메뉴 건너뛰기




Volumn 453, Issue 1, 2013, Pages 88-100

Use of pharmaceutical salts and cocrystals to address the issue of poor solubility

Author keywords

Cocrystals; Dissolution rate; Intrinsic solubility; Low soluble drugs; Salts

Indexed keywords

COUNTERION; SODIUM CHLORIDE;

EID: 84879714763     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2012.11.028     Document Type: Review
Times cited : (312)

References (104)
  • 1
    • 34250863849 scopus 로고    scopus 로고
    • Cocrystal or salt: Does it really matter?
    • DOI 10.1021/mp060126o
    • Aakeröy, C.B., Fasulo, M.B., Desper, J., 2007. Cocrystal or salt: Does it really matter? Mol. Pharm. 4, 317-322. (Pubitemid 46983948)
    • (2007) Molecular Pharmaceutics , vol.4 , Issue.3 , pp. 317-322
    • Aakeroy, C.B.1    Fasulo, M.E.2    Desper, J.3
  • 2
    • 0017158036 scopus 로고
    • Enhancement of solubility of drug salts by hydrophilic counterions: Properties of organic salts of an antimalarial drug
    • Agharkar, S., Lindenbaum, S., Higuchi, T., 1976. Enhancement of solubility of drug salts by hydrophilic counterions: properties of organic salts of an antimalarial drug. J. Pharm. Sci. 65, 747-749.
    • (1976) J. Pharm. Sci. , vol.65 , pp. 747-749
    • Agharkar, S.1    Lindenbaum, S.2    Higuchi, T.3
  • 4
    • 85030489181 scopus 로고    scopus 로고
    • Overcoming formulation problems and some case studies
    • Akers, M.J. (Ed.), Informa Healthcare, London
    • Akers, M.J., 2008. Overcoming formulation problems and some case studies. In: Akers, M.J. (Ed.), Sterile Drug Products. Formulation, Packaging, Manufacturing and Quality. Informa Healthcare, London, pp. 169-179.
    • (2008) Sterile Drug Products. Formulation, Packaging, Manufacturing and Quality , pp. 169-179
    • Akers, M.J.1
  • 5
    • 0001056344 scopus 로고    scopus 로고
    • Preparation of water soluble compounds through salt formation
    • Wermuth, C.G. (Ed.), Academic Press, London
    • Anderson, B.D., Flora, K.P., 1996. Preparation of water soluble compounds through salt formation. In: Wermuth, C.G. (Ed.), The Practices of Medicinal Chemistry. Academic Press, London, pp. 739-754.
    • (1996) The Practices of Medicinal Chemistry , pp. 739-754
    • Anderson, B.D.1    Flora, K.P.2
  • 6
    • 0026457856 scopus 로고
    • Sustained propranolol delivert and increased oral bioavailability in dogs given a propranolol laurate salt
    • Aungst, B.J., Hussain, M.A., 1992. Sustained propranolol delivert and increased oral bioavailability in dogs given a propranolol laurate salt. Pharm. Res. 9, 1107-1109.
    • (1992) Pharm. Res. , vol.9 , pp. 1107-1109
    • Aungst, B.J.1    Hussain, M.A.2
  • 8
    • 27744484364 scopus 로고    scopus 로고
    • Saccharin salts of active pharmaceutical ingredients, their crystal structures, and increased water solubilities
    • DOI 10.1021/cg050125l
    • Banerjeree, R., Bhatt, P.M., Ravindra, N.V., Desiraju, G.R., 2005. Saccharin salts of active pharmaceutical ingredients, their crystal structures and increased water solubilities. Cryst. Growth Des. 5, 2299-2309. (Pubitemid 41619324)
    • (2005) Crystal Growth and Design , vol.5 , Issue.6 , pp. 2299-2309
    • Banerjee, R.1    Bhatt, P.M.2    Ravindra, N.V.3    Desiraju, G.R.4
  • 9
    • 0034345216 scopus 로고    scopus 로고
    • Salt selection and optimisation for pharmaceutical new chemical entities
    • Bastin, R.J., Bowker, M.J., Slater, B.J., 2000. Salt selection and optimisation for pharmaceutical new chemical entities. Org. Proc. Res. Dev. 4, 427-435.
    • (2000) Org. Proc. Res. Dev. , vol.4 , pp. 427-435
    • Bastin, R.J.1    Bowker, M.J.2    Slater, B.J.3
  • 14
    • 0015591509 scopus 로고
    • Effect of complexation with phenobarbital on the biologic availability of theophyline from three tablet formulastions
    • Bettis, J.W., Lach, J.L., Hood, J., 1973. Effect of complexation with phenobarbital on the biologic availability of theophyline from three tablet formulastions. Am. J. Hosp. Pharm. 30, 240-243.
    • (1973) Am. J. Hosp. Pharm. , vol.30 , pp. 240-243
    • Bettis, J.W.1    Lach, J.L.2    Hood, J.3
  • 16
    • 0029070763 scopus 로고
    • Pharmaceutical solids-a strategic approach to regulatory considerations
    • Byrn, S., Pfeiffer, R., Ganey, M., Hoiberg, C., Poochikian, G., 1995. Pharmaceutical solids-a strategic approach to regulatory considerations. Pharm. Res. 12, 945-954.
