Hydrochloride salt co-crystals: preparation, characterization and physicochemical studies

References

• Vippagunta SR, Brittain HG, Grant DJ. Crystalline solids. Adv Drug Deliv Rev 2001;48:3–26.
   PubMed Web of Science ®Google Scholar
• Haleblian JK. Characterization of habits and crystalline modification of solids and their pharmaceutical applications. J Pharm Sci 1975;64:1269–1288.
   PubMed Web of Science ®Google Scholar
• Sheth AR, Grant DJW. Relationship between the structure and properties of pharmaceutical crystals. KONA 2005;23:36–48.
   Web of Science ®Google Scholar
• Bernstein J. Polymorphism in molecular crystals. New York: Oxford University Press, 2002:4–6.
   Google Scholar
• Byrn SR, Pfeiffer RR, Stowell JG. Solid-state chemistry of drugs. Indiana: SSCI Inc 1999:10–15.
   Google Scholar
• Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ. Pharmaceutical co-crystals. J Pharm Sci 2006;95:499–516.
   PubMed Web of Science ®Google Scholar
• Shan N, Zaworotko MJ. The role of cocrystals in pharmaceutical science. Drug Discov Today 2008;13:440–446.
   PubMed Web of Science ®Google Scholar
• Yadav AV, Shete AS, Dabke AP, Kulkarni PV, Sakhare SS. Co-crystals: a novel approach to modify physicochemical properties of active pharmaceutical ingredients. Indian J Pharm Sci 2009;71:359–370.
   PubMed Web of Science ®Google Scholar
• Qiao N, Li M, Schlindwein W, Malek N, Davies A, Trappitt G. Pharmaceutical cocrystals: an overview. Int J Pharm 2011;419:1–11.
   PubMed Web of Science ®Google Scholar
• Aakeroy CB, Salmon DJ. Building co-crystals with molecular sense and supramolecular sensibility. Cryst Eng Comm 2005;7:439–448.
   Web of Science ®Google Scholar
• Morissette SL, Almarsson O, Peterson ML, Remenar JF, Read MJ, Lemmo AV et al. High-throughput crystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical solids. Adv Drug Deliv Rev 2004;56:275–300.
   PubMed Web of Science ®Google Scholar
• Trask AV, Motherwell WDS, Jones W. Pharmaceutical cocrystallization: Engineering a remedy for caffeine hydration. Cryst Growth Des 2005;5:1013–1021.
   Web of Science ®Google Scholar
• Childs SL, Chyall LJ, Dunlap JT, Smolenskaya VN, Stahly BC, Stahly GP. 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 2004;126:13335–13342.
   PubMed Web of Science ®Google Scholar
• Schultheiss N, Bethune S, Henck J. Nutraceutical cocrystals: utilizing pterostilbene as a cocrystal former. Cryst Eng Comm 2010;12:2436–2442.
   Google Scholar
• Cheney ML, Weyna DR, Shan N, Hanna M, Wojtas L, Zaworotko MJ. Coformer selection in pharmaceutical cocrystal development: a case study of a meloxicam aspirin cocrystal that exhibits enhanced solubility and pharmacokinetics. J Pharm Sci 2011;100:2172–2181.
   PubMed Web of Science ®Google Scholar
• Basavoju S, Boström D, Velaga SP. Indomethacin-saccharin cocrystal: design, synthesis and preliminary pharmaceutical characterization. Pharm Res 2008;25:530–541.
   PubMed Web of Science ®Google Scholar
• Remenar JF, Morissette SL, Peterson ML, Moulton B, MacPhee JM, Guzmán HR et al. Crystal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids. J Am Chem Soc 2003;125:8456–8457.
   PubMed Web of Science ®Google Scholar
• Shiraki K, Takata N, Takano R, Hayashi Y, Terada K. Dissolution improvement and the mechanism of the improvement from cocrystallization of poorly water-soluble compounds. Pharm Res 2008;25:2581–2592.
   PubMed Web of Science ®Google Scholar
• Tsutsumi S, Iida M, Tada N, Kojima T, Ikeda Y, Moriwaki T et al. Characterization and evaluation of miconazole salts and cocrystals for improved physicochemical properties. Int J Pharm 2011;421:230–236.
   PubMed Web of Science ®Google Scholar
• Rodrı´guez-Hornedo N, Nehm SJ, Jayasankar A. Cocrystals: design, properties and formation mechanisms. In: Swarbrick J, ed. Encyclopedia of pharmaceutical technology. New York: Informa Health Care, 2007:615–635.
   Google Scholar
• Sun CC, Hou H. Improving mechanical properties of caffeine and methyl gallate crystals by cocrystallization. Cryst Growth Des 2008;5:1575–1579.
   Google Scholar
• McNamara DP, Childs SL, Giordano J, Iarriccio A, Cassidy J, Shet MS et al. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API. Pharm Res 2006;23:1888–1897.
