Formation of Ketoprofen-Malonic Acid Cocrystal by Solvent Evaporation Method

Yudi Wicaksono; Dwi Setyawan; Siswandono Siswandono

doi:10.22146/ijc.24884

Formation of Ketoprofen-Malonic Acid Cocrystal by Solvent Evaporation Method

https://doi.org/10.22146/ijc.24884

Yudi Wicaksono^(1*), Dwi Setyawan⁽²⁾, Siswandono Siswandono⁽³⁾

(1) Faculty of Pharmacy, University of Jember Center for Development of Advanced Science and Technology, University of Jember
(2) Faculty of Pharmacy, Airlangga University
(3) Faculty of Pharmacy, Airlangga University
(*) Corresponding Author

Abstract

The purpose of this work was to explore the formation of ketoprofen-malonic acid cocrystal by solvent evaporation method. Early detection of cocrystal formation was conducted by hot stage microscopy and solid-liquid phase diagram. Cocrystal were prepared by solvent evaporation method by using isopropyl alcohol as solvent. Characterization of cocrystal was done by Powder X-Ray Diffractometry (PXRD), Differential Scanning Calorimetry (DSC), Fourier Transform Infrared (FTIR) Spectroscopy and Scanning Electron Microscopy (SEM). The results of hot stage microscopic and solid-liquid phase diagram indicated formation of ketoprofen-malonic acid cocrystal. PXRD and DSC measurements showed stoichiometric ratio of cocrystal ketoprofen-malonic acid (2:1). The ketoprofen-malonic acid cocrystal had melting point at 86.2 °C and unique peaks of PXRD pattern at 2θ of 6.1°, 17.8°, 23.2° and 28.6°. FTIR spectra indicated the formation of cocrystal due to interaction of C=O ketone group of ketoprofen with MA molecule. SEM images show that ketoprofen-malonic acid cocrystal have multi-shaped particles with rough surfaces.

Keywords

ketoprofen; cocrystal; hot stage microscopy; solid-liquid phase diagram

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References

[1] Khaleel, N.Y., Abdulrasool, A.A., Ghareeb, M.M., and Hussain, S.A., 2011, Solubility and dissolution improvement of ketoprofen by solid dispersion in polymer and surfactant using solvent evaporation method, Int. J. Pharm. Pharm. Sci., 3 (4), 431–435.

[2] Vaghela, R., Kulkarni, P.K., Hani, U., Varma, V.N.S.K., and Abhay, R., 2014, Enhancing aqueous solubility of ketoprofen by fusion technique using suitable co-formers, Curr. Drug Ther., 9, 199–207.

[3] Rençber, S., Karavana, S.Y., and Özyazici, M., 2009, Bioavailability file: Ketoprofen, Fabad J. Pharm. Sci., 34, 203–216.

[4] Padrela, L., Rodrigues, M.A., Velaga, S.P., Matos, H.A., and de Azevedo, E.G., 2009, Formation of indomethacin–saccharin cocrystals using supercritical fluid technology, Eur. J. Pharm. Sci., 38 (1), 9–17.

[5] Mashhadi, S.M.A., Yunus, U., Bhatti, M.H., and Tahir, M.N., 2014, Isoniazid cocrystals with anti-oxidant hydroxy benzoic acids, J. Mol. Struct., 1076, 446–452.

[6] Thakuria, R., Delori, A., Jones, W., Lipert, M.P., Roy, L., and Rodríguez-Hornedo, N., 2013, Pharmaceutical cocrystals and poorly soluble drugs, Int. J. Pharm., 453 (1), 101–125.

[7] Qiao, N., Li, M., Schlindwein, W., Malek, N., Davies, A., and Trappitt, G., 2011, Pharmaceutical cocrystals: An overview, Int. J. Pharm., 419 (1-2), 1–11.

[8] Maeno, Y., Fukami, T., Kawahata, M., Yamaguchi, K., Tagami, T., Ozeki, T., Suzuki, T., and Tomono, K., 2014, Novel pharmaceutical cocrystal consisting of paracetamol and trimethylglycine, a new promising cocrystal former, Int. J. Pharm., 473 (1-2), 179–186.

