메뉴 건너뛰기




Volumn 59, Issue 7, 2007, Pages 568-590

Solubility of sparingly-soluble ionizable drugs

Author keywords

Aggregation; Complexation; Dissolution template titration method; Micro dissolution method; Miniaturized shake flask method; pH dependent solubility; Shake flask method; Solubility equations; Sparingly soluble ionizable compounds

Indexed keywords

AGGLOMERATION; COMPLEXATION; COMPUTATIONAL METHODS; DISSOLUTION; IONIZATION; PH EFFECTS; SOLUBILITY; TITRATION;

EID: 34548039925     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.addr.2007.05.008     Document Type: Review
Times cited : (254)

References (88)
  • 1
    • 27644595841 scopus 로고    scopus 로고
    • Aqueous and cosolvent solubility data for drug-like organic compounds
    • Rytting E., Lentz K.A., Chen X.-Q., Qian F., and Venkatesh S. Aqueous and cosolvent solubility data for drug-like organic compounds. The AAPS J. 7 (2005) E78-E105
    • (2005) The AAPS J. , vol.7
    • Rytting, E.1    Lentz, K.A.2    Chen, X.-Q.3    Qian, F.4    Venkatesh, S.5
  • 3
    • 0032841864 scopus 로고    scopus 로고
    • The correlation and prediction of the solubility of compounds in water using an amended solvation energy relationship
    • Abraham M.H., and Le J. The correlation and prediction of the solubility of compounds in water using an amended solvation energy relationship. J. Pharm. Sci. 88 (1999) 868-880
    • (1999) J. Pharm. Sci. , vol.88 , pp. 868-880
    • Abraham, M.H.1    Le, J.2
  • 10
    • 0001056344 scopus 로고    scopus 로고
    • Preparation of water-soluble compounds through salt formation
    • Wermuth C.G. (Ed), Academic Press, London
    • Anderson B.D., and Flora K.P. Preparation of water-soluble compounds through salt formation. In: Wermuth C.G. (Ed). The Practice of Medicinal Chemistry (1996), Academic Press, London 739-754
    • (1996) The Practice of Medicinal Chemistry , pp. 739-754
    • Anderson, B.D.1    Flora, K.P.2
  • 12
    • 84890605478 scopus 로고    scopus 로고
    • Salt selection
    • Hilfiker R. (Ed), Wiley-VCH, Weinheim
    • Stahl P.H. Salt selection. In: Hilfiker R. (Ed). Polymorphism in pharmaceutical industry (2006), Wiley-VCH, Weinheim 309-322
    • (2006) Polymorphism in pharmaceutical industry , pp. 309-322
    • Stahl, P.H.1
  • 13
    • 0030944059 scopus 로고    scopus 로고
    • Spectral methods for the characterization of polymorphs and solvates
    • Brittain H.G. Spectral methods for the characterization of polymorphs and solvates. J. Pharm. Sci. 86 (1997) 405-411
    • (1997) J. Pharm. Sci. , vol.86 , pp. 405-411
    • Brittain, H.G.1
  • 14
  • 15
    • 0030638567 scopus 로고    scopus 로고
    • Characterization and significance of the amorphous state in pharmaceutical systems
    • Hancock B.C., and Zografi G. Characterization and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci. 86 (1997) 1-12
    • (1997) J. Pharm. Sci. , vol.86 , pp. 1-12
    • Hancock, B.C.1    Zografi, G.2
  • 16
    • 1242337285 scopus 로고    scopus 로고
    • Solubilizing excipients in oral and injectable formulations
    • Strickley R.G. Solubilizing excipients in oral and injectable formulations. Pharm. Res. 21 (2004) 201-230
    • (2004) Pharm. Res. , vol.21 , pp. 201-230
    • Strickley, R.G.1
  • 18
    • 0035468033 scopus 로고    scopus 로고
    • Physicochemical profiling (solubility, permeability, and charge state)
    • Avdeef A. Physicochemical profiling (solubility, permeability, and charge state). Curr. Top. Med. Chem. 1 (2001) 277-351
    • (2001) Curr. Top. Med. Chem. , vol.1 , pp. 277-351
