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Volumn 16, Issue 19, 2009, Pages 2468-2474

Fentanyl analogs: Structure-activity-relationship study

Author keywords

Analgesic activity; Analogs; Fentanyl; Neurotoxicity; Structure activity relationship (SAR)

Indexed keywords

3 ALLYLFENTANYL; 3 BENZYLFENTANYL; 3 BUTYL FENTANYL; 3 CARBOMETHOXYFENTANYL; 3 ETHYLFENTANYL; 3 ISOPROPYLFENTANYL; 3 PHENETHYLFENTANYL; 3 PROPYLFENTANYL; 4 METHYLFENTANYL; CARFENTANIL; FENTANYL; FENTANYL DERIVATIVE; MEFENTANYL; MORPHINE; UNCLASSIFIED DRUG;

EID: 70349386048     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986709788682074     Document Type: Review
Times cited : (66)

References (70)
  • 1
    • 33646437796 scopus 로고    scopus 로고
    • Brunton, L.L, Lazo, J.S, Parker, K.L, Eds, 11th Ed; McGraw-Hill Medical Publishing Division: New York, Chapter 21
    • Gutstein, H.B.; Akil, H. In Goodman & Gilman's The Pharmacological Basis of Therapeutics; Brunton, L.L.; Lazo, J.S.; Parker, K.L., Eds.; 11th Ed; McGraw-Hill Medical Publishing Division: New York, Chapter 21, 2006; pp. 547-90.
    • (2006) Goodman & Gilman's The Pharmacological Basis of Therapeutics , pp. 547-590
    • Gutstein, H.B.1    Akil, H.2
  • 2
    • 70349396021 scopus 로고    scopus 로고
    • Casy, A.F.; R. Parfitt, T.; Opioid Analgesics, Plenum Press: N. Y., USA, 1986; pp. 287-301.
    • Casy, A.F.; R. Parfitt, T.; Opioid Analgesics, Plenum Press: N. Y., USA, 1986; pp. 287-301.
  • 3
    • 84873788346 scopus 로고
    • The inhibitory effect of fentanyl and other morphine-like analgesics on the warm water induced tail withdrawal reflex in rats
    • Janssen, P.A.J.; Niemegeers, C.J.E.; Dony, J.G.H. The inhibitory effect of fentanyl and other morphine-like analgesics on the warm water induced tail withdrawal reflex in rats. Arzneimittel-Forsch. (Drug Res.), 1963, 13, 502-7.
    • (1963) Arzneimittel-Forsch. (Drug Res.) , vol.13 , pp. 502-507
    • Janssen, P.A.J.1    Niemegeers, C.J.E.2    Dony, J.G.H.3
  • 4
    • 0017115101 scopus 로고
    • Sufentanil, a very potent and extremely safe intravenous morphine-like compound in mice, rats and dogs
    • Niemegeers, C.J.; Schellekens, K.H.; Van Bever, W.F.; Janssen, P.A. Sufentanil, a very potent and extremely safe intravenous morphine-like compound in mice, rats and dogs. Arzneimittelforschung. 1976, 26, 1551-6.
    • (1976) Arzneimittelforschung , vol.26 , pp. 1551-1556
    • Niemegeers, C.J.1    Schellekens, K.H.2    Van Bever, W.F.3    Janssen, P.A.4
  • 5
    • 70349385043 scopus 로고    scopus 로고
    • The Merck Index, 13th Ed., Merck & Co., Inc., New York, 2002.
    • The Merck Index, 13th Ed., Merck & Co., Inc., New York, 2002.
  • 6
    • 0018199605 scopus 로고
    • Immobilisation of free-ranging wild animals using a new drug
    • De Vos, V. Immobilisation of free-ranging wild animals using a new drug. Vet Rec., 1978, 103, 64-8.
    • (1978) Vet Rec , vol.103 , pp. 64-68
    • De Vos, V.1
  • 7
    • 0020332541 scopus 로고
    • Binding properties of 3H-lofentanil at the opiate receptor
    • Gommeren, W.; Leysen, J.E. Binding properties of 3H-lofentanil at the opiate receptor. Arch. Int. Pharmacodyn. Ther., 1982, 258, 171-3.