   PubMed Web of Science ®Google Scholar
• Jung MS, Kim JS, Kim MS, Alhalaweh A, Cho W, Hwang SJ et al. Bioavailability of indomethacin-saccharin cocrystals. J Pharm Pharmacol 2010;62:1560–1568.
   PubMed Web of Science ®Google Scholar
• Stark P, Hardison CD. A review of multicenter controlled studies of fluoxetine vs. imipramine and placebo in outpatients with major depressive disorder. J Clin Psychiatry 1985;46:53–58.
   PubMed Web of Science ®Google Scholar
• Thallypally PK, Nangia A. A Cambridge Structural Database analysis of the C–H... Cl interaction: C–H... Cl– and C–H... Cl–M often behave as hydrogen bonds but C–H... Cl–C is generally a van der Waals interaction. Cryst Eng Comm 2001;3:114.
   Google Scholar
• Variankaval N, Wenslow R, Murry J, Hartman R, Helmy R, Kwong E, Clas SD, Dalton C, Santos I. Preparation and Solid-State Characterization of Nonstoichiometric Cocrystals of a Phosphodiesterase-IV Inhibitor and L-Tartaric acid. Cryst Growth Des 2006;6:690–700.
   Web of Science ®Google Scholar
• Wenger M, Bernstein J. Designing a cocrystal of gamma-amino butyric acid. Angew Chem Int Ed Engl 2006;45:7966–7969.
   PubMed Web of Science ®Google Scholar
• Zhang GG, Henry RF, Borchardt TB, Lou X. Efficient co-crystal screening using solution-mediated phase transformation. J Pharm Sci 2007;96:990–995.
   PubMed Web of Science ®Google Scholar
• Cheney ML, Weyna DR, Shan N, Hanna M, Wojtas L, Zaworotko MJ. supramolecular architechtures of meloxicam carboxylic acid cocrystals, a Crystal Engineering Case Study. Cryst Growth Des 2010;10:4401–4413.
   Web of Science ®Google Scholar
• Lu J, Li Y, Wang J, Li Z, Rohani S, Ching C. Pharmaceutical cocrystals: a comparison of sulfamerazine with sulfamethazine. J Cryst Growth 2011;335:110–114.
   Web of Science ®Google Scholar
• United States Pharmacopeia 30, NF 25. Rockville: United States Pharmacopeial Convention 2007:2165–2170.
   Google Scholar
• Risley DS, Bopp RJ. Fluoxetine. In: Florey K. ed. Analytical profiles of drug substances. New York: Academic Press 2005;19:193–219.
   Google Scholar
• Childs SL, Stahly GP, Park A. The salt-cocrystal continuum: the influence of crystal structure on ionization state. Mol Pharm 2007;4:323–338.
   PubMed Web of Science ®Google Scholar
• Silverstein RM, Webster FX, Kiemle DJ. Spectrometric identification of organic compounds, New York: John Wiley & Sons Inc 2005:72–126.
   Google Scholar
• Heacock RN, MarionL. Infrared spectra of secondary amines and their salts. Canadian J Chem 1956;34:1782–1795.
   Web of Science ®Google Scholar
• Tiwary AK. Crystal habit changes and dosage form performance. In: Swarbrick J. ed. Encyclopedia of pharmaceutical technology. New York: Informa Health Care 2007:820–833.
   Google Scholar
• Jagannathan NR, Rao CNR. A 13C NMR spectroscopic study of the phase transitions of alkane dicarboxylic acids in the solid state. Chem Phys Lett 1987;140:46–50.
   Web of Science ®Google Scholar
• Stanton MK, Bak A. Physicochemical properties of pharmaceutical co-crystals: a case study of ten AMG 517 co-crystals. Cryst Growth Des 2008;8:3856–3862.
   Web of Science ®Google Scholar
• Higuchi T, Connors KA. Phase solubility techniques. Adv Anal Chem Instr 1965;4:117–9.
   Google Scholar
• Connors KA. Acid-base equilibria. In: Thermodynamics of pharmaceutical systems. Hoboken, NJ: John Wiley & Sons Inc. 2002:185–188.
   Google Scholar
• Reddy LS, Bethune SJ, Kampf JW, Rodriguez-Hornedo N. Cocrystals and salts of gabapentin: ph dependent cocrystal stability and solubility. Cryst Growth Des 2009;9:378–385.
   Web of Science ®Google Scholar
• The Merck Index, Fourteenth Edition. 2006. Editor – O’Neil MJ, Published by Merck Research Laboratories, Division of Merck & Co., Inc., Whitehouse Station, NJ, USA.
   Google Scholar
• Keraliya RA, Soni TG, Thakkar VT, Gandhi TR. Effect of Solvent on Crystal Habit and Dissolution behavior of Tolbutamide by Initial Solvent Screening. Dissolution Technol 2010;1:16–21.
   Google Scholar
• Chow AHL, Hsia CK, Gordon JD, Young JWM. Vargha-Buttler EI. Assessment of wettability and its relationship to the intrinsic dissolution rate of doped phenytoin crystals. Int J Pharm 1995;126:21–28.
   Web of Science ®Google Scholar