    • (1995) Pharm. Res. , vol.12 , pp. 945-954
    • Byrn, S.1    Pfeiffer, R.2    Ganey, M.3    Hoiberg, C.4    Poochikian, G.5
  • 17
    • 0013218013 scopus 로고    scopus 로고
    • The absolute configuration of sertraline (Zoloft) hydrochloride
    • Caruso, F., Besmer, A., Rossi, M., 1999. The absolute configuration of sertraline (Zoloft) hydrochloride. Acta Cryst. C 55, 1712.
    • (1999) Acta Cryst. C , vol.55 , pp. 1712
    • Caruso, F.1    Besmer, A.2    Rossi, M.3
  • 19
    • 0025239647 scopus 로고
    • Reduction of dimethyl sulfoxide by dihydrohalide salts of pharmaceuticals
    • DOI 10.1016/0378-5173(90)90111-G
    • Chen, T.K., Thornton, D., Ho, M.Y.K., 1990. Reduction of dimethylsulfoxide by dihydrohalide salts of pharmaceuticals. Int. J. Pharm. 59, 211-216. (Pubitemid 20146152)
    • (1990) International Journal of Pharmaceutics , vol.59 , Issue.3 , pp. 211-216
    • Chen, T.K.1    Thornton, D.2    Ho, M.Y.K.3
  • 21
    • 58149242453 scopus 로고    scopus 로고
    • Aqueous versus non-aqueous salt delivery strategies to enhance oral bioavailability of a mitogen-activated protein kinase-activated protein kinase (MK-2) inhibitor in rats
    • Chiang, P.-C., South, S.A., Daniels, J.S., Anderson, D.R., Wene, S.P., Albin, L.A., Mourey, R.J., Selbo, J.G., 2009. Aqueous versus non-aqueous salt delivery strategies to enhance oral bioavailability of a mitogen-activated protein kinase-activated protein kinase (MK-2) inhibitor in rats. J. Pharm. Sci. 98, 248-256.
    • (2009) J. Pharm. Sci. , vol.98 , pp. 248-256
    • Chiang, P.-C.1    South, S.A.2    Daniels, J.S.3    Anderson, D.R.4    Wene, S.P.5    Albin, L.A.6    Mourey, R.J.7    Selbo, J.G.8
  • 22
    • 6044264984 scopus 로고    scopus 로고
    • Crystal engineering approach to forming cocrystals of amine hydrochlorides with organic acids. Molecular complexes of fluoxetine hydrochloride with benzoic, succinic, and fumaric acids
    • Childs, S.L., Chyall, L.J., Dunlap, J.T., Smolenskaya, V.N., Stahly, B.C., Stahly, P.J., 2004 Crystal engineering approach to forming cocrystals of amine hydrochlorides with organic acids. Molecular complexes of fluoxetine hydrochloride with benzoic, succinic, and fumaric acids. J. Am. Chem. Soc. 126, 13335-13342.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13335-13342
    • Childs, S.L.1    Chyall, L.J.2    Dunlap, J.T.3    Smolenskaya, V.N.4    Stahly, B.C.5    Stahly, P.J.6
  • 23
    • 34547486346 scopus 로고    scopus 로고
    • Cocrystals of piroxicam with carboxylic acids
    • Childs, S.L., Hardcastle, K.I., 2007. Cocrystals of piroxicam with carboxylic acids. Cryst. Growth Des. 7, 1291-1304.
    • (2007) Cryst. Growth Des. , vol.7 , pp. 1291-1304
    • Childs, S.L.1    Hardcastle, K.I.2
  • 24
    • 34250791543 scopus 로고    scopus 로고
    • The salt-cocrystal continuum: The influence of crystal structure on ionization state
    • DOI 10.1021/mp0601345
    • Childs, S.L., Stahly, G.P., Park, A., 2007. The salt-cocrystal continuum: The influence of crystal structure on ionization state. Mol. Pharm. 4, 323-338. (Pubitemid 46983949)
    • (2007) Molecular Pharmaceutics , vol.4 , Issue.3 , pp. 323-338
    • Childs, S.L.1    Stahly, G.P.2    Park, A.3
  • 25
    • 65249151820 scopus 로고    scopus 로고
    • Analysis of 50 crystal structures containing carbamezapine using the Materials module of Mercury CSD
    • Childs, S.L., Wood, P.A., Rodriguez-Hornedo, N., Reddy, L.S., Hardcastle, K.I., 2009. Analysis of 50 crystal structures containing carbamezapine using the Materials module of Mercury CSD. Crsyt. Growth Des. 9, 1869-1888.