    • (1982) Arch. Int. Pharmacodyn. Ther , vol.258 , Issue.171 , pp. 3
    • Gommeren, W.1    Leysen, J.E.2
  • 8
    • 0021863987 scopus 로고
    • Opiate receptors in brain labeled in vivo with [3H]lofentanil
    • Laduron, P.M.; Poncet, J.; Janssen, P.F. Opiate receptors in brain labeled in vivo with [3H]lofentanil. Neuropharmacology, 1985, 24, 617-20.
    • (1985) Neuropharmacology , vol.24 , pp. 617-620
    • Laduron, P.M.1    Poncet, J.2    Janssen, P.F.3
  • 10
    • 0022972078 scopus 로고
    • Synthetic 1,4- disubstituted-1,4-dihydro-5H-tetrazol-5-one derivatives of fentanyl: Alfentanil (R 39209), a potent, extremely short-acting narcotic analgesic
    • Janssens, F.; Torremans, J.; Janssen, P.A. Synthetic 1,4- disubstituted-1,4-dihydro-5H-tetrazol-5-one derivatives of fentanyl: alfentanil (R 39209), a potent, extremely short-acting narcotic analgesic. J. Med. Chem., 1986, 29, 2290-7.
    • (1986) J. Med. Chem , vol.29 , pp. 2290-2297
    • Janssens, F.1    Torremans, J.2    Janssen, P.A.3
  • 12
    • 4644343161 scopus 로고    scopus 로고
    • Multiple opiate receptors:dE'ja' vu all over again
    • Pasternak, G.W. Multiple opiate receptors:dE'ja' vu all over again. Neuropharmacology, 2004, 47, 312-23.
    • (2004) Neuropharmacology , vol.47 , pp. 312-323
    • Pasternak, G.W.1
  • 13
    • 6844254562 scopus 로고    scopus 로고
    • 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. Opioid peptide receptor studies. 7. The methylfentanyl congener RTI-4614-4 and its four enantiomers bind to different domains of the rat mu opioid receptor. Synapse, 1998, 28, 117-24.
    • 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. Opioid peptide receptor studies. 7. The methylfentanyl congener RTI-4614-4 and its four enantiomers bind to different domains of the rat mu opioid receptor. Synapse, 1998, 28, 117-24.
  • 14
    • 0033529014 scopus 로고    scopus 로고
    • Emerging molecular approaches to pain therapy
    • Williams, M.; Kowaluk, E.A; Arneric, S.P. Emerging molecular approaches to pain therapy. J. Med. Chem., 1999, 42, 1481-500.
    • (1999) J. Med. Chem , vol.42 , pp. 1481-1500
    • Williams, M.1    Kowaluk, E.A.2    Arneric, S.P.3
  • 15
    • 0034628575 scopus 로고    scopus 로고
    • Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor
    • Subramanian, G.; Paterlini, M.G.; Portoghese, P.S.; Ferguson, D.M. Molecular docking reveals a novel binding site model for fentanyl at the mu-opioid receptor. J. Med. Chem., 2000, 43, 381-91.
    • (2000) J. Med. Chem , vol.43 , pp. 381-391
    • Subramanian, G.1    Paterlini, M.G.2    Portoghese, P.S.3    Ferguson, D.M.4
  • 16
    • 0034719481 scopus 로고    scopus 로고
    • Structural determinants of efficacy for kappa opioid receptors in the orvinol series: 7,7-spiro analogs of buprenorphine
    • Husbands, S.M.; Lewis, J.W. Structural determinants of efficacy for kappa opioid receptors in the orvinol series: 7,7-spiro analogs of buprenorphine. J. Med. Chem., 2000, 43, 139-41
    • (2000) J. Med. Chem , vol.43 , pp. 139-141
    • Husbands, S.M.1    Lewis, J.W.2
  • 18
    • 33645070773 scopus 로고    scopus 로고
    • Opioid ligands with mixed μ / δ opioid receptor interactions: An emerging approach to novel analgesics
    • Subramaniam, A. Opioid ligands with mixed μ / δ opioid receptor interactions: An emerging approach to novel analgesics. AAPS J., 2006, 8, E118-25.
