Initial Salt Screening Procedures for Manufacturing Ibuprofen

REFERENCES

• S. Agharkar, S. Lindenbaum, and T. Higuchi. (1976). Enhancement of solubility of drug salts by hydrophilic counterions: Properties of organic salts of an antimalarial drug. J. Pharm. Sci. 65 (5):747–749.
   PubMed Web of Science ®Google Scholar
• J. Alsenz, and M. Kansy. (2007). High throughput solubility measurement in drug discovery and development. Adv. Drug Deliv. Rev. 59 (7):546–567.
   PubMed Web of Science ®Google Scholar
• B. J. Armitage, J. F. Lampard, and A. Smith. (2001). Composition of S(-) sodium ibuprofen. US Patent No. 6,242,000 B1.
   Google Scholar
• S. Balbach, and C. Korn. (2004). Pharmaceutical evaluation of early development candidates “the 100 mg-approach”. Int. J. Pharm. 275 (1–2):1–12.
   PubMed Web of Science ®Google Scholar
• A. F. M. Barton. (1991). Solvent scales. CRC handbook of solubility parameters and other cohesion parameters 2nd. Boston, USA: CRC Press, 294–295. chap. 8.
   Google Scholar
• R. J. Bastin, M. J. Bowker, and B. J. Slater. (2000). Salt selection and optimisation procedures for pharmaceutical new chemical entities. Org. Proc. Res. Dev. 4 (5):427–435.
   Web of Science ®Google Scholar
• S. M. Berge, L. D. Bighley, and D. C. Monkhouse. (1977). Pharmaceutical salts. J. Pharm. Sci. 66 (1):1–19.
   PubMed Web of Science ®Google Scholar
• S. N. Black, E. A. Collier, R. J. Davey, and R. J. Roberts. (2007). Structure, solubility, screening, and synthesis of molecular salts. J. Pharm. Sci. 96 (5):1053–1068.
   PubMed Web of Science ®Google Scholar
• T. Bruzzese, R. Ferrari, and SPA-Socita Prodotti Antibiotici. (1981). Method of relieving pain and treating inflammatory conditions in warm-blooded animals. US Patent No, 4279926.
   Google Scholar
• J. M. E. Bunyan, N. Shankland, and D. B. Sheen. (1991). Solvent effects on the morphology of ibuprofen. AIChE Symp. Ser. 87 (284):44–57.
   Google Scholar
• H. Cano, N. Gabas, and J. P. Canselier. (2001). Experimental study on the ibuprofen crystal growth morphology in solution. J. Cryst. Growth 224 (3–4):335–341.
   Web of Science ®Google Scholar
• E. D. Carlson, P. Cong, W. H. Chandler, Jr., P. J. Desrosiers, J. Christopher Freitag, J. F. Varni, and Symyx Technologies. (2005). Apparatuses and methods for creating and testing pre-formulations and systems for same. US Patent No. 6,939,515 B2.
   Google Scholar
• R. Chidambaram, G. M. Derbin, M. Endo, J. Gao, T. Lee, R. Motheram, W. L. Parker, V. W. Rosso, S. A. Varia, and Bristol-Myers Squibb. (2007). Oral Administration of N-(2-Chloro-6-Methylphenyl)-2-[[6-[4-(2-Hydroxyethyl)-1-Piper-Azinyl]-2-Methyl-4-Pyrimidinyl]Amino]-1,3-Thiazole-5-Carboxamide and Salts Thereof. WO 035874 A1:
   Google Scholar
• N. B. Colthup, L. H. Daly, and S. E. Wiberley. (1990a). Amines, C=N, and N=O compounds. Introduction to infrared and Raman spectroscopy, 3rd. San Diego, CA: Alexander Press, 340–343. chap. 11.
   Google Scholar
• N. B. Colthup, L. H. Daly, and S. E. Wiberley. (1990b). Carbonyl compounds. Introduction to infrared and Raman spectroscopy, 3rd. San Diego, CA: Alexander Press, 317–319. chap. 9.
