Partilla, J.S.; Brine, G.A.; Carroll, F.I.; Rice, K.C.; Sadee, W.; Rothman, R.B. Analgesia, 1996, 2, 291.
60. Rice, K.C.; Jacobson, A.E.; Burke, T.R., Jr.; Bajwa, B.S.; Streaty, R.A.; Klee, W.A. Science, 1983, 220, 314.
61. Wang, Z.X.; Zhu, Y.C.; Ji, R.Y. Chin. Chem. Lett., 1995, 6, 759.
62. Tollenaere, J.P.; Moereels, H.; Van Loon, M. In Progress in Drug Research; Jucker, E., Ed.; Birkhauser Verlag: Basel, 1986; Vol. 30, p91.
63. Martin, J.; Andrews, P. J. Comput-Aided Mol. Design, 1987, 1, 53.
64. Froimowitz, M. In Problems of Drug Dependence, 1989. Proceedings of the 51st Annual Scientific Meeting. The Committee on Problems of Drug Dependence, Inc.; Harris, L.S., Ed., 1989, NIDA Research Monograph 95, p 302.
65. Li, Y.-L.; Lian, H.; Hu, J.; Chen, C.-Y.; Chen, J.-H.; Xu, X.; Guan, Y.; Luo, Y.; Tang, Y.-Q. Acta Physico-Chimica Sin., 1989, 5, 681.
66. Cometta-Monni, C.; Loew, G.H. J. Comput.-Aided Mol. Design, 1991, 5, 335.
67. Cometta-Morini, C.; Maguire, P.A.; Loew, G.H. Mol. Pharmacol., 1992, 41, 185.
68. Brandt, W.; Barth, A.; Holtje, H.-D. Drug Des. Discovery, 1993, 10, 257.
69. Dosen-Micovic, L.J.; Ivanovic, M.; Roglic, G.; Micovic, V. J. Serb. Chem. Soc., 1996, 61, 1075.
70. Nie, Z.-Z; Zhang, K.-G.; Wang, C.-Q. Acta Pharmacol. Sin., 1989, 10, 201.