    • (2006) AAPS J , vol.8
    • Subramaniam, A.1
  • 19
    • 33644982587 scopus 로고    scopus 로고
    • Steric interactions and the activity of fentanyl analogs at the mu-opioid receptor
    • Došen-Mićović, L.; Ivanović, M.; Mićović, V. Steric interactions and the activity of fentanyl analogs at the mu-opioid receptor. Bioorg. Med. Chem., 2006, 14, 2887-95.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 2887-2895
    • Došen-Mićović, L.1    Ivanović, M.2    Mićović, V.3
  • 20
    • 33947596846 scopus 로고    scopus 로고
    • Understanding the structural requirements of 4-anilidopiperidine analogs for biological activities at μ and δ opioid receptors
    • Lee, Y.S.; Nyberg, J.; Moye, S.; Agnes, R.S.; Davis, P.; Ma, S-w; Lai, J; Porreca, F.; Vardanyana, H.V.J. Understanding the structural requirements of 4-anilidopiperidine analogs for biological activities at μ and δ opioid receptors. Bioorg. Med. Chem. Lett., 2007, 17, 2161-5.
    • (2007) Bioorg. Med. Chem. Lett , vol.17 , pp. 2161-2165
    • Lee, Y.S.1    Nyberg, J.2    Moye, S.3    Agnes, R.S.4    Davis, P.5    Ma, S.-W.6    Lai, J.7    Porreca, F.8    Vardanyana, H.V.J.9
  • 21
    • 1542603189 scopus 로고    scopus 로고
    • In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor
    • Jewett, DM.; Kilbourn, M.R. In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor. Nucl. Med. Biol., 2004, 31, 321-5.
    • (2004) Nucl. Med. Biol , vol.31 , pp. 321-325
    • Jewett, D.M.1    Kilbourn, M.R.2
  • 23
    • 28144452230 scopus 로고    scopus 로고
    • Syntheses, biological evaluation, and molecular modeling of 18F-labeled 4-anilidopiperidines as mu-opioid receptor imaging agents
    • Lavecchia, A.; Novellino, E.; Wester, H.J. Syntheses, biological evaluation, and molecular modeling of 18F-labeled 4-anilidopiperidines as mu-opioid receptor imaging agents. J. Med. Chem., 2005, 48, 7720-32.
    • (2005) J. Med. Chem , vol.48 , pp. 7720-7732
    • Lavecchia, A.1    Novellino, E.2    Wester, H.J.3
  • 24
    • 0036805265 scopus 로고    scopus 로고
    • Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET)
    • Bencherif, B.; Fuchs, P.N.; Sheth, R.; Dannals, R.F.; Campbell, J.N.; Frost, J.J. Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET). Pain, 2002, 99, 589-98.
    • (2002) Pain , vol.99 , pp. 589-598
    • Bencherif, B.1    Fuchs, P.N.2    Sheth, R.3    Dannals, R.F.4    Campbell, J.N.5    Frost, J.J.6
  • 26
    • 0021984318 scopus 로고
    • Opioid control of the function of primary afferent substance P fibres
    • Lembeck, F.; Donnerer, J. Opioid control of the function of primary afferent substance P fibres. Eur. J. Pharmacol., 1985, 114, 241-6.
    • (1985) Eur. J. Pharmacol , vol.114 , pp. 241-246
    • Lembeck, F.1    Donnerer, J.2
  • 27
  • 28
    • 0015634428 scopus 로고
    • 4-Anilidopiperidine analgesics. I. Synthesis and analgesic activity of certain ring-methylated 1-substituted 4-propananilidopiperidines
    • Riley, T.N.; Hale, D.B.; Wilson, M.C. 4-Anilidopiperidine analgesics. I. Synthesis and analgesic activity of certain ring-methylated 1-substituted 4-propananilidopiperidines. J. Pharm. Sci., 1973, 62, 983-6.