   Google Scholar
• D. J. C. Constable, C. Jimenez-Gonzalez, and R. K. Henderson. (2007). Perspective on solvent use in the pharmaceutical industry. Org. Proc. Res. Dev. 11 (1):133–137.
   Web of Science ®Google Scholar
• D. Eilerman, and R. Rudman. (1980). Polymorphism of crystalline poly(hydroxymethyl) compounds. III. The structures of crystalline and plastic tris(hydroxymethyl)aminomethane. J. Chem. Phys. 72 (10):5656–5666.
   Web of Science ®Google Scholar
• G. L. Engel, N. A. Farid, M. M. Faul, L. A. Richardson, and L. L. Winneroski. (2000). Salt form selection and characterization of LY333531 mesylate monohydrate. Int. J. Pharm. 198 (2):239–247.
   PubMed Web of Science ®Google Scholar
• S. G. Fleischman, S. S. Kuduva, J. A. McMahon, B. Moulton, R. D. Bailey Walsh, N. Rodríguez-Hornedo, and M. J. Zaworotko. (2003). Crystal engineering of the composition of pharmaceutical phases: Multiple-component crystalline solids involving carbamazepine. Cryst. Growth Des. 3 (6):909–919.
   Web of Science ®Google Scholar
• A. A. Freer, J. M. Bunyan, N. Shankland, and D. B. Sheen. (1993). Structure of (S)-(+)-ibuprofen. Acta Cryst. C49:1378–1380.
   Google Scholar
• L. C. Garzón, and F. Martínez. (2004). Temperature dependence of solubility for ibuprofen in some organic and aqueous solvents. J. Sol. Chem. 33 (11):1379–1395.
   Web of Science ®Google Scholar
• P. L. Gould. (1986). Salt selection for basic drugs. Int. J. Pharm. 33 (1–3):201–217.
   Web of Science ®Google Scholar
• H.-S. Gwak, J.-S. Choi, and H.-K. Choi. (2005). Enhanced bioavailability of piroxicam via salt formation with ethanolamines. Int. J. Pharm. 297 (1-2):156–161.
   PubMedGoogle Scholar
• Hansen, L. Kr, G. L. Perlovich, and A. Bauer-Brandl. (2003). Redetermination and H-atom refinement of (S)-(+)-ibuprofen. Acta Cryst. E59 (9):o1357–o1358.
   Google Scholar
• S. J. Hehm, B. Rodríguez-Spong, and N. Rodríguez-Hornedo. (2006). Phase solubility diagrams of cocrystals are explained by solubility product and solution complexation. Cryst. Growth Des. 6 (2):592–600.
   Web of Science ®Google Scholar
• H. P. Jones, R. J. Davey, and B. G. Cox. (2005). Crystallization of a salt of a weak organic acid and base: Solubility relations, supersaturation control and polymorphic behavior. J. Phys. Chem. B 109 (11):5273–5278.
   PubMed Web of Science ®Google Scholar
• K. Kawakami, Y. Ida, and T. Yamaguchi. (2005). Effect of salt type on hygroscopicity of a new cephalosporin S-3578. Pharm. Res. 22 (8):1365–1373.
   PubMed Web of Science ®Google Scholar
• G. M. Khan, and Z. Jiabi. (1998). Preparation, characterization, and evaluation of physicochemical properties of different crystalline forms of ibuprofen. Drug Dev. Ind. Pharm. 24 (5):463–471.
   PubMed Web of Science ®Google Scholar
• S. Kim, C. Wei, and S. Kiang. (2003). Crystallization process development of an active pharmaceutical ingredient and particle engineering via the use of ultrasonics and temperature cycling. Org. Proc. Res. Dev. 7 (6):997–1001.
