메뉴 건너뛰기




Volumn 43, Issue 15, 2000, Pages 2922-2928

ElogP(oct): A tool for lipophilicity determination in drug discovery

Author keywords

[No Author keywords available]

Indexed keywords

6 METHYLTHIOINOSINE; ACETOPHENONE; ALLOPURINOL; BIFONAZOLE; BROMAZEPAM; CAFFEINE; CARBAMAZEPINE; CLOTRIMAZOLE; DEXAMETHASONE; DIAZEPAM; DIETHYLSTILBESTROL; DRUG; ESTRADIOL; FLUCONAZOLE; GRISEOFULVIN; HYDROCORTISONE; HYDROCORTISONE ACETATE; LORAZEPAM; LORMETAZEPAM; NAPHTHALENE; NIFEDIPINE; NIFUROXIME; PARACETAMOL; PHENAZONE; PHENOL DERIVATIVE; PREDNISOLONE; PREDNISONE; QUINOLINE DERIVATIVE; TESTOSTERONE; TOLNAFTATE; UNINDEXED DRUG; OCTANOL; SOLVENT;

EID: 0034720879     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0000822     Document Type: Article
Times cited : (228)

References (37)
  • 1
    • 0019166075 scopus 로고
    • Solubility and partitioning I: Solubility of nonelectrolytes in water
    • Yalkowski, S. H.; Valvani, S. C. Solubility and Partitioning I: Solubility of Nonelectrolytes in Water. J. Pharm. Sci. 1980, 69, 912-922.
    • (1980) J. Pharm. Sci. , vol.69 , pp. 912-922
    • Yalkowski, S.H.1    Valvani, S.C.2
  • 2
    • 0029865450 scopus 로고    scopus 로고
    • Design of drugs involving the concepts and theories of drug metabolism and pharmacokinetics
    • Smith, D. A.; Jones, B. C.; Walker, D. K. Design of Drugs Involving the Concepts and Theories of Drug Metabolism and Pharmacokinetics. Med. Res. Rev. 1996, 16, 243-266.
    • (1996) Med. Res. Rev. , vol.16 , pp. 243-266
    • Smith, D.A.1    Jones, B.C.2    Walker, D.K.3
  • 3
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development. Adv. Drug. Del. Rev. 1997, 23, 3-25.
    • (1997) Adv. Drug. Del. Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 5
    • 84958623621 scopus 로고    scopus 로고
    • Lipophilicity measurements by reversed-phase high performance liquid chromatography (RP-HPLC)
    • Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH: Weinheim, Chapter 5
    • van de Waterbeemd, H. M.; Kansy, M.; Wagner, B.; Fischer, H. Lipophilicity Measurements by Reversed-Phase High Performance Liquid Chromatography (RP-HPLC). In Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH: Weinheim, 1996; Chapter 5, pp 73-87.
    • (1996) Lipophilicity in Drug Action and Toxicology , pp. 73-87
    • Van De Waterbeemd, H.M.1    Kansy, M.2    Wagner, B.3    Fischer, H.4
  • 6
    • 0029032040 scopus 로고
    • Structural properties governing retention mechanisms on RP-HPLC stationary phases used for lipophilicity measurements
    • Pagliara, A.; Khamis, E.; Trinh, A.; Carrupt, P.-A.; Tsai, R.-S.; Testa, B. Structural Properties Governing Retention Mechanisms on RP-HPLC Stationary Phases used for Lipophilicity Measurements. J. Liq. Chromatogr. 1995, 18, 1721-1745.
    • (1995) J. Liq. Chromatogr. , vol.18 , pp. 1721-1745
    • Pagliara, A.1    Khamis, E.2    Trinh, A.3    Carrupt, P.-A.4    Tsai, R.-S.5    Testa, B.6
  • 7
    • 0023730309 scopus 로고
    • A comprehensive method for determining hydrophobicity constants by reversed-phase high-performance liquid chromatography
    • Minick, D. J.; Frenz, J. H.; Patrick, M. A.; Brent, D. A. A Comprehensive Method for Determining Hydrophobicity Constants by Reversed-Phase High-Performance Liquid Chromatography. J. Med. Chem. 1988, 31, 1923-1933.
    • (1988) J. Med. Chem. , vol.31 , pp. 1923-1933
    • Minick, D.J.1    Frenz, J.H.2    Patrick, M.A.3    Brent, D.A.4
  • 8
    • 0028340366 scopus 로고
    • Estimation and correlation of drug water solubility with pharmacological parameters required for biological activity
    • Morelock, M. M.; Choi, L. L.; Bell, G. L.; Wright, J. L. Estimation and Correlation of Drug Water Solubility with Pharmacological Parameters Required for Biological Activity. J. Pharm. Sci. 1994, 83, 948-952.
    • (1994) J. Pharm. Sci. , vol.83 , pp. 948-952