    • (1973) J. Pharm. Sci , vol.62 , pp. 983-986
    • Riley, T.N.1    Hale, D.B.2    Wilson, M.C.3
  • 29
    • 0017062554 scopus 로고
    • N-4-Substituted 1-(2-arylethyl)-4-piperidinyl-N-phenylpropanamides, a novel series of extremely potent analgesics with unusually high safety margin
    • Van Bever, W.F.; Niemegeers, C.J.; Schellekens, K.H.; Janssen, P.A. N-4-Substituted 1-(2-arylethyl)-4-piperidinyl-N-phenylpropanamides, a novel series of extremely potent analgesics with unusually high safety margin. Arzneimittelforschung, 1976, 26, 1548-51
    • (1976) Arzneimittelforschung , vol.26 , pp. 1548-1551
    • Van Bever, W.F.1    Niemegeers, C.J.2    Schellekens, K.H.3    Janssen, P.A.4
  • 30
    • 0018669470 scopus 로고    scopus 로고
    • Riley, T.N.; Bagley, J.R. 4-Anilidopiperidine analgesics. 2. A study of the conformational aspects of the analgesic activity of the 4-anilidopiperidines utilizing isomeric N-substituted 3-(propananilido)nortropane analogs. J. Med. Chem., 1979, 22, 1167-71.
    • Riley, T.N.; Bagley, J.R. 4-Anilidopiperidine analgesics. 2. A study of the conformational aspects of the analgesic activity of the 4-anilidopiperidines utilizing isomeric N-substituted 3-(propananilido)nortropane analogs. J. Med. Chem., 1979, 22, 1167-71.
  • 31
    • 0018822859 scopus 로고
    • 4-Anilidopiperidine analgesics. 3. 1-Substituted 4-(propananilido)perhydroazepines as ring-expanded analogs
    • Finney, Z.G., Riley, T.N. 4-Anilidopiperidine analgesics. 3. 1-Substituted 4-(propananilido)perhydroazepines as ring-expanded analogs. J. Med. Chem., 1980, 23, 895-9.
    • (1980) J. Med. Chem , vol.23 , pp. 895-899
    • Finney, Z.G.1    Riley, T.N.2
  • 32
    • 0023688539 scopus 로고
    • Structure-activity studies of fentanyl
    • Casy, A.F.; Huckstep, M.R. Structure-activity studies of fentanyl. J. Pharm. Pharmacol., 1988, 40, 605-8.
    • (1988) J. Pharm. Pharmacol , vol.40 , pp. 605-608
    • Casy, A.F.1    Huckstep, M.R.2
  • 34
    • 0024311158 scopus 로고    scopus 로고
    • Kudzma, L.V.; Severnak, S.A.; Benvenga, M.J.; Ezell, E.F.; Ossipov, M.H.; Knight, V.V,; Rudo, F.G.; Spencer, H.K.; Spaulding, T.C. 4-Phenyl- and 4-heteroaryl-4-anilidopiperidines. A novel class of analgesic and anesthetic agents. J. Med. Chem., 1989, 32, 2534- 2.
    • Kudzma, L.V.; Severnak, S.A.; Benvenga, M.J.; Ezell, E.F.; Ossipov, M.H.; Knight, V.V,; Rudo, F.G.; Spencer, H.K.; Spaulding, T.C. 4-Phenyl- and 4-heteroaryl-4-anilidopiperidines. A novel class of analgesic and anesthetic agents. J. Med. Chem., 1989, 32, 2534- 2.
  • 36
    • 0025121178 scopus 로고
    • Synthesis and pharmacological evaluation of a series of new 3-methyl-1,4-disubstituted-piperidine analgesics
    • Lalinde, N.; Moliterni, J.; Wright, D.; Spencer, H.K.; Ossipov, M.H.; Spaulding, T.C.; Rudo, F.G. Synthesis and pharmacological evaluation of a series of new 3-methyl-1,4-disubstituted-piperidine analgesics. J. Med. Chem., 1990, 33, 2876-82.