   Web of Science ®Google Scholar
• M. Klenell, P. Snoeijs, and M. Pedersén. (2004). Active carbon uptake in Laminaria digitata and L. saccharina (Phaeophyta) is driven by a proton pump in the plasma membrane. Hydrobiologia 514 (1–3):41–53.
   Web of Science ®Google Scholar
• L. Kumar, A. Amin, and A. K. Bansal. (2007). An overview of automated systems relevant in pharmaceutical salt screening. Drug Discov. Today 12 (23–24):1046–1053.
   PubMed Web of Science ®Google Scholar
• T. Lee, Y. H. Chen, and Y. W. Wang. (2008). Effects of homochiral molecules of (S)-(+)-ibuprofen and (S)-(?−)-sodium ibuprofen dihydrate on the crystallization kinetics of racemic (R,S)-(±)-sodium ibuprofen dehydrate. Cryst Growth Des. 8 (2):415–426.
   Web of Science ®Google Scholar
• T. Lee, Y. H. Chen, and C. W. Zhang. (2007). Solubility, polymorphism, crystallinity, crystal habit, and drying scheme of (R,S)-(±)-sodium ibuprofen dihydrate. Pharm. Tech. 31 (6):72–87.
   Google Scholar
• T. Lee, C. S. Kuo, and Y. H. Chen. (2006). Solubility, polymorphism, crystallinity, and crystal habit of acetaminophen and ibuprofen by initial solvent screening. Pharm. Tech. 30 (10):72–92.
   Google Scholar
• S. Li, S. Wong, S. Sethia, H. Almoazen, Y. M. Joshi, and A. T. M. Serajuddin. (2005). Investigation of solubility and dissolution of a free base and two different salt forms as a function of pH. Pharm. Res. 22 (4):628–635.
   PubMed Web of Science ®Google Scholar
• D. R. Lide. (2005). BiochemistryCRC handbook of chemistry and physics, 86th ed. Boston, MA: CRC Press, 7–1. sect. 7.
   Google Scholar
• P. D. Martino, M. Beccerica, E. Joiris, G. F. Palmieri, A. Gayot, and S. Martelli. (2002). Influence of crystal habit on the compression and the densification mechanism of ibuprofen. J. Cryst. Growth 243 (2):345–355.
   Web of Science ®Google Scholar
• S. L. Morissette, Ö. Almarsson, M. L. Paterson, J. F. Remenar, M. J. Read, A. V. Lemmo, S. Ellis, M. J. Cima, and C. R. Gardner. (2004). High-throughput crystallization: Polymorphs, salts, co-crystals and solvates of pharmaceutical solids. Adv. Drug Deliv. Rev. 56 (3):275–300.
   PubMed Web of Science ®Google Scholar
• K. R. Morris, M. G. Fakes, A. B. Thakur, A. W. Newman, A. K. Singh, J. J. Venit, C. J. Spagnuolo, and A. T. M. Serajuddin. (1994). An integrated approach to the selection of optimal salt form for a new drug candidate. Int. J. Pharm. 105 (3):209–217.
   Web of Science ®Google Scholar
• A. H. Nada, S. M. Al-Saidan, and B. W. Mueller. (2005). Improving the physical and chemical properties of ibuprofen. Pharm. Tech. 29 (11):90–101.
   Google Scholar
• L. M. Oberoi, K. S. Alexander, and A. T. Riga. (2005). Study of interaction between ibuprofen and nicotinamide using differential scanning calorimetry, spectroscopy, and microscopy and formulation of a fast-acting and possibly better ibuprofen suspension for osteoarthritis patients. J. Pharm. Sci. 94 (1):93–101.
   PubMed Web of Science ®Google Scholar
• G. L. Perlovich, S. V. Kurkov, L. K. Hansen, and A. Bauer-Brandl. (2004). Thermodynamics of sublimation, crystal lattice energies, and crystal structures of racemates and enantiomers: (+)- And (±)-ibuprofen. J. Pharm. Sci. 93 (3):654–666.