    • (2009) Crsyt. Growth Des. , vol.9 , pp. 1869-1888
    • Childs, S.L.1    Wood, P.A.2    Rodriguez-Hornedo, N.3    Reddy, L.S.4    Hardcastle, K.I.5
  • 26
    • 82455188322 scopus 로고    scopus 로고
    • Impact of the counterion on the solubility and physicochemical properties of salts of carboxylic acid salts
    • David, S.E., Timmins, P., Conway, B.R., 2012. Impact of the counterion on the solubility and physicochemical properties of salts of carboxylic acid salts. Drug Dev. Ind. Pharm. 38, 93-103.
    • (2012) Drug Dev. Ind. Pharm. , vol.38 , pp. 93-103
    • David, S.E.1    Timmins, P.2    Conway, B.R.3
  • 27
    • 0347471246 scopus 로고    scopus 로고
    • High-throughput screening techniques for pre-formulation: Salt-selection and polymorph studies, scientific updates
    • Desrosiers, P., 2001. High-throughput screening techniques for pre-formulation: Salt-selection and polymorph studies, scientific updates. International Symposium on Polymorphism and Crystallization.
    • (2001) International Symposium on Polymorphism and Crystallization
    • Desrosiers, P.1
  • 29
    • 0033805179 scopus 로고    scopus 로고
    • In vitro-in vivo correlation for lipophilic poorly water soluble drugs
    • Dressman, J.B., Repas, C., 2000. In vitro-in vivo correlation for lipophilic poorly water soluble drugs. Eur. J. Pharm. Sci. 11, S73-S80.
    • (2000) Eur. J. Pharm. Sci. , vol.11
    • Dressman, J.B.1    Repas, C.2
  • 32
    • 84860456003 scopus 로고    scopus 로고
    • FDA, US Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER)
    • FDA, 2011. US Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER). Guidance for Industry: Regulatory Classification of Pharmaceutical Cocrystals.
    • (2011) Guidance for Industry: Regulatory Classification of Pharmaceutical Cocrystals
  • 33
    • 61649108172 scopus 로고    scopus 로고
    • Effect of the counterion on the solubility on isostructural pharmaceutical lamotrigine salts
    • Galcera, J., Mollins, E., 2009. Effect of the counterion on the solubility on isostructural pharmaceutical lamotrigine salts. Cryst. Growth Des. 9, 327-334.
    • (2009) Cryst. Growth Des. , vol.9 , pp. 327-334
    • Galcera, J.1    Mollins, E.2
  • 34
    • 8844219708 scopus 로고    scopus 로고
    • Drugs as materials: Valuing physical form in drug discovery
    • DOI 10.1038/nrd1550
    • Gardner, C.R., Walsh, C.T., Almarrson, O., 2004. Drugs as materials: Valuing physical form in drug discovery. Nat. Rev. Drug Disc. 3, 926-934. (Pubitemid 39529930)
    • (2004) Nature Reviews Drug Discovery , vol.3 , Issue.11 , pp. 926-934
    • Gardner, C.R.1    Walsh, C.T.2    Almarsson, O.3
  • 35
    • 66249101601 scopus 로고    scopus 로고
    • Solubility advantage of pharmaceutical cocrystals
    • Good, D.J., Rodríguez-Hornedo, N., 2009. Solubility advantage of pharmaceutical cocrystals. Cryst. Growth Des. 9, 2252-2264.
    • (2009) Cryst. Growth Des. , vol.9 , pp. 2252-2264
    • Good, D.J.1    Rodríguez-Hornedo, N.2
  • 36
    • 0023032232 scopus 로고
    • Salt selection for basic drugs
    • DOI 10.1016/0378-5173(86)90055-4
    • Gould, P.L., 1986. Salt selection for basic drugs. Int. J. Pharm. 33, 201-217. (Pubitemid 17197805)
    • (1986) International Journal of Pharmaceutics , vol.33 , Issue.1-3 , pp. 201-217
    • Gould, P.L.1
  • 38
    • 0023253722 scopus 로고
    • Preformulation salt selection. Physical property comparisons of the tris(hydroxymethyl)aminomethane (THAM) salts of four analgesic/antiinflammatory agents with the sodium salts and the free acids
    • Gu, L., Strickley, R.G., 1987. Preformulation salt selection. Physical property comparisions of the tris(hydroxymethyl)aminomethane (THAM) salts of 4 analgesic anti-inflammatory agents with sodium salts and the free acids. Pharm. Res., 4, 255-257. (Pubitemid 17110403)
    • (1987) Pharmaceutical Research , vol.4 , Issue.3 , pp. 255-257
    • Gu, L.1    Strickley, R.G.2
  • 40
    • 0030638567 scopus 로고    scopus 로고
    • Characterization and significance of the amorphous state in pharmaceutical systems
    • Hancock, B.C., Zografi, G., 1997. Characterization and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci. 86, 1-12.
    • (1997) J. Pharm. Sci. , vol.86 , pp. 1-12
    • Hancock, B.C.1    Zografi, G.2
  • 41
    • 33846945738 scopus 로고    scopus 로고
    • Escitalopram oxalate: Co-existence of oxalate dianions and oxalic acid molecules in the same crystal
    • Harrison, W.T.A., Yathirajan, H.S., Bindya, S., Anilkumar, H.G., Devaraju, 2007. Escitalopram oxalate: co-existence of oxalate dianions and oxalic acid molecules in the same crystal. Acta Cryst. C 63, 129-131.