    • Avdeef, A.1
  • 19
    • 34548020576 scopus 로고    scopus 로고
    • Dissolution-solubility: pH, buffer, salt, dual-solid, and aggregation effects
    • Testa B., and van de Waterbeemd H. (Eds), ADME-TOX Approaches, Elsevier, Oxford, UK
    • Avdeef A., Voloboy D., and Foreman A. Dissolution-solubility: pH, buffer, salt, dual-solid, and aggregation effects. In: Testa B., and van de Waterbeemd H. (Eds). Comprehensive medicinal chemistry II Vol. 5 (2007), ADME-TOX Approaches, Elsevier, Oxford, UK 399-423
    • (2007) Comprehensive medicinal chemistry II , vol.5 , pp. 399-423
    • Avdeef, A.1    Voloboy, D.2    Foreman, A.3
  • 20
    • 0018702799 scopus 로고
    • Solubility determination of barely aqueous-soluble organic solids
    • Higuchi T., Shih F.-M., Kimura T., and Rytting J.H. Solubility determination of barely aqueous-soluble organic solids. J. Pharm. Sci. 68 (1979) 1267-1272
    • (1979) J. Pharm. Sci. , vol.68 , pp. 1267-1272
    • Higuchi, T.1    Shih, F.-M.2    Kimura, T.3    Rytting, J.H.4
  • 21
    • 0029969048 scopus 로고    scopus 로고
    • Intrinsic solubility estimation and pH-solubility behavior of cosalane (NSC658586), an extremely hydrphobic diprotic acid
    • Venkatesh S., Li J., Xu Y., Vishnuvajjala R., and Anderson B.D. Intrinsic solubility estimation and pH-solubility behavior of cosalane (NSC658586), an extremely hydrphobic diprotic acid. Pharm. Res. 13 (1996) 1453-1459
    • (1996) Pharm. Res. , vol.13 , pp. 1453-1459
    • Venkatesh, S.1    Li, J.2    Xu, Y.3    Vishnuvajjala, R.4    Anderson, B.D.5
  • 22
    • 0027198995 scopus 로고
    • Solubility of ionization behavior of the antifungal α-(2,4-difluorophenyl)-α -[(1-(2-(2-pyridyl)phenylethenyl)]-1H-1,2,4-triazole-1-ethanol bismesylate (XD405)
    • Maurin M.B., Vickery R.D., Gerard C.A., and Hussain M. Solubility of ionization behavior of the antifungal α-(2,4-difluorophenyl)-α -[(1-(2-(2-pyridyl)phenylethenyl)]-1H-1,2,4-triazole-1-ethanol bismesylate (XD405). Int. J. Pharm. 94 (1993) 11-14
    • (1993) Int. J. Pharm. , vol.94 , pp. 11-14
    • Maurin, M.B.1    Vickery, R.D.2    Gerard, C.A.3    Hussain, M.4
  • 23
    • 0017804349 scopus 로고
    • Aggregation of antidepressant drugs in aqueous solution
    • Attwood D., and Gibson J. Aggregation of antidepressant drugs in aqueous solution. J.Pharm. Pharmacol. 30 (1978) 176-180
    • (1978) J.Pharm. Pharmacol. , vol.30 , pp. 176-180
    • Attwood, D.1    Gibson, J.2
  • 24
    • 0018412446 scopus 로고
    • Solubility of doxycycline in aqueous solution
    • Bogardus J.B., and Blackwood Jr. R.K. Solubility of doxycycline in aqueous solution. J.Pharm. Sci. 68 (1979) 188-194
    • (1979) J.Pharm. Sci. , vol.68 , pp. 188-194
    • Bogardus, J.B.1    Blackwood Jr., R.K.2
  • 25
    • 0030591411 scopus 로고    scopus 로고
    • Determination of solution aggregation using solubility, conductivity, calorimetry, and pH measurement
    • Streng W.H., Yu D.H.-S., and Zhu C. Determination of solution aggregation using solubility, conductivity, calorimetry, and pH measurement. Int. J. Pharm. 135 (1996) 43-52
    • (1996) Int. J. Pharm. , vol.135 , pp. 43-52
    • Streng, W.H.1    Yu, D.H.-S.2    Zhu, C.3
  • 26
    • 0343408252 scopus 로고    scopus 로고
    • Investigation of drug self-association in aqueous solution using calorimetry, conductivity, and osmometry
    • Zhu C., and Streng W.H. Investigation of drug self-association in aqueous solution using calorimetry, conductivity, and osmometry. Int. J. Pharm. 130 (1996) 159-168