   PubMed Web of Science ®Google Scholar
• N. Rasenack, and B. W. Müller. (2002). Properties of ibuprofen crystallized under various conditions: A comparative study. Drug Dev. Ind. Pharm. 28 (9):1077–1089.
   PubMed Web of Science ®Google Scholar
• J. F. Remenar, S. L. Morissette, M. L. Peterson, B. Moulton, J. Michael MacPhee, H. R. Guzmán, and Ö. Almarson. (2003). Crsytal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids. J. Am. Chem. Soc. 125 (28):8456–8458.
   PubMed Web of Science ®Google Scholar
• N. Rodríguez-Hornedo, and D. Murphy. (2004). Surfactant-facilitated crystallization of dihydrate carbamazepine during dissolution of anhydrous polymorph. J. Pharm. Sci. 93 (2):449–460.
   PubMed Web of Science ®Google Scholar
• A. J. Romero, and C. T. Rhodes. (1991). Approaches to stereospecific preformulation of ibuprofen. Drug Dev. Ind. Pharm. 17 (5):777–792.
   Web of Science ®Google Scholar
• A. J. Romero, L. Savastano, and C. T. Rhodes. (1993). Monitoring crystal modifications in systems containing ibuprofen. Int. J. Pharm. 99 (2-3):125–134.
   Web of Science ®Google Scholar
• B. Sádaba, M. A. Campanero, M. J. Muñoz-JuarezGil-Aldea, I. García-Quetglas, E. A. Esteras, and J. R. Azanza. (2006). A comparative study of the pharmacokinetics of ibuprofen arginate versus dexibuprofen in healthy volunteers. Eur. J. Clin. Pharmacol. 62 (10):849–854.
   PubMed Web of Science ®Google Scholar
• A. T. M. Serajuddin. (2007). Salt formation to improve drug solubility. Adv. Drug Deliv. Rev. 59 (7):603–616.
   PubMed Web of Science ®Google Scholar
• K. Shankland, W. I. F. David, T. Csoka, and L. McBride. (1998). Structure solution of ibuprofen from powder diffraction data by the application of a generic algorithm combined with prior conformational analysis. Int. J. Pharm. 165 (1):117–126.
   Web of Science ®Google Scholar
• N. Shankland, C. C. Wilson, A. J. Florence, and P. J. Cox. (1997). Refinement of ibuprofen at 100 k by single-crystal pulsed neutron diffraction. Acta Cryst. C53:951–954.
   Google Scholar
• W. Sorasuchart, J. Wardrop, and J. W. Ayres. (1999). Drug release from spray layered and coated drug-containing beads: Effects of pH and comparison of different dissolution methods. Drug Dev. Ind. Pharm. 25 (10):1093–1098.
   PubMed Web of Science ®Google Scholar
• G. Steffen Paulekuhn, J. B. Dressman, and C. Saal. (2007). Trends in active pharmaceutical ingredient salt selection based on analysis of the orange book database. J. Med. Chem 50 (26):6665–6672.
   PubMed Web of Science ®Google Scholar
• K. Terashima, S. Kageyama, H. Katsuyama, and Fuji Photo Film Co., Ltd. (1990). Integral multilayer analytical element for use in the measurement of alkaline phosphatase activity. US Patent No. 4,900,665.
   Google Scholar
• A. V. Trask, D. A. Haynes, W. D. Samual Motherwell, and W. Jones. (2006). Screening for crystalline salts via mechanochemistry. Chem. Commun. 51–53.
   PubMed Web of Science ®Google Scholar
• D. Winn, and M. F. Doherty. (1998). A new technique for predicting the shape of solution-grown organic crystals. AIChE J. 44 (11):2501–2514.
   Web of Science ®Google Scholar
• Y. Zhang, and D. J. W. Grant. (2005). Similarity in structures of racemic and enantiomeric ibuprofen sodium dihydrates. Acta Cryst. C61:m435–m438.
   Google Scholar