    • (2007) Acta Cryst. C , vol.63 , pp. 129-131
    • Harrison, W.T.A.1    Yathirajan, H.S.2    Bindya, S.3    Anilkumar, H.G.4    Devaraju5
  • 43
    • 84884141953 scopus 로고    scopus 로고
    • Good manufacturing practice guide for active pharmaceutical ingredients
    • ICH Q7A, 10 November 2000
    • ICH Q7A, 2000. Good manufacturing practice guide for active pharmaceutical ingredients, ICH Harmonized Tripartite Guidance, 10 November 2000.
    • (2000) ICH Harmonized Tripartite Guidance
  • 46
    • 79951895459 scopus 로고    scopus 로고
    • Salts of hydrates of imiquimod, an immune response modifier
    • Kumar, T.L., Vishweshar, P., Babu, J.M., Vyas, K., 2009. Salts of hydrates of imiquimod, an immune response modifier. Cryst. Growth Des. 9, 4822-4829.
    • (2009) Cryst. Growth Des. , vol.9 , pp. 4822-4829
    • Kumar, T.L.1    Vishweshar, P.2    Babu, J.M.3    Vyas, K.4
  • 49
    • 74849101611 scopus 로고    scopus 로고
    • Large scale aspects of salt formation: Processing of intermediates and final products
    • Stahl, P.H., Wermuth, G. (Eds.), Wiley-VCH, Weinheim
    • Lee, S., Hoff, C., 2002. Large scale aspects of salt formation: processing of intermediates and final products. In: Stahl, P.H., Wermuth, G. (Eds.), Handbook of Pharmaceutical Salts; Properties, Selection and Use. Wiley-VCH, Weinheim, pp. 191-220.
    • (2002) Handbook of Pharmaceutical Salts; Properties, Selection and Use , pp. 191-220
    • Lee, S.1    Hoff, C.2
  • 50
    • 0034601240 scopus 로고    scopus 로고
    • Improving drug solubility for oral delivery using solid dispersions
    • DOI 10.1016/S0939-6411(00)00076-X, PII S093964110000076X
    • Leuner, C., Dressman, J., 2000. Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 50, 47-60. (Pubitemid 30326688)
    • (2000) European Journal of Pharmaceutics and Biopharmaceutics , vol.50 , Issue.1 , pp. 47-60
    • Leuner, C.1    Dressman, J.2
  • 51
    • 23844475290 scopus 로고    scopus 로고
    • Effect of chloride ion on dissolution of different salt forms of haloperidol, a model basic drug
    • DOI 10.1002/jps.20440
    • Li, S., Doyle, P., Metz, S., Royce, A.E., Serajuddin, A.T.M., 2005. Effect of chloride ion on dissolution of different salt forms of haloperidol, a model basic drug. J. Pharm. Sci. 94, 2224-2231. (Pubitemid 41665282)
    • (2005) Journal of Pharmaceutical Sciences , vol.94 , Issue.10 , pp. 2224-2231
    • Li, S.1    Doyle, P.2    Metz, S.3    Royce, A.E.4    Serajuddin, A.T.M.5
  • 53
    • 0015402055 scopus 로고
    • Preformulation investigations I: Relation of salt forms and biological activity of an experimental antihypertensive
    • Lin, S-L., Lachman, L., Swartz, C.J., Huebner, C.F., 1972. Preformulation investigations I: Relation of salt forms and biological activity of an experimental antihypertensive. J. Pharm. Sci. 61, 1418-1422.
    • (1972) J. Pharm. Sci. , vol.61 , pp. 1418-1422
    • Lin, S.-L.1    Lachman, L.2    Swartz, C.J.3    Huebner, C.F.4
  • 54
    • 0030927353 scopus 로고    scopus 로고
    • Characterization of fluids from the stomach and proximal jejunum in men and women
    • DOI 10.1023/A:1012107801889
    • Lindahl, A., Ungell, A.L., Lennernas, H., 1997. Characterization of the fluids from the stomach and proximal jejunum in men and women. Pharm. Res. 14, 497-502. (Pubitemid 27205011)
    • (1997) Pharmaceutical Research , vol.14 , Issue.4 , pp. 497-502
    • Lindahl, A.1    Ungell, A.-L.2    Knutson, L.3    Lennernas, H.4
  • 55
    • 0034461768 scopus 로고    scopus 로고
    • Drug-like properties and the causes of poor solubility and poor permeability
    • DOI 10.1016/S1056-8719(00)00107-6, PII S1056871900001076
    • Lipinski, C.A., 2000. Drug-like properties and the causes of poor solubility and permeability. J. Pharmacol. Toxicol. Meth. 44, 235-249. (Pubitemid 32239479)
    • (2000) Journal of Pharmacological and Toxicological Methods , vol.44 , Issue.1 , pp. 235-249
    • Lipinski, C.A.1
  • 56
    • 30344440543 scopus 로고    scopus 로고
    • Solubility in water and DMSO: Issues and potential solutions
    • Borchardt, R.T., Kerns, E.H., Lipinski, C.A., Thakker, D.R., Wang, B. (Eds.), AAPS Press, Arlington, Virginia
    • Lipinski, C.A., 2004. Solubility in water and DMSO: Issues and potential solutions. In: Borchardt, R.T., Kerns, E.H., Lipinski, C.A., Thakker, D.R., Wang, B. (Eds.), Pharmaceutical Profiling in Drug Discovery for Lead Selection. AAPS Press, Arlington, Virginia, pp. 93-125.