    • Morelock, M.M.1    Choi, L.L.2    Bell, G.L.3    Wright, J.L.4
  • 9
    • 0027941950 scopus 로고
    • Hydrogen bonding. 35. Relationship between high-performance liquid chromatography capacity factors and water-octanol partition coefficients
    • Abraham, M. H.; Chadha, H. S.; Leo, A. J. Hydrogen Bonding. 35. Relationship between high-performance liquid chromatography capacity factors and water-octanol partition coefficients. J. Chromatogr. A 1994, 685, 203-211.
    • (1994) J. Chromatogr. A , vol.685 , pp. 203-211
    • Abraham, M.H.1    Chadha, H.S.2    Leo, A.J.3
  • 10
    • 0032732592 scopus 로고    scopus 로고
    • Measurement and prediction of hydrophobicity parameters for highly lipophilic compounds: Application of the HPLC column-switching technique to measurement of logP of diarylpyrazines
    • Yamagami, C.; Araki, K.; Ohnishi, K.; Hanasato, K.; Inaba, H.; Aono, M.; Ohta, A. Measurement and Prediction of Hydrophobicity Parameters for Highly Lipophilic Compounds: Application of the HPLC Column-Switching Technique to Measurement of logP of Diarylpyrazines. J. Pharm. Sci. 1999, 88, 1299-1304.
    • (1999) J. Pharm. Sci. , vol.88 , pp. 1299-1304
    • Yamagami, C.1    Araki, K.2    Ohnishi, K.3    Hanasato, K.4    Inaba, H.5    Aono, M.6    Ohta, A.7
  • 11
    • 0000795719 scopus 로고
    • Hydrophobic properties of drugs
    • Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford
    • Taylor, P. J. Hydrophobic Properties of Drugs. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: Oxford, 1990; Vol. 5, pp 241-294.
    • (1990) Comprehensive Medicinal Chemistry , vol.5 , pp. 241-294
    • Taylor, P.J.1
  • 12
    • 0002690622 scopus 로고
    • Modeling octanol-water partition coefficients by reversed-phase liquid chromatography
    • Minick, D. J.; Brent, D. A.; Frenz, J. Modeling Octanol-Water Partition Coefficients by Reversed-Phase Liquid Chromatography. J. Chromatogr. 1989, 461, 177-191.
    • (1989) J. Chromatogr. , vol.461 , pp. 177-191
    • Minick, D.J.1    Brent, D.A.2    Frenz, J.3
  • 13
    • 0342293781 scopus 로고    scopus 로고
    • note
    • The LC-ABZ column is considered to be "RP-18 like", and it was described as being electrostatically coated to decrease the solute interactions with free silanols. See ref 6. It is described by the manufacturer as an embedded amide functional group column and as having some polymeric (cross-linking) character and multiple points of attachment to the silica surface.
  • 14
    • 8244253850 scopus 로고
    • Stationary phase effects in reversed-phase chromatography. I. Comparison of energetics of retention on alkyl-silica bonded phases
    • Melander, W.; Stoveken, J.; Horvath, C. Stationary Phase Effects in Reversed-Phase Chromatography. I. Comparison of Energetics of Retention on Alkyl-Silica Bonded Phases. J. Chromatogr. 1980, 199, 35-56.
    • (1980) J. Chromatogr. , vol.199 , pp. 35-56
    • Melander, W.1    Stoveken, J.2    Horvath, C.3
  • 15
    • 0000607945 scopus 로고    scopus 로고
    • Chromatographic hydrophobicity index by fast-gradient RP-HPLC: A high-throughput alternative to logP/logD
    • Valko K.; Bevan, C.; Reynolds, D. Chromatographic Hydrophobicity Index by Fast-Gradient RP-HPLC: A High-Throughput Alternative to logP/logD. Anal. Chem. 1997, 69, 2022-2029.
    • (1997) Anal. Chem. , vol.69 , pp. 2022-2029
    • Valko, K.1    Bevan, C.2    Reynolds, D.3
  • 16
    • 12044255753 scopus 로고
    • Scales of solute hydrogen-bonding; their construction and application to physicochemical and biochemical processes
    • (a) Abraham, M. H. Scales of Solute Hydrogen-bonding; Their Construction and Application to Physicochemical and Biochemical Processes. Chem. Soc. Rev. 1993, 22, 73-83.
    • (1993) Chem. Soc. Rev. , vol.22 , pp. 73-83
    • Abraham, M.H.1
  • 17
    • 0030897980 scopus 로고    scopus 로고
