Korean Journal of Chemical Engineering, Vol.35, No.9, 1860-1866, September, 2018
Growth retardation of diflunisal in antisolvent crystallization
Diflunisal, an analgesic anti-inflammatory drug, was recrystallized from acetone solution using water and carbon dioxide as antisolvents. The crystallized diflunisal showed an acicular crystal habit with a very high aspect ratio. Growth retardation of diflunisal crystals was observed when ultrasound was added during the recrystallization and when habit-modifying agents were applied to the system. For example, an increase in sebacic acid concentration from 0.229 to 2.132 wt% lowered the aspect ratio of the crystal from 62 to 8.5, while an increase in Span 83 concentration from 1.712 to 4.415 wt% reduced the aspect ratio from 11 to 4.0. Differential scanning calorimetry and X-ray diffraction analysis revealed that the presence of ultrasound and habit-modifying agents may induce structural modifications as well as the growth retardation of diflunisal crystals.
- Prosapio V, Reverchon E, De Marco I, J. Supercrit. Fluids, 107, 106 (2016)
- Cuadra IA, Cananas A, Cheda JAR, Martinez-Casado FJ, Pando C, J. CO2 Utiliz., 13, 29 (2016)
- Neurohr C, Marchivie M, Lecomte S, Cartigny Y, Couvrat N, Sanselme M, Subra-Paternault P, Cryst. Growth Des., 15, 4616 (2015)
- Kaialy W, Larhrib H, Chikwanha B, Shojaee S, Nokhodchi A, Int. J. Pharm., 464, 53 (2014)
- Park SJ, Yeo SD, J. Supercrit. Fluids, 47(1), 85 (2008)
- Myerson AS, Handbook of Industrial Crystallization, 2nd Ed., Chapter 3, Butterworth Heinemann, Boston (2002).
- Van Rosmalen GM, J. Cryst. Growth, 99, 1053 (1990)
- Thompson C, Davies MC, Roberts CJ, Tendler SJB, Wilkinson MJ, Int. J. Pharm., 280, 137 (2004)
- Cotton ML, Hux RA, Analyt. Profil. Drug Subst., 14, 491 (1985)
- Giammona G, Cavallaro G, Pitarresi G, Ventura C, Palazzo S, Int. J. Pharm., 105, 57 (1994)
- Martinez-Oharriz MC, Martin C, Goni MM, Rodriguez-Espinosa C, De Ilarduya-Apaolaza MCT, Sanchez M, J. Pharm. Sci., 83, 174 (1994)
- Ford JL, Timmins P, Pharmaceutical Thermal Analysis, Ellis-Horwook Ltd., Chichester, U.K. (1989).