    • (2004) Pharmaceutical Profiling in Drug Discovery for Lead Selection , pp. 93-125
    • Lipinski, C.A.1
  • 57
    • 80053505508 scopus 로고    scopus 로고
    • Coamorphous drug systems: Enhanced physical stability and dissolution rate of indomethacin and naproxen
    • Löbmann, K., Laitinen, R., Grohganz, H., Gordan, K.C., Strachan, C., Rades, T., 2011. Coamorphous drug systems: Enhanced physical stability and dissolution rate of indomethacin and naproxen. Mol. Pharm. 8, 1919-1928.
    • (2011) Mol. Pharm. , vol.8 , pp. 1919-1928
    • Löbmann, K.1    Laitinen, R.2    Grohganz, H.3    Gordan, K.C.4    Strachan, C.5    Rades, T.6
  • 58
    • 84861092839 scopus 로고    scopus 로고
    • Coamorphous simvastatin and glipizide combinations show improved physical stability without evidence of intermolecular interactions
    • Löbmann, K., Strachan, C., Grohganz, H., Rades, T., Korhonen, O., Laitinen, R., 2012. Coamorphous simvastatin and glipizide combinations show improved physical stability without evidence of intermolecular interactions. Eur. J. Pharm. Biopharm. 81, 159-169.
    • (2012) Eur. J. Pharm. Biopharm. , vol.81 , pp. 159-169
    • Löbmann, K.1    Strachan, C.2    Grohganz, H.3    Rades, T.4    Korhonen, O.5    Laitinen, R.6
  • 60
    • 80052963861 scopus 로고    scopus 로고
    • Computational prediction of salt and cocrystal structures-Does a proton position matter?
    • Mohamed, S., Tocher, D.A., Price, S.L., 2011. Computational prediction of salt and cocrystal structures-Does a proton position matter? Int. J. Pharm. 418, 187-198.
    • (2011) Int. J. Pharm. , vol.418 , pp. 187-198
    • Mohamed, S.1    Tocher, D.A.2    Price, S.L.3
  • 64
    • 0035897679 scopus 로고    scopus 로고
    • Theoretical approaches to physical transformations of active pharmaceutical ingredients during manufacturing processes
    • DOI 10.1016/S0169-409X(01)00100-4, PII S0169409X01001004
    • Morris, K.R., Griesser, U.J., Eckhardt, C.J., Stowell, J.G., 2001. Theoretical approaches to physical transformations of active pharmaceutical ingredients during manufacturing processes. Adv. Drug Del. Rev. 48, 91-114. (Pubitemid 32452293)
    • (2001) Advanced Drug Delivery Reviews , vol.48 , Issue.1 , pp. 91-114
    • Morris, K.R.1    Griesser, U.J.2    Eckhardt, C.J.3    Stowell, J.G.4
  • 65
    • 79957979325 scopus 로고    scopus 로고
    • Polymorphs, pseudopolymorphs, and co-crystals of orcinol: Exploring the structural landcape with high throughput crystallography
    • Mukherjee, A., Grobelny, P., Thakur, T.S., Desiraju, G.R., 2011. Polymorphs, pseudopolymorphs, and co-crystals of orcinol: Exploring the structural landcape with high throughput crystallography. Cryst. Growth Des. 11, 2637-2653.
    • (2011) Cryst. Growth Des. , vol.11 , pp. 2637-2653
    • Mukherjee, A.1    Grobelny, P.2    Thakur, T.S.3    Desiraju, G.R.4
  • 66
    • 0002642747 scopus 로고
    • Theorie der reaktionsgeschwindigkeit in heterogenen systemen
    • Nernst, W., 1904. Theorie der reaktionsgeschwindigkeit in heterogenen systemen. Z. Phys. Chem. 47, 52-55.