    • Determination of solute lipophilicity as logP (octanol) and logP (alkane) using poly-(styrene-divinylbenzene) and immobilised artificial membrane stationary phases in reversed-phase high performance liquid chromatography
    • (b) Abraham, M. H.; Chadha, H. S.; Leitao, R. A. E.; Mitchell, R. C.; Lambert, W. J.; Kaliszan, R.; Nasal, A.; Haber, P. Determination of solute lipophilicity as logP (octanol) and logP (alkane) using poly-(styrene-divinylbenzene) and immobilised artificial membrane stationary phases in reversed-phase high performance liquid Chromatography. J. Cromatogr. A. 1997, 766, 35-47.
    • (1997) J. Cromatogr. A. , vol.766 , pp. 35-47
    • Abraham, M.H.1    Chadha, H.S.2    Leitao, R.A.E.3    Mitchell, R.C.4    Lambert, W.J.5    Kaliszan, R.6    Nasal, A.7    Haber, P.8
  • 18
    • 0027982335 scopus 로고
    • Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the AlogP parameter of Seiler
    • Abraham, M. H.; Chadha, H. S.; Whiting, G. S.; Mitchell, R. C. Hydrogen Bonding. 32. An Analysis of Water-Octanol and Water-Alkane Partitioning and the AlogP Parameter of Seiler. J. Pharm. Sci. 1994, 83, 1085-1100.
    • (1994) J. Pharm. Sci. , vol.83 , pp. 1085-1100
    • Abraham, M.H.1    Chadha, H.S.2    Whiting, G.S.3    Mitchell, R.C.4
  • 19
    • 0028058951 scopus 로고
    • pH-metric log P. 4. Comparison of partition coefficients determined by HPLC and potentiometric methods to literature values
    • Slater, B.; McCormack, A.; Avdeef, A.; Comer, J. E. A. pH-Metric log P. 4. Comparison of Partition Coefficients Determined by HPLC and Potentiometric Methods to Literature Values. J. Pharm. Sci. 1994, 83, 1280-1283.
    • (1994) J. Pharm. Sci. , vol.83 , pp. 1280-1283
    • Slater, B.1    McCormack, A.2    Avdeef, A.3    Comer, J.E.A.4
  • 20
    • 0028206698 scopus 로고
    • Fluconazole: Interspecies scaling and allometric relationships of pharmacokinetic properties
    • Jezequel, S. G. Fluconazole: interspecies scaling and allometric relationships of pharmacokinetic properties. J. Pharm. Pharmacol. 1994, 46, 196-199.
    • (1994) J. Pharm. Pharmacol. , vol.46 , pp. 196-199
    • Jezequel, S.G.1
  • 21
    • 33749000228 scopus 로고
    • A new substituent constant, π, derived from partition coefficients
    • Fujita, T.; Iwasa, J.; Hansh, C. A new substituent constant, π, derived from partition coefficients. J. Am. Chem. Soc. 1965, 86, 5175-5180.
    • (1965) J. Am. Chem. Soc. , vol.86 , pp. 5175-5180
    • Fujita, T.1    Iwasa, J.2    Hansh, C.3
  • 22
    • 84990678804 scopus 로고
    • Relationship between octanol-water partition data, chromatographic indices and their dependence on pH in a set of nonsteroidal antiinflammatory drugs
    • LaRotonda, M. I.; Amato, G.; Barbato, F.; Silipo, C.; Vittoria, A. Relationship between Octanol-Water partition Data, Chromatographic Indices and their Dependence on pH in a Set of Nonsteroidal Antiinflammatory Drugs. Quant. Struct. Act. Relat. 1983, 2, 168-173.
    • (1983) Quant. Struct. Act. Relat. , vol.2 , pp. 168-173
    • LaRotonda, M.I.1    Amato, G.2    Barbato, F.3    Silipo, C.4    Vittoria, A.5
  • 23
    • 0021885175 scopus 로고
    • Allopurinol prodrugs. II. Synthesis, hydrolysis kinetics and physicochemical properties of various N-acyloxylmethyl allopurinol derivatives
    • Bundgaard, H.; Falch, E. Allopurinol prodrugs. II. Synthesis, hydrolysis kinetics and physicochemical properties of various N-acyloxylmethyl allopurinol derivatives. Int. J. Pharm. 1985, 24, 307-325.
    • (1985) Int. J. Pharm. , vol.24 , pp. 307-325
    • Bundgaard, H.1    Falch, E.2
  • 24
    • 0021246362 scopus 로고
    • The affinities of benzodiazepines to the transport protein of glucose in human erythrocytes
    • The reported value for bromazepam is an average of the values reported by the following authors: (a) Lacko, L.; Wittke, B. The affinities of benzodiazepines to the transport protein of glucose in human erythrocytes. Arzneim.-Forsch. 1984, 34, 403-407.