    • (1990) J. Med. Chem , vol.33 , pp. 2876-2882
    • Lalinde, N.1    Moliterni, J.2    Wright, D.3    Spencer, H.K.4    Ossipov, M.H.5    Spaulding, T.C.6    Rudo, F.G.7
  • 38
    • 0024507397 scopus 로고
    • New 4-(heteroanilido)piperidines, structurally related to the pure opioid agonist fentanyl, with agonist and/or antagonist properties
    • Bagley, J.R.; Wynn, R.L.; Rudo, F.G.; Doorley, B.M.; Spencer, H.K.; Spaulding, T. New 4-(heteroanilido)piperidines, structurally related to the pure opioid agonist fentanyl, with agonist and/or antagonist properties. J. Med. Chem., 1989, 32, 663-71.
    • (1989) J. Med. Chem , vol.32 , pp. 663-671
    • Bagley, J.R.1    Wynn, R.L.2    Rudo, F.G.3    Doorley, B.M.4    Spencer, H.K.5    Spaulding, T.6
  • 46
    • 11844265914 scopus 로고    scopus 로고
    • Using support vector classification for SAR of fentanyl derivatives
    • Dong, N.; Lu, W.C.; Chen, N.Y.; Zhu, Y.C.; Chen, K.X.Using support vector classification for SAR of fentanyl derivatives. Acta Pharmacol. Sin., 2005, 26, 107-12.
    • (2005) Acta Pharmacol. Sin , vol.26 , pp. 107-112
    • Dong, N.1    Lu, W.C.2    Chen, N.Y.3    Zhu, Y.C.4    Chen, K.X.5
  • 47
    • 52049117377 scopus 로고    scopus 로고
    • Analgesic activity and pharmacological characterization of N- [1-phenylpyrazol]-3-yl-N-1-(2-phenethyl)-4-piperidylpropenamide, a new opioid agonist acting peripherally
    • Goicoechea, C.; SÃnchez, E.; Cano, C.; Jagerovic, N.; MartÃn, M.I. Analgesic activity and pharmacological characterization of N- [1-phenylpyrazol]-3-yl-N-1-(2-phenethyl)-4-piperidylpropenamide, a new opioid agonist acting peripherally. Eur. J. Pharmacol., 2008, 24, 595, 22-9.
    • (2008) Eur. J. Pharmacol , vol.24 , Issue.595 , pp. 22-29
    • Goicoechea, C.1    SÃnchez, E.2    Cano, C.3    Jagerovic, N.4    MartÃn, M.I.5
  • 48
    • 0016245082 scopus 로고
    • Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-(3-methyl-1-(2-phenylethyl)-4-piperidyl)-N-phenylpropanamide and N-(3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl)-N-phenylpropanamide
    • Van Bever, W.F.; Niemegeers, C.J.; Janssen, P.A. Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-(3-methyl-1-(2-phenylethyl)-4-piperidyl)-N-phenylpropanamide and N-(3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl)-N-phenylpropanamide. J. Med. Chem., 1974, 17, 1047-51.
    • (1974) J. Med. Chem , vol.17 , pp. 1047-1051
    • Van Bever, W.F.1    Niemegeers, C.J.2    Janssen, P.A.3
  • 51
    • 0025695025 scopus 로고
    • The potent opioid agonist, (+)-cis-3-methylfentanyl binds pseudoirreversibly to the opioid receptor complex in vitro and in vivo: Evidence for a novel mechanism of action
    • Band, L.; Xu, H.; Bykov, V.; Greig, N.; Kim, C.H.; Newman, A.; Jacobson, A.E.; Rice, K.C.; Rothman, R.B. The potent opioid agonist, (+)-cis-3-methylfentanyl binds pseudoirreversibly to the opioid receptor complex in vitro and in vivo: Evidence for a novel mechanism of action. Life Sci., 1990, 47, 2231-40.
