메뉴 건너뛰기




Volumn 45, Issue 1-2, 2012, Pages 205-210

Lipophilicity of morphine microspecies and their contribution to the lipophilicity profile

Author keywords

Deductive method; Microscopic partition coefficient; Microscopic protonation constant; Morphine; pH potentiometry; Zwitterion lipophilicity

Indexed keywords

AMPHOLYTE; MORPHINE;

EID: 83655163985     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2011.11.007     Document Type: Article
Times cited : (16)

References (30)
  • 1
    • 0031048588 scopus 로고    scopus 로고
    • On the partition of ampholytes: Application to blood-brain distribution
    • DOI 10.1021/js960328j
    • M.H. Abraham, K. Takács-Novák, and R.C. Mitchell On the partition of ampholytes: application to blood-brain distribution J. Pharm. Sci. 86 1997 310 315 (Pubitemid 27113764)
    • (1997) Journal of Pharmaceutical Sciences , vol.86 , Issue.3 , pp. 310-315
    • Abraham, M.H.1    Takacs-Novak, K.2    Mitchell, R.C.3
  • 2
    • 0029911418 scopus 로고    scopus 로고
    • Octanol-, chloroform-, and propylene glycol dipelargonat-water partitioning of morphine-6-glucuronide and other related opiates
    • DOI 10.1021/jm960073m
    • A. Avdeef, D. Barrett, N. Shaw, R. Knaggs, and S. Davis Octanol-, chloroform-, and propylene glycol dipelargonate-water partitioning of morphine-6-glucuronide and other related opiates J. Med. Chem. 39 1996 4377 4381 (Pubitemid 26359394)
    • (1996) Journal of Medicinal Chemistry , vol.39 , Issue.22 , pp. 4377-4381
    • Avdeef, A.1    Barrett, D.A.2    Shaw, P.N.3    Knaggs, R.D.4    Davis, S.S.5
  • 3
    • 0035468033 scopus 로고    scopus 로고
    • Physicochemical profiling
    • A. Avdeef Physicochemical profiling Curr. Top. Med. Chem. 1 2002 277 351
    • (2002) Curr. Top. Med. Chem. , vol.1 , pp. 277-351
    • Avdeef, A.1
  • 4
    • 0000936109 scopus 로고
    • Dissociation constants of polybasic acids and their application to the calculation of molecular dimensions
    • N. Bjerrum Dissociation constants of polybasic acids and their application to the calculation of molecular dimensions Z. Phys. Chem. 106 1923 219 242
    • (1923) Z. Phys. Chem. , vol.106 , pp. 219-242
    • Bjerrum, N.1
  • 5
    • 0034957416 scopus 로고    scopus 로고
    • The apparent lipophilicity of quaternary ammonium ions is influenced by galvani potential difference, not ion-pairing: A cyclic voltammetry study
    • DOI 10.1023/A:1011001914685
    • G. Bouchard, P.A. Carrupt, B. Testa, V. Gobry, and H.H. Girault The apparent lipophilicity of quaternary ammonium ions is influenced by Galvani potential difference, not ion-pairing: a cyclic voltammetry study Pharm. Res. 18 2001 702 708 (Pubitemid 32595802)
    • (2001) Pharmaceutical Research , vol.18 , Issue.5 , pp. 702-708
    • Bouchard, G.1    Carrupt, P.-A.2    Testa, B.3    Gobry, V.4    Girault, H.H.5
  • 6
    • 0033179099 scopus 로고    scopus 로고
    • Combined molecular lipophilicity descriptors and their role in understanding intramolecular effects
    • DOI 10.1016/S1461-5347(99)00180-7, PII S1461534799001807
    • G. Caron, F. Reymond, P.A. Carrupt, H.H. Girault, and B. Testa Combined molecular lipophilicity descriptors and their role in understanding intramolecular effects Pharm. Sci. Technol. Today 2 1999 327 335 (Pubitemid 29378537)
    • (1999) Pharmaceutical Science and Technology Today , vol.2 , Issue.8 , pp. 327-335
    • Caron, G.1    Reymond, F.2    Carrupt, P.-A.3    Girault, H.H.4    Testa, B.5
  • 7
    • 0003114426 scopus 로고    scopus 로고
    • Lipophilicity profiles: Theory and measurement
    • B. Testa, H. van de Waterbeemd, G. Folkers, R. Guy, Wiley-VCH Publishers Zürich
    • J. Comer, and K. Tam Lipophilicity profiles: theory and measurement B. Testa, H. van de Waterbeemd, G. Folkers, R. Guy, Pharmacokinetic Optimization in Drug Research 2001 Wiley-VCH Publishers Zürich 275 304