    • (1996) Int. J. Pharm. , vol.130 , pp. 159-168
    • Zhu, C.1    Streng, W.H.2
  • 27
    • 0027426899 scopus 로고
    • Salt and mesophase formation in aqueous suspensions of lauric acid
    • Smith S.W., and Anderson B.D. Salt and mesophase formation in aqueous suspensions of lauric acid. Pharm. Res. 10 (1993) 1533-1543
    • (1993) Pharm. Res. , vol.10 , pp. 1533-1543
    • Smith, S.W.1    Anderson, B.D.2
  • 28
    • 0029557485 scopus 로고
    • Solubility and solubilization properties of non-steroidal antiinflammatory drugs
    • Fini A., Fazio G., and Feroci G. Solubility and solubilization properties of non-steroidal antiinflammatory drugs. Int. J. Pharm. 126 (1995) 95-102
    • (1995) Int. J. Pharm. , vol.126 , pp. 95-102
    • Fini, A.1    Fazio, G.2    Feroci, G.3
  • 29
    • 33847095950 scopus 로고    scopus 로고
    • Solubility-excipient classification gradient maps
    • Avdeef A., Bendels S., Tsinman O., and Kansy M. Solubility-excipient classification gradient maps. Pharm. Res. 24 (2007) 530-545
    • (2007) Pharm. Res. , vol.24 , pp. 530-545
    • Avdeef, A.1    Bendels, S.2    Tsinman, O.3    Kansy, M.4
  • 30
    • 0015868160 scopus 로고
    • 2∝ (tromethamine salt): solubility behaviour, surface properties, and ionization constants
    • 2∝ (tromethamine salt): solubility behaviour, surface properties, and ionization constants. J. Pharm. Sci. 62 (1973) 1680-1685
    • (1973) J. Pharm. Sci. , vol.62 , pp. 1680-1685
    • Roseman, T.J.1    Yalkowsky, S.H.2
  • 31
    • 0033997669 scopus 로고    scopus 로고
    • Dissolution of ionizable water-insoluble drugs: the combined effect of pH and surfactant
    • Jinno J., Oh D.-M., Crison J.R., and Amidon G.L. Dissolution of ionizable water-insoluble drugs: the combined effect of pH and surfactant. J. Pharm. Sci. 89 (2000) 268-274
    • (2000) J. Pharm. Sci. , vol.89 , pp. 268-274
    • Jinno, J.1    Oh, D.-M.2    Crison, J.R.3    Amidon, G.L.4
  • 32
    • 34548025369 scopus 로고    scopus 로고
    • A. Avdeef, High-throughput measurements of solubility profiles, in: B. Testa, H. van de Waterbeemd, G. Folkers, R. Guy (Eds.), Pharmacokinetic Optimization in Drug Research, Verlag Helvetica Chimica Acta, Zürich and Wiley - VCH, Weinheim, 2001, pp. 305-326.
  • 33
    • 0036809320 scopus 로고    scopus 로고
    • Physicochemical profiling in drug research: a brief state-of-the-art of experimental techniques
    • Avdeef A., and Testa B. Physicochemical profiling in drug research: a brief state-of-the-art of experimental techniques. Cell. Mol. Life Sci. 59 (2003) 1681-1689
    • (2003) Cell. Mol. Life Sci. , vol.59 , pp. 1681-1689
    • Avdeef, A.1    Testa, B.2
  • 35
    • 0016709319 scopus 로고
    • Micelle formation and its relationship to solubility behavior of 2-butyl-3-benzofuranyl-4-(2-(diethylamino) ethoxy)-3,5-diiodophenylketone hydrochloride
    • Ravin L.J., Shami E.G., and Rattie E.S. Micelle formation and its relationship to solubility behavior of 2-butyl-3-benzofuranyl-4-(2-(diethylamino) ethoxy)-3,5-diiodophenylketone hydrochloride. J. Pharm. Sci. 64 (1975) 1830-1833
    • (1975) J. Pharm. Sci. , vol.64 , pp. 1830-1833
    • Ravin, L.J.1    Shami, E.G.2    Rattie, E.S.3
  • 37
    • 0027177561 scopus 로고
    • Solubilization of thiazolobenzimidazole using a combination of pH adjustment and complexation with 2-hydroxy-β-cyclodextrin
    • Tinwalla A.Y., Hoesterey B.L., Xiang T.-X., Lim K., and Anderson B.D. Solubilization of thiazolobenzimidazole using a combination of pH adjustment and complexation with 2-hydroxy-β-cyclodextrin. Pharm. Res. 10 (1993) 1136-1143