[9] Desale, P.K., 2013, A novel method: Co-crystallisation, Int. J. Pharm. Invent., 3 (1), 19–26.

[10] Setyawan, D., Sari, R., Yusuf, H., and Primaharinastiti, R., 2014, Preparation and characterization of artesunate-nicotinamide cocrystal by solvent evaporation and slurry method, Asian J. Pharm. Clin. Res., 7 (Suppl 1), 62–65.

[11] Klímová, K., and Leitner J., 2012, DSC study and phase diagrams calculation of binary systems of paracetamol, Thermochim. Acta, 550, 59–64.

[12] Berry, D.J., Seaton, C.C., Clegg, W., Harrington, R.W., Coles, S.J., Horton, P.N., Hursthouse, M.B., Storey, R., Jones, W., Friscic, T., and Blagden, N., 2008, Applying hot-stage microscopy to co-crystal screening: A study of nicotinamide with seven active pharmaceutical ingredients, Cryst. Growth Des., 8 (5), 1697–1712.

[13] Pal, S., Roopa, B.N., Abu, K., Manjunath, S.G., and Nambiar, S., 2014, Thermal studies of furosemide–caffeine binary system that forms a cocrystal, J. Therm. Anal. Calorim, 115 (3), 2261-2268.

[14] Manin, A.N., Voronin, A.P., Drozd, K.V., Manin, N.G., Bauer-Brandl, A., and Perlovich, G.L., 2014, Cocrystal screening of hydroxybenzamides with benzoic acid derivatives: A comparative study of thermal and solution-based methods, Eur. J. Pharm. Sci., 65, 56–64.

[15] Giron, D., 2007, Encyclopedia of Pharmaceutical Technology, Informa Healthcare USA, Inc., New York, 3726–3729.

[16] Tiţa, B., Fuliaş, A., Bandur, G., Marian, E., and Tiţa, D., 2011, Compatibility study between ketoprofen and pharmaceutical excipients used in solid dosage forms, J. Pharm. Biomed. Anal., 56 (2), 221–227.

[17] Limwikrant, W., Nagai, A., Hagiwara, Y., Higashi, K., Yamamoto, K., and Moribe, K., 2012, Formation mechanism of a new carbamazepine/malonic acid cocrystal polymorph, Int. J. Pharm., 431 (1-2), 237–240.

[18] Meltzer, V., and Pincu, E., 2012, Thermodynamic study of binary mixture of citric acid and tartaric acid, Cent. Eur. J. Chem., 10 (5), 1584–1589.

[19] Patel, J.R., Carlton, R.A., Needham, T.E., Chichester, C.O., and Vogt, F.G., 2012, Preparation, structural analysis, and properties of tenoxicam cocrystals, Int. J. Pharm., 436 (1-2), 685–706.

[20] Niazi, S.K., 2007, Handbook of Preformulation: Chemical, Biological, and Botanical Drugs, Informa Healthcare USA, Inc., New York, 69–75.

[21] Aakeröy, C.B., Fasulo, M.E., and Desper J., 2007, Cocrystal or salt: Does it really matter?, Mol. Pharmaceutics, 4 (3), 317–322.

[22] Blasi, P., Schoubben, A., Giovagnoli, S., Perioli, L., Ricci, M., and Rossi, C., 2007, Ketoprofen poly(lactide-co-glycolide) physical interaction, AAPS PharmSciTech., 8 (2), E78–E85.

[23] Guo, C., Zhang, H., Wang, X., Xu, J., Liu, Y., Liu, X., Huang, H., and Sun, J., 2013, Crystal structure and explosive performance of a new CL-20/caprolactam cocrystal, J. Mol. Struct., 1048, 267–273.

[24] Padrela, L., Rodrigues, M.A., Tiago, J., Velaga, S.P., Matos, H.A., and de Azevedo, E.G., 2014, Tuning physicochemical properties of theophylline by cocrystallization using the supercritical fluid enhanced atomization technique, J. Supercrit. Fluids, 86, 129–136.

DOI: https://doi.org/10.22146/ijc.24884