    • (2001) Pharmacokinetic Optimization in Drug Research , pp. 275-304
    • Comer, J.1    Tam, K.2
  • 8
    • 0030047878 scopus 로고    scopus 로고
    • Partitioning of substituted phenols in liposome-water, biomembrane-water, and octanol-water systems
    • B.I. Escher, and R.P. Schwarzenbach Partitioning of substituted phenols in liposome-water, biomembrane-water, and octanol-water systems Environ. Sci. Technol. 30 1996 260 270
    • (1996) Environ. Sci. Technol. , vol.30 , pp. 260-270
    • Escher, B.I.1    Schwarzenbach, R.P.2
  • 10
    • 0023933037 scopus 로고
    • 1-Octanol-water partition coefficients of the anionic and zwitterionic species of diprotic zwitterionic cephalosporin antibiotics
    • V.P. Irwin, J.M. Quigley, and R.F. Timoney 1-Octanol-water partition coefficients of the anionic and zwitterionic species of diprotic zwitterionic cephalosporin antibiotics Int. J. Pharm. 43 1988 187 188 (Pubitemid 18097542)
    • (1988) International Journal of Pharmaceutics , vol.43 , Issue.1-2 , pp. 187-188
    • Irwin, V.P.1    Quigley, J.M.2    Timoney, R.F.3
  • 11
    • 0025690244 scopus 로고
    • Effect of pH and KCl concentration on the octanol-water distribution of methylanilines
    • C.A. Johnson, and J.C. Westall Effect of pH and KCl concentration on the octanol-water distribution of methylanilines Environ. Sci. Technol. 24 1990 1869 1875
    • (1990) Environ. Sci. Technol. , vol.24 , pp. 1869-1875
    • Johnson, C.A.1    Westall, J.C.2
  • 12
    • 79955599163 scopus 로고    scopus 로고
    • Lipophilicity and its relationship with passive drug permeation
    • X.L. Liu, B. Testa, and A. Fahr Lipophilicity and its relationship with passive drug permeation Pharm. Res. 28 2011 962 977
    • (2011) Pharm. Res. , vol.28 , pp. 962-977
    • Liu, X.L.1    Testa, B.2    Fahr, A.3
  • 13
    • 33646403422 scopus 로고    scopus 로고
    • Ionization, lipophilicity and solubility properties of repaglinide
    • Z. Mandić, and V. Gabelica Ionization, lipophilicity and solubility properties of repaglinide J. Pharm. Biomed. Anal. 41 2006 866 871
    • (2006) J. Pharm. Biomed. Anal. , vol.41 , pp. 866-871
    • Mandić, Z.1    Gabelica, V.2
  • 14
    • 0032751285 scopus 로고    scopus 로고
    • Proton speciation and microspeciation of vinpocetine and related compounds in aqueous and biomimetic media
    • DOI 10.1023/A:1018966318167
    • K. Mazák, A. Nemes, and B. Noszál Proton speciation and microspeciation of vinpocetine and related compounds in aqueous and biomimetic media Pharm. Res. 16 1999 1757 1763 (Pubitemid 29530410)
    • (1999) Pharmaceutical Research , vol.16 , Issue.11 , pp. 1757-1763
    • Mazak, K.1    Nemes, A.2    Noszal, B.3
  • 15
    • 0037683420 scopus 로고    scopus 로고
    • Lipophilicity of vinpocetine and related compounds characterized by reversed-phase thin-layer chromatography
    • DOI 10.1016/S0021-9673(03)00617-4
    • K. Mazák, J. Vámos, A. Nemes, Á. Rácz, and B. Noszál Lipophilicity of vinpocetine and related compounds characterized by reversed-phase thin-layer chromatography J. Chromatogr. A 996 2003 195 203 (Pubitemid 36627805)
    • (2003) Journal of Chromatography A , vol.996 , Issue.1-2 , pp. 195-203
    • Mazak, K.1    Vamos, J.2    Nemes, A.3    Racz, A.4    Noszal, B.5
  • 16
    • 70349134005 scopus 로고    scopus 로고
    • Structural and physicochemical profiling of morphine and related compounds of therapeutic interest
    • K. Mazák, S. Hosztafi, Á. Rácz, and B. Noszál Structural and physicochemical profiling of morphine and related compounds of therapeutic interest Mini Rev. Med. Chem. 9 2009 984 995
    • (2009) Mini Rev. Med. Chem. , vol.9 , pp. 984-995