    • (1993) Pharm. Res. , vol.10 , pp. 1136-1143
    • Tinwalla, A.Y.1    Hoesterey, B.L.2    Xiang, T.-X.3    Lim, K.4    Anderson, B.D.5
  • 38
    • 0028107024 scopus 로고
    • Solubilization of a tripeptide HIV protease inhibitor using a combination of ionization and complexation with chemically modified cyclodextrins
    • Johnson M.D., Hoesterey B.L., and Anderson B.D. Solubilization of a tripeptide HIV protease inhibitor using a combination of ionization and complexation with chemically modified cyclodextrins. J. Pharm. Sci. 83 (1994) 1142-1146
    • (1994) J. Pharm. Sci. , vol.83 , pp. 1142-1146
    • Johnson, M.D.1    Hoesterey, B.L.2    Anderson, B.D.3
  • 39
    • 0030053698 scopus 로고    scopus 로고
    • The interaction of charged and uncharged drugs with neutral (HP-β-CD) and anionically charged (SBE7-β-CD) β-cyclodextrins
    • Okimoto K., Rajewski R.A., Uekama K., Jona J.A., and Stella V.J. The interaction of charged and uncharged drugs with neutral (HP-β-CD) and anionically charged (SBE7-β-CD) β-cyclodextrins. Pharm. Res. 13 (1996) 256-264
    • (1996) Pharm. Res. , vol.13 , pp. 256-264
    • Okimoto, K.1    Rajewski, R.A.2    Uekama, K.3    Jona, J.A.4    Stella, V.J.5
  • 41
    • 33750151347 scopus 로고    scopus 로고
    • Solubilization and dissolution of insoluble weak acid, ketoprofen: effect of pH combined with surfactant
    • Sheng J.J., Kasim N.A., Chandrasekharan R., and Amidon G.L. Solubilization and dissolution of insoluble weak acid, ketoprofen: effect of pH combined with surfactant. Eur. J. Pharm. Sci. 29 (2006) 306-314
    • (2006) Eur. J. Pharm. Sci. , vol.29 , pp. 306-314
    • Sheng, J.J.1    Kasim, N.A.2    Chandrasekharan, R.3    Amidon, G.L.4
  • 42
    • 0018726933 scopus 로고
    • Interaction of drugs with bile components. I. Effects of bile salts on the dissolution of indomethacin and phenylbutazone
    • Miyazaki S., Inouie H., Yamahira T., and Nadai T. Interaction of drugs with bile components. I. Effects of bile salts on the dissolution of indomethacin and phenylbutazone. Chem. Pharm. Bull. 27 (1979) 2468-2472
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 2468-2472
    • Miyazaki, S.1    Inouie, H.2    Yamahira, T.3    Nadai, T.4
  • 43
    • 0025930844 scopus 로고
    • Solubilization and wetting effects of bile salts in the dissolution of steroids
    • Bakatselou V., Oppenheim R.C., and Dressman J.B. Solubilization and wetting effects of bile salts in the dissolution of steroids. Pharm. Res. 8 (1991) 1461-1469
    • (1991) Pharm. Res. , vol.8 , pp. 1461-1469
    • Bakatselou, V.1    Oppenheim, R.C.2    Dressman, J.B.3
  • 44
    • 0030003789 scopus 로고    scopus 로고
    • Estimation of the increase in solubility of drugs as a function of bile salt concentration
    • Mithani S.D., Bakatselou V., TenHoor C.N., and Dressman J.B. Estimation of the increase in solubility of drugs as a function of bile salt concentration. Pharm. Res. 13 (1996) 163-167
    • (1996) Pharm. Res. , vol.13 , pp. 163-167
    • Mithani, S.D.1    Bakatselou, V.2    TenHoor, C.N.3    Dressman, J.B.4
  • 45
    • 0028080807 scopus 로고
    • The effects of bile salts and lipids on the physicochemical behavior of gemfibrozil
    • Luner P.E., Babu S.R., and Radebaugh G.W. The effects of bile salts and lipids on the physicochemical behavior of gemfibrozil. Pharm. Res. 11 (1994) 1755-1760
    • (1994) Pharm. Res. , vol.11 , pp. 1755-1760
    • Luner, P.E.1    Babu, S.R.2    Radebaugh, G.W.3
  • 46
    • 33747759752 scopus 로고    scopus 로고
