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Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients
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Vishweshwar, P.; McMahon, J. A.; Peterson, M. L.; Hickey, M. B.; Shattock, T. R.; Zaworotko, M. J. Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients. Chem. Commun. 2005, 4601-4603.
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Sokolov, A. N.; Friščić, T.; MacGillivray, L. R. Enforced Face-to-Face Stacking of Organic Semiconductor Building Blocks within Hydrogen-Bonded Molecular Cocrystals. J. Am. Chem. Soc. 2006, 128, 2806-2807.
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Sokolov, A. N.; Friščić, T.; MacGillivray, L. R. Enforced Face-to-Face Stacking of Organic Semiconductor Building Blocks within Hydrogen-Bonded Molecular Cocrystals. J. Am. Chem. Soc. 2006, 128, 2806-2807.
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Reversing the code of a template-directed solid-state synthesis: A bipyridine template that directs a single-crystal-to-single-crystal [2+2] photodimerisation of a dicarboxylic acid
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Friscic, T.; MacGillivray, L. R.. Reversing the code of a template-directed solid-state synthesis: a bipyridine template that directs a single-crystal-to-single-crystal [2+2] photodimerisation of a dicarboxylic acid. Chem. Commun. 2005, 5748-5750.
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Modularity in organic solid state and supramolecular chemistry
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Friščić, T.; MacGillivray, L. R. Modularity in organic solid state and supramolecular chemistry. Croat. Chem. Acta 2006, 79, 327-333.
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Total synthesis supramolecular style: Design and hydrogen-bond-directed assembly of ternary supermolecules
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Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. "Total synthesis" supramolecular style: design and hydrogen-bond-directed assembly of ternary supermolecules. Angew. Chem., Int. Ed. 2001, 40, 3240-3242.
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Aakeröy, C.B.1
Beatty, A.M.2
Helfrich, B.A.3
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7
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33746899402
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Use of a Glutaric Acid Cocrystal to Improve Oral Bioavailability of a Low Solubility API
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McNamara, D. P.; Childs, S. L.; Giordano, J.; Iarriccio, A.; Cassidy, J.; Shet, M. S.; Mannion, R.; O'Donnel, E.; Park, A. Use of a Glutaric Acid Cocrystal to Improve Oral Bioavailability of a Low Solubility API. Pharm. Res. 2006, 23, 1888-1897.
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McNamara, D.P.1
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Cassidy, J.5
Shet, M.S.6
Mannion, R.7
O'Donnel, E.8
Park, A.9
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32644436069
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Phase Solubility Diagrams of Cocrystals Are Explained by Solubility Product and Solution Complexation
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Nehm, S. J.; Rodriguez-Spong, B.; Rodriguez-Hornedo, N. Phase Solubility Diagrams of Cocrystals Are Explained by Solubility Product and Solution Complexation. Cryst. Growth Des. 2006, 6, 592-600.
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Nehm, S.J.1
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Rodriguez-Hornedo, N.3
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9
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33746425242
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Physical stability enhancement of theophylline via cocrystallization
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Trask, A. V.; Motherwell, W. D. S.; Jones, W. Physical stability enhancement of theophylline via cocrystallization. Int. J. Pharm. 2006, 320, 114-123.
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Trask, A.V.1
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Pharmaceutical Cocrystallization: Engineering a Remedy for Caffeine Hydration
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Trask, A. V.; Motherwell, W. D. S.; Jones, W. Pharmaceutical Cocrystallization: Engineering a Remedy for Caffeine Hydration. Cryst. Growth Des. 2005, 5, 1013-1021.
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Pharmaceutical co-crystals
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Vishweshwar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. Pharmaceutical co-crystals. J. Pharm. Sci. 2006, 95, 499-516.
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McMahon, J.A.2
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0034981295
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Molecular complexes between 2,2′- biphenyldicarboxylic acid and phenazine: Anhydrous and hydrated forms
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Shaameri, Z.; Jones, W. Molecular complexes between 2,2′- biphenyldicarboxylic acid and phenazine: anhydrous and hydrated forms. Mol. Cryst. Liq. Cryst. 2001, 356, 131-142.
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Crystal engineering of organic cocrystals by the solid-state grinding approach
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Trask, A. V.; Jones, W. Crystal engineering of organic cocrystals by the solid-state grinding approach. Top. Curr. Chem. 2005, 254, 41-70.
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Crystal engineering using co-crystallisation of phenazine with dicarboxylic acids
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Batchelor, E.; Klinowski, J.; Jones, W. Crystal engineering using co-crystallisation of phenazine with dicarboxylic acids. J. Mater. Chem. 2000, 10, 839-848.