    • Mazák, K.1    Hosztafi, S.2    Rácz, Á.3    Noszál, B.4
  • 17
    • 65649126038 scopus 로고    scopus 로고
    • Proton speciation and microspeciation of serotonin and 5-hydroxytryptophan
    • K. Mazák, V. Dóczy, J. Kökösi, and B. Noszál Proton speciation and microspeciation of serotonin and 5-hydroxytryptophan Chem. Biodiver. 6 2009 578 590
    • (2009) Chem. Biodiver. , vol.6 , pp. 578-590
    • Mazák, K.1    Dóczy, V.2    Kökösi, J.3    Noszál, B.4
  • 18
    • 80052031997 scopus 로고    scopus 로고
    • Lipophilicity of zwitterions and related species: A new insight
    • K. Mazák, J. Kökösi, and B. Noszál Lipophilicity of zwitterions and related species: a new insight Eur. J. Pham. Sci. 44 2011 68 73
    • (2011) Eur. J. Pham. Sci. , vol.44 , pp. 68-73
    • Mazák, K.1    Kökösi, J.2    Noszál, B.3
  • 21
    • 0008893051 scopus 로고    scopus 로고
    • Electrochemical aspects of drug partitioning
    • B. Testa, H. van de Waterbeemd, G. Folkers, R. Guy, Wiley-VCH Publishers Zürich
    • F. Reymond, V. Gobry, G. Bouchard, and H. Girault Electrochemical aspects of drug partitioning B. Testa, H. van de Waterbeemd, G. Folkers, R. Guy, Pharmacokinetic Optimization in Drug Research 2001 Wiley-VCH Publishers Zürich 327 349
    • (2001) Pharmacokinetic Optimization in Drug Research , pp. 327-349
    • Reymond, F.1    Gobry, V.2    Bouchard, G.3    Girault, H.4
  • 22
    • 7144240619 scopus 로고
    • Acid dissociation constants of morphine
    • G. Schill, and K. Gustavii Acid dissociation constants of morphine Acta Pharm. Suecica 1 1964 24 35
    • (1964) Acta Pharm. Suecica , vol.1 , pp. 24-35
    • Schill, G.1    Gustavii, K.2
  • 25
    • 0030219011 scopus 로고    scopus 로고
    • Interlaboratory study of log P determination by shake-flask and potentiometric methods
    • DOI 10.1016/0731-7085(96)01773-6
    • K. Takács-Novák, and A. Avdeef Interlaboratory study of log P determination by shake-flask and potentiometric methods J. Pharm. Biomed. Anal. 14 1996 1405 1413 (Pubitemid 26279286)
    • (1996) Journal of Pharmaceutical and Biomedical Analysis , vol.14 , Issue.11 , pp. 1405-1413
    • Takacs-Novak, K.1    Avdeef, A.2
  • 26
    • 0032737277 scopus 로고    scopus 로고
    • Ion-pair partition of quaternary ammonium drugs: The influence of counter ions of different lipophilicity, size and flexibility
    • K. Takács-Novák, and Gy. Szász Ion-pair partition of quaternary ammonium drugs: the influence of counter ions of different lipophilicity, size and flexibility Pharm. Res. 16 1999 1633 1638
    • (1999) Pharm. Res. , vol.16 , pp. 1633-1638
    • Takács-Novák, K.1    Szász, Gy.2
  • 28
    • 0002368625 scopus 로고    scopus 로고
    • Intramolecular interactions encoded in lipophilicity: Their nature and significance
    • V. Pliska, B. Testa, H. van de Waterbeems, VCH Publishers Weinheim
    • B. Testa, P.A. Carrupt, P. Gaillard, and R.S. Tsai Intramolecular interactions encoded in lipophilicity: their nature and significance V. Pliska, B. Testa, H. van de Waterbeems, Lipophilicity in Drug Action and Toxicology 1996 VCH Publishers Weinheim 49 71
    • (1996) Lipophilicity in Drug Action and Toxicology , pp. 49-71
    • Testa, B.1    Carrupt, P.A.2    Gaillard, P.3    Tsai, R.S.4
  • 30
    • 84856164246 scopus 로고    scopus 로고
    • Opioids, analgesia and pain management
    • L.L. Brunton, B.A. Chabner, B.C. Knollmann, McGraw-Hill Medical
    • T.L. Yaksh, and M.S. Wallace Opioids, analgesia and pain management L.L. Brunton, B.A. Chabner, B.C. Knollmann, Goodman & Gilman's The Pharmaceutical Basis of Therapeutics 2010 McGraw-Hill Medical 481 527
    • (2010) Goodman & Gilman's the Pharmaceutical Basis of Therapeutics , pp. 481-527
    • Yaksh, T.L.1    Wallace, M.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.