    • Biorelevant dissolution media as a predictive tool for glyburide a class II drug
    • Wei H., and Löbenberg R. Biorelevant dissolution media as a predictive tool for glyburide a class II drug. Eur. J. Pharm. Sci. 29 (2006) 45-52
    • (2006) Eur. J. Pharm. Sci. , vol.29 , pp. 45-52
    • Wei, H.1    Löbenberg, R.2
  • 47
    • 0034006672 scopus 로고    scopus 로고
    • pH-metric solubility. 2. Correlation between the acid-base titration and the saturation shake-flask solubility-pH methods
    • Avdeef A., Berger C.M., and Brownell C. pH-metric solubility. 2. Correlation between the acid-base titration and the saturation shake-flask solubility-pH methods. Pharm. Res. 17 (2000) 85-89
    • (2000) Pharm. Res. , vol.17 , pp. 85-89
    • Avdeef, A.1    Berger, C.M.2    Brownell, C.3
  • 48
    • 0034773359 scopus 로고    scopus 로고
    • pH-metric solubility. 3. Dissolution titration template method for solubility determination
    • Avdeef A., and Berger C.M. pH-metric solubility. 3. Dissolution titration template method for solubility determination. Eur. J. Pharm. Sci. 14 (2001) 281-291
    • (2001) Eur. J. Pharm. Sci. , vol.14 , pp. 281-291
    • Avdeef, A.1    Berger, C.M.2
  • 49
    • 12244263506 scopus 로고    scopus 로고
    • Comparison of a miniaturized shake-flask solubility method with automated potentiometric acid/base titrations and calculated solubilities
    • Glomme A., März J., and Dressman J.B. Comparison of a miniaturized shake-flask solubility method with automated potentiometric acid/base titrations and calculated solubilities. J. Pharm. Sci. 94 (2005) 1-16
    • (2005) J. Pharm. Sci. , vol.94 , pp. 1-16
    • Glomme, A.1    März, J.2    Dressman, J.B.3
  • 51
    • 3242717497 scopus 로고    scopus 로고
    • Accuracy of calculated pH-dependent aqueous drug solubility
    • Bergström C.A.S., Luthman K., and Artursson P. Accuracy of calculated pH-dependent aqueous drug solubility. Eur. J. Pharm. Sci. 22 (2004) 387-398
    • (2004) Eur. J. Pharm. Sci. , vol.22 , pp. 387-398
    • Bergström, C.A.S.1    Luthman, K.2    Artursson, P.3
  • 52
    • 34247552300 scopus 로고    scopus 로고
    • Development of a partially automated solubility screening (PASS) assay for early drug development
    • Alsenz J., Meister E., and Haenel E. Development of a partially automated solubility screening (PASS) assay for early drug development. J. Pharm. Sci. 96 (2007) 1748-1762
    • (2007) J. Pharm. Sci. , vol.96 , pp. 1748-1762
    • Alsenz, J.1    Meister, E.2    Haenel, E.3
  • 53
    • 33750000906 scopus 로고    scopus 로고
    • High throughput solubility measurement with automated polarized light microscopy analysis
    • Sugano K., Kato T., Suzuki K., Keiko K., Sujaku T., and Mano T. High throughput solubility measurement with automated polarized light microscopy analysis. J. Pharm. Sci. 95 (2006) 2115-2122
    • (2006) J. Pharm. Sci. , vol.95 , pp. 2115-2122
    • Sugano, K.1    Kato, T.2    Suzuki, K.3    Keiko, K.4    Sujaku, T.5    Mano, T.6
  • 54
    • 0036828814 scopus 로고    scopus 로고
    • Evaluation of a method for high throughput solubility determination using a multi-wavelength UV plate reader
    • Chen T.-M., Shen H., and Zhu C. Evaluation of a method for high throughput solubility determination using a multi-wavelength UV plate reader. Comb. Chem. High Throughput Screen. 5 (2002) 575-581
    • (2002) Comb. Chem. High Throughput Screen. , vol.5 , pp. 575-581
    • Chen, T.-M.1    Shen, H.2    Zhu, C.3
  • 56
    • 0035069173 scopus 로고    scopus 로고