    • (1904) Z. Phys. Chem. , vol.47 , pp. 52-55
    • Nernst, W.1
  • 67
    • 15744376252 scopus 로고    scopus 로고
    • Electron and nuclear positions in the short hydrogen bond in urotropine-N-oxide-formic acid
    • DOI 10.1021/jp047187r
    • Nygren, C.L., Wilson, C.C., Turner, J.F.C., 2005. Electron and nuclear positions in the short hydrogen bond in utropine-N-oxide-formic acid. J. Phys. Chem. A 109, 1911-1919. (Pubitemid 40406841)
    • (2005) Journal of Physical Chemistry A , vol.109 , Issue.9 , pp. 1911-1919
    • Nygren, C.L.1    Wilson, C.C.2    Turner, J.F.C.3
  • 68
    • 0035845754 scopus 로고    scopus 로고
    • Preparation and characterisation of a range of diclofenac salts
    • DOI 10.1016/S0378-5173(01)00800-6, PII S0378517301008006
    • O'Connor, K.M., Corrigan, O.W., 2001. Preparation and characterization of a range of diclofenac salts. Int. J. Pharm. 226, 163-179. (Pubitemid 32800791)
    • (2001) International Journal of Pharmaceutics , vol.226 , Issue.1-2 , pp. 163-179
    • O'Connor, K.M.1    Corrigan, O.I.2
  • 72
    • 33645115596 scopus 로고    scopus 로고
    • Polymorphism, salts, and crystallization: The relevance of solid state development
    • Raumer, V.M., Dannappel, J., Hilfiker, R., 2006. Polymorphism, salts, and crystallization: the relevance of solid state development. Chem. Today 24, 41-44.
    • (2006) Chem. Today , vol.24 , pp. 41-44
    • Raumer, V.M.1    Dannappel, J.2    Hilfiker, R.3
  • 75
    • 65449130073 scopus 로고    scopus 로고
    • Synthon competition and cooperation in molecular salts of hydroxybenzoic acids and aminopyridines
    • Sarma, B., Nath, N.K., Bhogala, B.R., Nangia, A., 2009. Synthon competition and cooperation in molecular salts of hydroxybenzoic acids and aminopyridines. Cryst. Growth Des. 9, 1546-1557.
    • (2009) Cryst. Growth Des. , vol.9 , pp. 1546-1557
    • Sarma, B.1    Nath, N.K.2    Bhogala, B.R.3    Nangia, A.4
  • 76
    • 66849083715 scopus 로고    scopus 로고
    • Pharmaceutical cocrystals and their physicochemical properties
    • Schultheiss, N., Newman, A., 2009. Pharmaceutical cocrystals and their physicochemical properties. Cryst. Growth Des. 9, 2950-2967.
    • (2009) Cryst. Growth Des. , vol.9 , pp. 2950-2967
    • Schultheiss, N.1    Newman, A.2
  • 77
    • 34548032742 scopus 로고    scopus 로고
    • Salt formation to improve drug solubility
    • DOI 10.1016/j.addr.2007.05.010, PII S0169409X07000816
    • Serajuddin, A.T.M., 2007. Salt formation to improve drug solubility. Adv. Drug Del. Rev. 59, 603-616. (Pubitemid 47285406)
    • (2007) Advanced Drug Delivery Reviews , vol.59 , Issue.7 , pp. 603-616
    • Serajuddin, A.T.M.1
  • 78
    • 0032885450 scopus 로고    scopus 로고
    • Solid dispersions of poorly water soluble drugs: Early promises, subsequent problems and recent breakthroughs
    • Serajuddin, A.T., 1999. Solid dispersions of poorly water soluble drugs: Early promises, subsequent problems and recent breakthroughs. J. Pharm. Sci. 88, 1058-1066.
    • (1999) J. Pharm. Sci. , vol.88 , pp. 1058-1066
    • Serajuddin, A.T.1
  • 79
    • 0021944082 scopus 로고
    • Effect of diffusion layer pH and solubility on the dissolution rate of pharmaceutical acids and their sodium salts II: Salicylic acid, theophylline, and benzoic acid
    • DOI 10.1002/jps.2600740209
    • Serajuddin, A.T.M., Jarowski, C.I., 1985. Effect of diffusion layer pH and solubility on the dissolution rate of pharmaceutical acids and their sodium salts II: salicylic acid, theophyline and benzoic acid. J. Pharm. Sci. 74, 148-154. (Pubitemid 15135800)
    • (1985) Journal of Pharmaceutical Sciences , vol.74 , Issue.2 , pp. 148-154
    • Serajuddin, A.T.M.1    Jarowski, C.I.2
  • 80
    • 0021946116 scopus 로고
    • pH-solubility profiles of organic bases and their hydrochloride salts
    • Serajuddin, A.T.M., Mufson, D., 1985. pH-Solubility profiles of organic bases and their hydrochloride salts. Pharm. Res. 2, 65-68. (Pubitemid 15123844)
    • (1985) Pharmaceutical Research , vol.NO. 2 , pp. 65-68
    • Serajuddin, A.T.M.1    Mufson, D.2
  • 82
    • 0023198501 scopus 로고
    • Common ion effect on solubility and the dissolution rate of the sodium salt of an organic acid
    • Serajuddin, A.T.M., Sheen, P.C., Augustine, M.A., 1987. Common ion effect on the solubility and dissolution rate of the sodium salt of an organic acid. J. Pharm. Pharmacol. 39, 587-591. (Pubitemid 17116301)
    • (1987) Journal of Pharmacy and Pharmacology , vol.39 , Issue.8 , pp. 587-591
    • Serajuddin, A.T.M.1    Sheen, P.-C.2    Augustine, M.A.3
  • 83
    • 68449100594 scopus 로고    scopus 로고
    • Antidepressants as hydrobromide salts: Are they a cause for concern?