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Klinowski, J.2
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Cocrystal Formation during Cogrinding and Storage is Mediated by Amorphous Phase
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Jayasankar, A.; Somwangthanaroj, A.; Shao, Z. J.; Rodriguez-Hornedo, N. Cocrystal Formation during Cogrinding and Storage is Mediated by Amorphous Phase. Pharm. Res. 2006, 23, 2381-2392.
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33845270213
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Exploring cocrystal-cocrystal reactivity via liquid-assisted grinding: Assembling of racemic and dismantling of enantiomeric cocrystals
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Friščić, T.; Fábián, L.; Burley, J. C.; Jones, W.; Motherwell, W. D. S. Exploring cocrystal-cocrystal reactivity via liquid-assisted grinding: assembling of racemic and dismantling of enantiomeric cocrystals. Chem. Commun. 2006, 5009-5011.
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33845204296
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Screening for Inclusion Compeounds and Systematic Construction of Three-Component Solids by Liquid-Assisted Grinding
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Friǧčić;, T.; Trask, A. V.; Jones, W.; Motherwell, W. D. S. Screening for Inclusion Compeounds and Systematic Construction of Three-Component Solids by Liquid-Assisted Grinding. Angew. Chem., Int. Ed. 2006, 45, 7546-7550.
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Trask, A.V.2
Jones, W.3
Motherwell, W.D.S.4
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34250868988
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A search of the 2006 Cambridge Structural Database (version 5.27) for structures of organic compounds of citric acid revealed three structures, CCDC reference codes: CITARC, CITRAC10, XOB-HIF.
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A search of the 2006 Cambridge Structural Database (version 5.27) for structures of organic compounds of citric acid revealed three structures, CCDC reference codes: CITARC, CITRAC10, XOB-HIF.
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19
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34250883903
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Dissociation pressures of citric acid monohydrate
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Melia, T. P. Dissociation pressures of citric acid monohydrate. Trans. Faraday Soc. 1964, 60, 1286-1288.
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Melia, T.P.1
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0346274284
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Heat of combustion of citric acid monohydrate
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Chappel, F. P.; Hoare, F. E. Heat of combustion of citric acid monohydrate. Trans. Faraday Soc. 1958, 54, 367-371.
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Chappel, F.P.1
Hoare, F.E.2
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21
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0034046754
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The cocrystal of caffeine and citric acid is probably the caffeine citrate used in treatment of apnea: Bhatia, J. Current options in the management of apnea of prematurity. Clin. Pediatr. 2000, 39, 327-336.
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The cocrystal of caffeine and citric acid is probably the "caffeine citrate" used in treatment of apnea: Bhatia, J. Current options in the management of apnea of prematurity. Clin. Pediatr. 2000, 39, 327-336.
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0037471461
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Identification of supramolecular templates: Design of solid-state photoreactivity using structural similarity
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Shan, N.; Jones, W. Identification of supramolecular templates: design of solid-state photoreactivity using structural similarity. Tetrahedron Lett. 2003, 44, 3687-3689.
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Tetrahedron Lett
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Shan, N.1
Jones, W.2
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23
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0036502189
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Crystal engineering using 4,4′-bipyridyl with di- and tricarboxylic acids
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Shan, N.; Bond, A. D.; Jones, W. Crystal engineering using 4,4′-bipyridyl with di- and tricarboxylic acids. Cryst. Eng. 2002, 5, 9-24.
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Cryst. Eng
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Shan, N.1
Bond, A.D.2
Jones, W.3
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24
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0036746781
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The mechanochemical formation of caffeine and theophylline hydrates has been previously reported during wet granulation of corresponding anhydrates: Jorgensen, A, Rantanen, J, Karjalainen, M, Khriachtchev, L, Raesaenen, E, Ylirousi, J. Hydrate Formation During Wet Granulation Studied by Spectroscopic Methods and Multivariate Analysis. Pharm. Res. 2002, 19, 1285-1291
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The mechanochemical formation of caffeine and theophylline hydrates has been previously reported during wet granulation of corresponding anhydrates: Jorgensen, A.; Rantanen, J.; Karjalainen, M.; Khriachtchev, L.; Raesaenen, E.; Ylirousi, J. Hydrate Formation During Wet Granulation Studied by Spectroscopic Methods and Multivariate Analysis. Pharm. Res. 2002, 19, 1285-1291.