    • Comparison of chromatographic and spectroscopic methods used to rank compounds for aqueous solubility
    • Pan L., Ho Q., Tsutsui K., and Takahashi L. Comparison of chromatographic and spectroscopic methods used to rank compounds for aqueous solubility. J. Pharm. Sci. 90 (2001) 521-529
    • (2001) J. Pharm. Sci. , vol.90 , pp. 521-529
    • Pan, L.1    Ho, Q.2    Tsutsui, K.3    Takahashi, L.4
  • 58
    • 0035150465 scopus 로고    scopus 로고
    • High throughput physicochemical profiling for drug discovery
    • Kerns E.H. High throughput physicochemical profiling for drug discovery. J. Pharm. Sci. 90 (2001) 1838-1858
    • (2001) J. Pharm. Sci. , vol.90 , pp. 1838-1858
    • Kerns, E.H.1
  • 59
    • 0021702316 scopus 로고
    • General treatment of pH-solubility profiles of weak acids and bases and the effect of different acids on the solubility of a weak base
    • Streng W.H., His S.K., Helms P.E., and Tan H.G.H. General treatment of pH-solubility profiles of weak acids and bases and the effect of different acids on the solubility of a weak base. J. Pharm. Sci. 73 (1984) 1679-1684
    • (1984) J. Pharm. Sci. , vol.73 , pp. 1679-1684
    • Streng, W.H.1    His, S.K.2    Helms, P.E.3    Tan, H.G.H.4
  • 61
    • 0036282656 scopus 로고    scopus 로고
    • Solubility of E2050 at various pH: a case in which the apparent solubility is affected by the amount of excess solid
    • Wang Z., Burrell L.S., and Lambert W.J. Solubility of E2050 at various pH: a case in which the apparent solubility is affected by the amount of excess solid. J. Pharm. Sci. 91 (2002) 1445-1455
    • (2002) J. Pharm. Sci. , vol.91 , pp. 1445-1455
    • Wang, Z.1    Burrell, L.S.2    Lambert, W.J.3
  • 62
    • 24044470016 scopus 로고    scopus 로고
    • Impact of the amount of excess solids on apparent solubility
    • Kawakami K., Miyoshi K., and Ida Y. Impact of the amount of excess solids on apparent solubility. Pharm. Res. 22 (2005) 1537-1543
    • (2005) Pharm. Res. , vol.22 , pp. 1537-1543
    • Kawakami, K.1    Miyoshi, K.2    Ida, Y.3
  • 64
    • 0000434173 scopus 로고
    • Accurate measurements of the concentration of hydrogen ions with a glass electrode: calibrations using the prideaux and other universal buffer solutions and a computer-controlled automatic titrator
    • Avdeef A., and Bucher J.J. Accurate measurements of the concentration of hydrogen ions with a glass electrode: calibrations using the prideaux and other universal buffer solutions and a computer-controlled automatic titrator. Anal. Chem. 50 (1978) 2137-2142
    • (1978) Anal. Chem. , vol.50 , pp. 2137-2142
    • Avdeef, A.1    Bucher, J.J.2
  • 65
    • 0027245634 scopus 로고
    • pH-metric logP. 2. Refinement of partition coefficients and ionization constants of multiprotic substances
    • Avdeef A. pH-metric logP. 2. Refinement of partition coefficients and ionization constants of multiprotic substances. J. Pharm. Sci. 82 (1993) 183-190
    • (1993) J. Pharm. Sci. , vol.82 , pp. 183-190
    • Avdeef, A.1
  • 67
    • 0020616875 scopus 로고
    • Dissociation constants, solubilities and dissociation rates of some selected nonsteroidal antiinflammatories
    • Herzfeldt C.D., and Kummel R. Dissociation constants, solubilities and dissociation rates of some selected nonsteroidal antiinflammatories. Drug Dev. Ind. Pharm. 9 (1983) 767-793
    • (1983) Drug Dev. Ind. Pharm. , vol.9 , pp. 767-793
    • Herzfeldt, C.D.1    Kummel, R.2
  • 68
    • 0021331173 scopus 로고
    • pH-solubility relationship and partition coefficients for some anti-inflammatory arylaliphatic acids