    • Shader, R.I., 2009. Antidepressants as hydrobromide salts: Are they a cause for concern? J. Clin. Pyschopharm. 29, 317-318.
    • (2009) J. Clin. Pyschopharm. , vol.29 , pp. 317-318
    • Shader, R.I.1
  • 84
    • 84855404945 scopus 로고    scopus 로고
    • Advances in pharmaceutical co-crystal screening: Effective co-crystal screening through structural resemblance
    • Springuel, G., Norberg, B., Robeyns, K., Wouters, J., Leyssens, T., 2012. Advances in pharmaceutical co-crystal screening: Effective co-crystal screening through structural resemblance. Cryst. Growth Des. 12, 475-484.
    • (2012) Cryst. Growth Des. , vol.12 , pp. 475-484
    • Springuel, G.1    Norberg, B.2    Robeyns, K.3    Wouters, J.4    Leyssens, T.5
  • 85
    • 1042273375 scopus 로고    scopus 로고
    • Pharmaceutical aspects of the drug salt form
    • Stahl, P.H., Wermuth, G. (Eds.), Wiley-VCH, Weinheim
    • Stahl, P.H., Nakano, M., 2002. Pharmaceutical aspects of the drug salt form. In: Stahl, P.H., Wermuth, G. (Eds.), Handbook of Pharmaceutical Salts; Properties, Selection and Use. Wiley-VCH, Weinheim, pp. 83-116.
    • (2002) Handbook of Pharmaceutical Salts; Properties, Selection and Use , pp. 83-116
    • Stahl, P.H.1    Nakano, M.2
  • 88
    • 34347245300 scopus 로고    scopus 로고
    • Diversity in single- and multiple-component crystals. The search for and prevalence of polymorphs and co-crystals
    • Stahly, G.P., 2007. Diversity in single- and multiple-component crystals. The search for and prevalence of polymorphs and co-crystals. Cryst. Growth Des. 7, 1007-1026.
    • (2007) Cryst. Growth Des. , vol.7 , pp. 1007-1026
    • Stahly, G.P.1
  • 89
    • 79955594268 scopus 로고    scopus 로고
    • Improved pharmacokinetics of AMG 517 through co-crystallization Part 2: Analysis of 12 carboxylic acid co-crystals
    • Stanton, M.K., Kelly, R.C., Colletti, A., Langley, M., Munson, E.J., Peterson, M.L., Roberts, J., Wells, M., 2011. Improved pharmacokinetics of AMG 517 through co-crystallization Part 2: Analysis of 12 carboxylic acid co-crystals. J. Pharm. Sci. 100, 2734-2743.
    • (2011) J. Pharm. Sci. , vol.100 , pp. 2734-2743
    • Stanton, M.K.1    Kelly, R.C.2    Colletti, A.3    Langley, M.4    Munson, E.J.5    Peterson, M.L.6    Roberts, J.7    Wells, M.8
  • 90
    • 79952224350 scopus 로고    scopus 로고
    • Physical stability of salts of weak bases in the solid-state
    • Stephenson, G.A., Arurub, A., Woods, T.A., 2011. Physical stability of salts of weak bases in the solid-state. J. Pharm. Sci. 100, 1607-1617.
    • (2011) J. Pharm. Sci. , vol.100 , pp. 1607-1617
    • Stephenson, G.A.1    Arurub, A.2    Woods, T.A.3
  • 91
    • 67049162360 scopus 로고    scopus 로고
    • Improved physical stability of amorphous state through acid base interactions
    • Telang, C., Mujumdar, S., Mathew, M., 2009. Improved physical stability of amorphous state through acid base interactions. J. Pharm. Sci. 98, 2149-2159.
    • (2009) J. Pharm. Sci. , vol.98 , pp. 2149-2159
    • Telang, C.1    Mujumdar, S.2    Mathew, M.3
  • 92
    • 0032815782 scopus 로고    scopus 로고
    • Solid-state characteristics of amorphous sodium indomethacin relative to its free acid
    • DOI 10.1023/A:1018985110956
    • Tong, P., Zografi, G., 1999. Solid-state characteristics of amorphous sodium indomethacin relative to its free acid. Pharm. Res. 16, 1186-1192. (Pubitemid 29393605)
    • (1999) Pharmaceutical Research , vol.16 , Issue.8 , pp. 1186-1192
    • Tong, P.1    Zografi, G.2
  • 93
    • 0036001407 scopus 로고    scopus 로고
    • Influence of alkali metal counterions on the glass transition temperature of amorphous indomethacin salts
    • DOI 10.1023/A:1015310213887
    • Tong, P., Taylor, L.S., Zografi, G., 2002. Influence of alkali metal counterions on the glass transition temperature of amorphous indomethacin salts. Pharm. Res. 19, 649-654. (Pubitemid 34553673)
    • (2002) Pharmaceutical Research , vol.19 , Issue.5 , pp. 649-654
    • Tong, P.1    Taylor, L.S.2    Zografi, G.3
  • 94
    • 64649101109 scopus 로고    scopus 로고
    • An investigation into the influence of counterion on the properties of some amorphous organic salts
    • Towler, C.S., Li, T., Wikstrom, H., Remick, D.M., Sanchez-Felix, M.V., Taylor, L.S., 2008. An investigation into the influence of counterion on the properties of some amorphous organic salts. Mol. Pharm. 5, 946-955.