    • (1984) Arzneim.-Forsch. , vol.34 , pp. 403-407
    • Lacko, L.1    Wittke, B.2
  • 25
    • 0344680362 scopus 로고
    • Interaction of benzodiazepines with human serum albumin. Circular dichroism studies
    • (b) Muller, W.; Wollert, U. Interaction of Benzodiazepines with Human Serum Albumin. Circular Dichroism Studies. Arch. Pharmacol. 1973, 278, 301-312.
    • (1973) Arch. Pharmacol. , vol.278 , pp. 301-312
    • Muller, W.1    Wollert, U.2
  • 26
    • 0028903677 scopus 로고
    • Determination of octanol-water partition coefficients by an HPLC method for anticonvulsant structure-activity studies
    • Henczi, M.; Nagy, J.; Weaver, D. F. Determination of octanol-water partition coefficients by an HPLC method for anticonvulsant structure-activity studies. J. Pharm. Pharmacol. 1995, 47, 345-347.
    • (1995) J. Pharm. Pharmacol. , vol.47 , pp. 345-347
    • Henczi, M.1    Nagy, J.2    Weaver, D.F.3
  • 28
    • 0018170598 scopus 로고
    • Solubilization of steroid hormones by polyoxyethylene lauryl ether
    • Tomida, H.; Yotsuyanagi, T.; Ikeda, K. Solubilization of steroid hormones by polyoxyethylene lauryl ether. Chem. Pharm. Bull. 1978, 26, 2832-2837.
    • (1978) Chem. Pharm. Bull. , vol.26 , pp. 2832-2837
    • Tomida, H.1    Yotsuyanagi, T.2    Ikeda, K.3
  • 29
    • 0021062863 scopus 로고
    • 5-phenyl-1,3-dihydro-1,4-benzodi-azepin-2-ones
    • Seiler, P.; Zimmermann, I. 5-phenyl-1,3-dihydro-1,4-benzodi-azepin-2-ones. Arzneim.-Forsch. 1983, 33, 1519-1522.
    • (1983) Arzneim.-Forsch. , vol.33 , pp. 1519-1522
    • Seiler, P.1    Zimmermann, I.2
  • 30
    • 0017691998 scopus 로고
    • pK- and Vk-messungen an benzodiazepinen
    • Graf, E.; El-Menshawy, M. pK- and Vk-messungen an benzodiazepinen. Pharm. Uns. Zeit. 1977, 6, 171-178.
    • (1977) Pharm. Uns. Zeit. , vol.6 , pp. 171-178
    • Graf, E.1    El-Menshawy, M.2
  • 31
    • 0020027173 scopus 로고
    • Screening, detection and biotransformation of Lormetazepam, a new hypnotic agent from the 1,4-benzodiazepine series
    • Schutz, V. H.; Fitz, H. Screening, detection and biotransformation of Lormetazepam, a new hypnotic agent from the 1,4-benzodiazepine series. Arzneim.-Forsch. 1982, 32, 177-183.
    • (1982) Arzneim.-Forsch. , vol.32 , pp. 177-183
    • Schutz, V.H.1    Fitz, H.2
  • 32
    • 0000416040 scopus 로고
    • Substituent constants for aliphatic functions obtained from partition coefficients
    • Iwasa, J.; Fujita, T.; Hansch, C. Substituent constants for aliphatic functions obtained from partition coefficients. J. Med. Chem. 1965, 8, 150-153.
    • (1965) J. Med. Chem. , vol.8 , pp. 150-153
    • Iwasa, J.1    Fujita, T.2    Hansch, C.3
  • 33
    • 0017238778 scopus 로고
    • 13C nuclear magnetic resonance spectra of antipyrine derivatives and their application to Hansch analysis
    • 13C nuclear magnetic resonance spectra of antipyrine derivatives and their application to Hansch analysis. Chem. Pharm. Bull. 1976, 24, 61-71.
    • (1976) Chem. Pharm. Bull. , vol.24 , pp. 61-71
    • Okada, J.1    Esaki, T.2    Fujieda, K.3
  • 34
    • 0018758207 scopus 로고
    • Effect of lipophilicity of nitroamidazoles on radiosensitization of hypoxic bacterial cells in vitro
    • Anderson, R. F.; Patel, K. B. Effect of lipophilicity of nitroamidazoles on radiosensitization of hypoxic bacterial cells in vitro. Br J. Cancer 1979, 39, 705-710.
    • (1979) Br J. Cancer , vol.39 , pp. 705-710
    • Anderson, R.F.1    Patel, K.B.2
  • 36
    • 0015106401 scopus 로고
    • On chemistry and synthesis of 3,7-dimethyl-1-(5-oxo-hexyl)-xanthine
    • Mohler, V. W.; Soder, A. On chemistry and synthesis of 3,7-dimethyl-1-(5-oxo-hexyl)-xanthine. Arzneim.-Forsch. 1971, 21, 1159-1160.
    • (1971) Arzneim.-Forsch. , vol.21 , pp. 1159-1160
    • Mohler, V.W.1    Soder, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.