    • (1990) Life Sci , vol.47 , pp. 2231-2240
    • Band, L.1    Xu, H.2    Bykov, V.3    Greig, N.4    Kim, C.H.5    Newman, A.6    Jacobson, A.E.7    Rice, K.C.8    Rothman, R.B.9
  • 52
    • 0025858946 scopus 로고
    • (+)-cis-3-Methylfentanyl and its analogs bind pseudoirreversibly to the mu opioid binding site: Evidence for pseudoallosteric modulation
    • Xu, H.; Kim, C-H.; Zhu, Y.C.; Weber, R.J.; Jacobson, A.E.; Rice, K.C.; Rothman, R.B. (+)-cis-3-Methylfentanyl and its analogs bind pseudoirreversibly to the mu opioid binding site: Evidence for pseudoallosteric modulation. Neuropharmacology, 1991, 3, 455-62.
    • (1991) Neuropharmacology , vol.3 , pp. 455-462
    • Xu, H.1    Kim, C.-H.2    Zhu, Y.C.3    Weber, R.J.4    Jacobson, A.E.5    Rice, K.C.6    Rothman, R.B.7
  • 53
    • 0027368964 scopus 로고
    • Stereochemical requirements for pseudoirreversible inhibition of opioid mu receptor binding by the 3-methylfentanyl congeners, RTI-46144 and its enantiomers: Evidence for different binding domains
    • Ni, Q.; Xu, H.; Partilla, J.S.; Stark, P.A.; Carroll, F.I.; Brine, G.A.; Rothman, R.B. Stereochemical requirements for pseudoirreversible inhibition of opioid mu receptor binding by the 3-methylfentanyl congeners, RTI-46144 and its enantiomers: Evidence for different binding domains. Synapse, 1993, 15, 296-306.
    • (1993) Synapse , vol.15 , pp. 296-306
    • Ni, Q.1    Xu, H.2    Partilla, J.S.3    Stark, P.A.4    Carroll, F.I.5    Brine, G.A.6    Rothman, R.B.7
  • 54
    • 0017756322 scopus 로고
    • Agonist and antagonist properties of buprenorphine, a new antinociceptive agent
    • Cowan, A.; Lewis, J.W.; Macfarlane, I.R. Agonist and antagonist properties of buprenorphine, a new antinociceptive agent. Br. J. Pharmacol., 1977, 60, 537-45.
    • (1977) Br. J. Pharmacol , vol.60 , pp. 537-545
    • Cowan, A.1    Lewis, J.W.2    Macfarlane, I.R.3
  • 55
    • 38449088474 scopus 로고    scopus 로고
    • Naloxone reversal of opioid-induced respiratory depression with special emphasis on the partial agonist/ antagonist buprenorphine
    • Sarton, E.; Teppema, L.; Dahan, A. Naloxone reversal of opioid-induced respiratory depression with special emphasis on the partial agonist/ antagonist buprenorphine. Adv. Exp. Med. Biol., 2008, 605, 486-91.
    • (2008) Adv. Exp. Med. Biol , vol.605 , pp. 486-491
    • Sarton, E.1    Teppema, L.2    Dahan, A.3
  • 56
    • 0029820849 scopus 로고    scopus 로고
    • Clinical pharmacokineticsof alfentanil, fentanyl and sufentanil. An update
    • Scholz, J., Steinfath, M.; Schulz, M. Clinical pharmacokineticsof alfentanil, fentanyl and sufentanil. An update. Clin Pharmacokinet., 1996, 31, 275-92.
    • (1996) Clin Pharmacokinet , vol.31 , pp. 275-292
    • Scholz, J.1    Steinfath, M.2    Schulz, M.3
  • 62
    • 70349404532 scopus 로고    scopus 로고
    • The effects of 3-carbomethoxy fentanyl on body temperature in rats. The 5th Congress of the European Association for Clinical Pharmacology and Therapeutics, Odense, Denmark
    • Vučković, S.; Prostran, M.; Ivanović, M.; Todorović, Z.; Stojanović, R.; Nešić, Z.; Milovanović, S. The effects of 3-carbomethoxy fentanyl on body temperature in rats. The 5th Congress of the European Association for Clinical Pharmacology and Therapeutics, Odense, Denmark. Pharmacol. Toxicol., 2001, 89, 98.