    • (2008) Mol. Pharm. , vol.5 , pp. 946-955
    • Towler, C.S.1    Li, T.2    Wikstrom, H.3    Remick, D.M.4    Sanchez-Felix, M.V.5    Taylor, L.S.6
  • 97
    • 1642457350 scopus 로고    scopus 로고
    • An Automated Approach to Salt Selection for New Unique Trazodone Salts
    • DOI 10.1023/B:PHAM.0000012167.60180.c3
    • Ware, E.C., Lu, D.R., 2005. An automated approach to salt selection for new unique trazodone salts. Pharm. Res. 21, 177-184. (Pubitemid 38122307)
    • (2004) Pharmaceutical Research , vol.21 , Issue.1 , pp. 177-184
    • Ware, E.C.1    Lu, D.R.2
  • 99
    • 20744433869 scopus 로고    scopus 로고
    • Salt formation in solid dispersions consisting of polyacrylic acid as a carrier and three basic model compounds resulting in very high glass transition temperatures and constant dissolution properties upon storage
    • DOI 10.1016/j.ejps.2005.04.011, PII S0928098705001351
    • Weuts, I., Kempen, D., Verreck, G., Peeters, J., Brewster, M., Blsaton, M., Van den Mooter, G., 2005. Salt formation in solid dispersions consisting of polyacrylic acid as a carrier and three basic model compounds resulting in very high glass transition temperatures and constant dissolution properties upon storage. Eur. J. Pharm. Sci. 25, 387-393. (Pubitemid 40853866)
    • (2005) European Journal of Pharmaceutical Sciences , vol.25 , Issue.4-5 , pp. 387-393
    • Weuts, I.1    Kempen, D.2    Verreck, G.3    Peeters, J.4    Brewster, M.5    Blaton, N.6    Van Den, M.G.7
  • 100
    • 0035991618 scopus 로고    scopus 로고
    • Examination of the solubilization of drugs by bile salt micelles
    • DOI 10.1002/jps.10158
    • Wiedmann, T.S., Kamel, L., 2002. Examination of the solubilisation of drugs by bile salt micelles. J. Pharm. Sci. 91, 1743-1764. (Pubitemid 34810521)
    • (2002) Journal of Pharmaceutical Sciences , vol.91 , Issue.8 , pp. 1743-1764
    • Wiedmann, T.S.1    Kamel, L.2
  • 101
    • 0019166075 scopus 로고
    • Solubility and partitioning I. Solubility of nanoelectrolytes in water
    • Yalkowsky, S.H., Valvani, S.C., 1980. Solubility and partitioning I. Solubility of nanoelectrolytes in water. J. Pharm. Sci. 68, 912-922.
    • (1980) J. Pharm. Sci. , vol.68 , pp. 912-922
    • Yalkowsky, S.H.1    Valvani, S.C.2
  • 102
    • 27744509918 scopus 로고    scopus 로고
    • Measuring free-energy difference between crystal polymorphs through eutectic melting
    • DOI 10.1021/jp053653g
    • Yu, L., Huang, J., Jones, K.J., 2005. Measuring free energy differences between crystal polymorphs through eutectic melting. J. Phys. Chem. B 109, 19915-19922. (Pubitemid 41598505)
    • (2005) Journal of Physical Chemistry B , vol.109 , Issue.42 , pp. 19915-19922
    • Yu, L.1    Huang, J.2    Jones, K.J.3
  • 103
    • 34248596026 scopus 로고    scopus 로고
    • Stabilization of the maleate salt of a basic drug by adjustment of microenvironmental pH in solid dosage form
    • DOI 10.1016/j.ijpharm.2007.01.005, PII S0378517307000178
    • Zannou, E.A., Ji, Q., Joshi, Y.M., Serajuddin, A.T.M., 2007. Stabilization of the maleate salt of a basic drug by adjustment of the microenvironment pH in the solid dosage form. Int. J. Pharm. 337, 210-218. (Pubitemid 46756053)
    • (2007) International Journal of Pharmaceutics , vol.337 , Issue.1-2 , pp. 210-218
    • Zannou, E.A.1    Ji, Q.2    Joshi, Y.M.3    Serajuddin, A.T.M.4
  • 104
    • 0034936439 scopus 로고    scopus 로고
    • Dehydration, hydration behavior, and structural analysis of fenoprofen calcium
    • DOI 10.1002/jps.1038
    • Zhu, H., Xu, J., Varlashkin, P., Long, S., Kidd, C., 2001. Dehydration, hydration behaviour and structural analysis of fenoprofen calcium. J. Pharm. Sci. 90, 845-859. (Pubitemid 32645943)
    • (2001) Journal of Pharmaceutical Sciences , vol.90 , Issue.7 , pp. 845-859
    • Zhu, H.1    Xu, J.2    Varlashkin, P.3    Long, S.4    Kidd, C.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.