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25
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0344687070
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Metamorphosis of caffeine hydrate and anhydrous caffeine
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Edwards, H. G. M.; Lawson, E.; de Matas, M.; Shields, L.; York, P. Metamorphosis of caffeine hydrate and anhydrous caffeine. J. Chem. Soc., Perkin Trans. 1997, 2, 1985-1990.
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J. Chem. Soc., Perkin Trans
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Edwards, H.G.M.1
Lawson, E.2
de Matas, M.3
Shields, L.4
York, P.5
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26
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0141521912
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Theophylline monohydrate
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CCDC reference code: THEOPH01
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Sun, C.; Zhou, D.; Grant, D. J. W.; Young, V. G., Jr. Theophylline monohydrate. Acta Crystallogr. 2002, E58, o368-o370. CCDC reference code: THEOPH01.
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(2002)
Acta Crystallogr
, vol.E58
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Sun, C.1
Zhou, D.2
Grant, D.J.W.3
Young Jr., V.G.4
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27
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34250897409
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2O. Cryst. Struct. Commun. 1972, 1, 23-6. CCDC reference code: CITARC.
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2O. Cryst. Struct. Commun. 1972, 1, 23-6. CCDC reference code: CITARC.
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28
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0014677813
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X-ray crystal analysis of the substrates of aconitase. IX. A refinement of the structure of anhydrous citric acid
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CCDC reference code: CITRAC10
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Glusker, J. P; Minkin, J. A.; Patterson, A. L. X-ray crystal analysis of the substrates of aconitase. IX. A refinement of the structure of anhydrous citric acid. Acta Crystallogr. 1969, B25, 1066-1072. CCDC reference code: CITRAC10.
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(1969)
Acta Crystallogr
, vol.B25
, pp. 1066-1072
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Glusker, J.P.1
Minkin, J.A.2
Patterson, A.L.3
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29
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34250845026
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Inspection of PXRD patterns reveals that neat grinding of anhydrous caffeine (β-form) with citric acid resulted in a partial conversion to α-caffeine
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Inspection of PXRD patterns reveals that neat grinding of anhydrous caffeine (β-form) with citric acid resulted in a partial conversion to α-caffeine.
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30
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34250903620
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Exposure of 3 to 98% relative humidity conditions results in the formation of a sticky solid. Inspection of the solid using XRPD reveals the presence of only solid caffeine hydrate, suggesting that citric acid is contained in the liquid phase.
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Exposure of 3 to 98% relative humidity conditions results in the formation of a sticky solid. Inspection of the solid using XRPD reveals the presence of only solid caffeine hydrate, suggesting that citric acid is contained in the liquid phase.
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37049076059
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For the only previous example where caffeine acts as a 3-fold hydrogen bond acceptor toward OH donors, see: Martin, R.; Lilley, T. H.; Bailey, N. A.; Falshaw, C. P.; Haslam, E.; Magnolato, D.; Begley, M. J. Polyphenol-Caffeine Complexation. Chem. Commun. 1986, 105-106. CCDC reference code: DIJWAU.
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For the only previous example where caffeine acts as a 3-fold hydrogen bond acceptor toward OH donors, see: Martin, R.; Lilley, T. H.; Bailey, N. A.; Falshaw, C. P.; Haslam, E.; Magnolato, D.; Begley, M. J. Polyphenol-Caffeine Complexation. Chem. Commun. 1986, 105-106. CCDC reference code: DIJWAU.
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34250872281
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The formation of cocrystal hydrates by crystallization from solution has previously been observed; see: Zaitu, S, Miwa, Y, Taga, T. A 2:1 Molecular Complex of Theophylline and 5-Fluorouracil as the Monohydrate. Acta Crystallogr. 1995, C51, 1857-1859. CCDC reference code: ZAYLOA
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The formation of cocrystal hydrates by crystallization from solution has previously been observed; see: Zaitu, S.; Miwa, Y.; Taga, T. A 2:1 Molecular Complex of Theophylline and 5-Fluorouracil as the Monohydrate. Acta Crystallogr. 1995, C51, 1857-1859. CCDC reference code: ZAYLOA
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0037168237
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Application of Slurry Bridging Experiments at Controlled Water Activities to Predict the Solid-State Conversion between Anhydrous and Hydrated Forms Using Theophylline as a Model Drug
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Ticehurst, M. D.; Storey, R. A.; Watt, C. Application of Slurry Bridging Experiments at Controlled Water Activities to Predict the Solid-State Conversion between Anhydrous and Hydrated Forms Using Theophylline as a Model Drug. Int. J. Pharm. 2002, 247, 1-10.
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Int. J. Pharm
, vol.247
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Ticehurst, M.D.1
Storey, R.A.2
Watt, C.3
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