    • (2001) Pharmacol. Toxicol , vol.89 , pp. 98
    • Vučković, S.1    Prostran, M.2    Ivanović, M.3    Todorović, Z.4    Stojanović, R.5    Nešić, Z.6    Milovanović, S.7
  • 63
    • 70349404531 scopus 로고    scopus 로고
    • Analgetic and hypertermic effects of 3-butylfentanyl in rats: Structure-activity relationship. The 15th Congress of the European College of Neuropsychopharmacology, Barcelona, Spain
    • Prostran, M.; Vučković, S.; Nešić, Z.; Stojanović, R.; Todorović, Z. Analgetic and hypertermic effects of 3-butylfentanyl in rats: Structure-activity relationship. The 15th Congress of the European College of Neuropsychopharmacology, Barcelona, Spain. Eur. Neuropsychopharmacol., 2002, 12, 428.
    • (2002) Eur. Neuropsychopharmacol , vol.12 , pp. 428
    • Prostran, M.1    Vučković, S.2    Nešić, Z.3    Stojanović, R.4    Todorović, Z.5
  • 64
    • 33750349004 scopus 로고    scopus 로고
    • Managing cancer pain and symptoms of outpatients by rotation to sustained-release hydromorphone: A prospective clinical trial
    • Wirz, S.; Wartenberg, H.C.; Elsen, C.; Wittmann, M.; Diederichs, M.; Nadstawek, J. Managing cancer pain and symptoms of outpatients by rotation to sustained-release hydromorphone: A prospective clinical trial. Clin. J. Pain, 2006, 22, 770-5.
    • (2006) Clin. J. Pain , vol.22 , pp. 770-775
    • Wirz, S.1    Wartenberg, H.C.2    Elsen, C.3    Wittmann, M.4    Diederichs, M.5    Nadstawek, J.6
  • 65
    • 34250175774 scopus 로고    scopus 로고
    • Opioid rotation from high-dose morphine to transdermal buprenorphine (Transtec) in chronic pain patients
    • Freye, E.; Anderson-Hillemacher, A.; Ritzdorf, I.; Levy, J.V. Opioid rotation from high-dose morphine to transdermal buprenorphine (Transtec) in chronic pain patients. Pain Pract., 2007, 7, 123-9.
    • (2007) Pain Pract , vol.7 , pp. 123-129
    • Freye, E.1    Anderson-Hillemacher, A.2    Ritzdorf, I.3    Levy, J.V.4
  • 68
    • 34249080643 scopus 로고    scopus 로고
    • Absence of conditioned place preference or reinstatement with bivalent ligands containing mu-opioid receptor agonist and delta-opioid receptor antagonist pharmacophores
    • Lenard, N.R.; Daniels, D.J.; Portoghese, P.S.; Roerig, S.C. Absence of conditioned place preference or reinstatement with bivalent ligands containing mu-opioid receptor agonist and delta-opioid receptor antagonist pharmacophores. Eur. J. Pharmacol., 2007 566, 75-82.
    • (2007) Eur. J. Pharmacol , vol.566 , pp. 75-82
    • Lenard, N.R.1    Daniels, D.J.2    Portoghese, P.S.3    Roerig, S.C.4
  • 69
    • 30044442319 scopus 로고    scopus 로고
    • Opioid-induced tolerance and dependence in mice is modulated by the distance between pharmacophores in a bivalent ligand series
    • Daniels, D.J.; Lenard, N.R.; Etienne, C.L.; Law, P.Y.; Roerig, S.C.; Portoghese, P.S. Opioid-induced tolerance and dependence in mice is modulated by the distance between pharmacophores in a bivalent ligand series. Proc. Natl. Acad. Sci. U.S.A., 2005, 102, 19208-13.
    • (2005) Proc. Natl. Acad. Sci. U.S.A , vol.102 , pp. 19208-19213
    • Daniels, D.J.1    Lenard, N.R.2    Etienne, C.L.3    Law, P.Y.4    Roerig, S.C.5    Portoghese, P.S.6


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