    • Chiarini A., Tartarini A., and Fini A. pH-solubility relationship and partition coefficients for some anti-inflammatory arylaliphatic acids. Arch. Pharm. 317 (1984) 268-273
    • (1984) Arch. Pharm. , vol.317 , pp. 268-273
    • Chiarini, A.1    Tartarini, A.2    Fini, A.3
  • 69
    • 0018145767 scopus 로고
    • pH-solubility profiles of organic carboxylic acids and their salts
    • Chowhan Z.T. pH-solubility profiles of organic carboxylic acids and their salts. J. Pharm. Sci. 67 (1978) 1257-1260
    • (1978) J. Pharm. Sci. , vol.67 , pp. 1257-1260
    • Chowhan, Z.T.1
  • 70
    • 0031791409 scopus 로고    scopus 로고
    • Effects of surface active characteristics and solid state forms on the pH solubility profiles of drug-salt systems
    • Ledwidge M.T., and Corrigan O.I. Effects of surface active characteristics and solid state forms on the pH solubility profiles of drug-salt systems. Int. J. Pharm. 174 (1998) 187-200
    • (1998) Int. J. Pharm. , vol.174 , pp. 187-200
    • Ledwidge, M.T.1    Corrigan, O.I.2
  • 71
    • 0017714374 scopus 로고
    • Solubility and ionization characteristics of phenytoin
    • Schwartz P.A., Rhodes C.T., and Cooper Jr. J.W. Solubility and ionization characteristics of phenytoin. J. Pharm. Sci. 66 (1977) 994-997
    • (1977) J. Pharm. Sci. , vol.66 , pp. 994-997
    • Schwartz, P.A.1    Rhodes, C.T.2    Cooper Jr., J.W.3
  • 72
    • 0018968221 scopus 로고
    • Pro-drugs as drug delivery systems, VIII Bioreversible derivatization of hydantoin by N-hydroxymethylation
    • Bundgaard H., and Johansen M. Pro-drugs as drug delivery systems, VIII Bioreversible derivatization of hydantoin by N-hydroxymethylation. Int. J. Pharm. 5 (1980) 67-77
    • (1980) Int. J. Pharm. , vol.5 , pp. 67-77
    • Bundgaard, H.1    Johansen, M.2
  • 73
    • 0021129880 scopus 로고
    • pH-solubility profile of papaverine hydrochloride and its relationship to the dissolution rate of sustained-release pellets
    • Serajuddin A.T.M., and Rosoff M. pH-solubility profile of papaverine hydrochloride and its relationship to the dissolution rate of sustained-release pellets. J. Pharm. Sci. 73 (1984) 1203-1208
    • (1984) J. Pharm. Sci. , vol.73 , pp. 1203-1208
    • Serajuddin, A.T.M.1    Rosoff, M.2
  • 74
    • 0018391430 scopus 로고
    • Solubility characteristics of weak bases and their hydrochloride salts in hydrochloric acid solutions
    • Miyazaki S., Inouie H., Nadai T., Arita T., and Nakano M. Solubility characteristics of weak bases and their hydrochloride salts in hydrochloric acid solutions. Chem. Pharm. Bull. 27 (1979) 1441-1447
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 1441-1447
    • Miyazaki, S.1    Inouie, H.2    Nadai, T.3    Arita, T.4    Nakano, M.5
  • 75
    • 0031786697 scopus 로고    scopus 로고
    • Co-administration of a water-soluble polymer increases the usefulness of cyclodextrins in solid oral dosage forms
    • Savolainen J., Järvinen K., Taipale H., Jarho P., Loftsson T., and Järvinen T. Co-administration of a water-soluble polymer increases the usefulness of cyclodextrins in solid oral dosage forms. Pharm. Res. 15 (1998) 1696-1701
    • (1998) Pharm. Res. , vol.15 , pp. 1696-1701
    • Savolainen, J.1    Järvinen, K.2    Taipale, H.3    Jarho, P.4    Loftsson, T.5    Järvinen, T.6
  • 76
    • 0031742889 scopus 로고    scopus 로고
    • Combined effect of complexation and pH on solubilization
    • Li P., Esmail S., and Yalkowsky S.H. Combined effect of complexation and pH on solubilization. J. Pharm. Sci. 87 (1998) 1535-1537
    • (1998) J. Pharm. Sci. , vol.87 , pp. 1535-1537
    • Li, P.1    Esmail, S.2    Yalkowsky, S.H.3
  • 77
    • 0242691754 scopus 로고    scopus 로고
    • Formation of natamycin-cyclodextrin inclusion complexes and their characterization
    • Koontz J.L., and Marcy J.E. Formation of natamycin-cyclodextrin inclusion complexes and their characterization. J. Agric. Food Chem. 51 (2003) 7106-7110
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 7106-7110
    • Koontz, J.L.1    Marcy, J.E.2
  • 78
    • 13544258798 scopus 로고    scopus 로고
    • Preformulation study of the inclusion complex warfarin-β-cyclodextrin
    • Zingone G., and Rubessa F. Preformulation study of the inclusion complex warfarin-β-cyclodextrin. Int. J. Pharm. 291 (2005) 3-10
    • (2005) Int. J. Pharm. , vol.291 , pp. 3-10
    • Zingone, G.1    Rubessa, F.2
  • 79
    • 2942714975 scopus 로고    scopus 로고
    • Evidence for the 2:1 molecular recognition and inclusion behavior between β- and γ-cyclodextrins and cinchonine
    • Wen X., Liu Z., Zhu T., Zhu M., Jiang K., and Huang Q. Evidence for the 2:1 molecular recognition and inclusion behavior between β- and γ-cyclodextrins and cinchonine. Bioorg. Chem. 32 (2004) 223-233
    • (2004) Bioorg. Chem. , vol.32 , pp. 223-233
    • Wen, X.1    Liu, Z.2    Zhu, T.3    Zhu, M.4    Jiang, K.5    Huang, Q.6
  • 81
    • 33846047876 scopus 로고    scopus 로고
    • Interaction of omeprazole with a methylated derivative of β-cyclodextrin: phase solubility, NMR spectroscopy and molecular simulation
    • Figueiras A., Sarraguaça J.M.G., Carhalho R.A., Pais A.A.C.C., and Veiga F.J.B. Interaction of omeprazole with a methylated derivative of β-cyclodextrin: phase solubility, NMR spectroscopy and molecular simulation. Pharm. Sci. 24 (2006) 377-389
    • (2006) Pharm. Sci. , vol.24 , pp. 377-389
    • Figueiras, A.1    Sarraguaça, J.M.G.2    Carhalho, R.A.3    Pais, A.A.C.C.4    Veiga, F.J.B.5
  • 82
    • 33846521876 scopus 로고    scopus 로고
    • Cyclodextrin/imatinib complexation: binding mode and charge dependent stabilities
    • Béni S., Szakács Z., Csernák O., Barcza L., and Noszál B. Cyclodextrin/imatinib complexation: binding mode and charge dependent stabilities. Eur. J. Pharm. Sci. 30 (2007) 167-174
    • (2007) Eur. J. Pharm. Sci. , vol.30 , pp. 167-174
    • Béni, S.1    Szakács, Z.2    Csernák, O.3    Barcza, L.4    Noszál, B.5
  • 83
    • 0019513805 scopus 로고
    • Precaution on use of hydrochloride salts in pharmaceutical formulation
    • Miyazaki S., Oshiba M., and Nadai T. Precaution on use of hydrochloride salts in pharmaceutical formulation. J. Pharm. Sci. 70 (1981) 594-596
    • (1981) J. Pharm. Sci. , vol.70 , pp. 594-596
    • Miyazaki, S.1    Oshiba, M.2    Nadai, T.3
  • 84
    • 0021876419 scopus 로고
    • Predictive relationships in the water solubility of salts of a nonsteroidal anti-inflammatory drug
    • Anderson B.D., and Conradi R.A. Predictive relationships in the water solubility of salts of a nonsteroidal anti-inflammatory drug. J. Pharm. Sci. 74 (1985) 815-820
    • (1985) J. Pharm. Sci. , vol.74 , pp. 815-820
    • Anderson, B.D.1    Conradi, R.A.2
  • 85
    • 0025153729 scopus 로고
    • Aqueous solubility properties of a dibasic peptide-like compound
    • Garren K.W., and Pyter R.A. Aqueous solubility properties of a dibasic peptide-like compound. Int. J. Pharm. 63 (1990) 167-172
    • (1990) Int. J. Pharm. , vol.63 , pp. 167-172
    • Garren, K.W.1    Pyter, R.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.