Gas anti-solvent processing of a new sulfamethoxazole-L-malic acid cocrystal

Rawin Imchalee; Manop Charoenchaitrakool

Journal of Industrial and Engineering Chemistry, Vol.25, 12-15, May, 2015

DOI10.1016/j.jiec.2014.11.009 Export Citation

Gas anti-solvent processing of a new sulfamethoxazole-L-malic acid cocrystal

Rawin Imchalee¹, and Manop Charoenchaitrakool^{1, 2, †}

¹Department of Chemical Engineering, Faculty of Engineering, Kasetsart University, Bangkok 10900, Thailand
²Center for Advanced Studies in Nanotechnology for Chemical, Food and Agricultural Industries, Kasetsart University, Bangkok 10900, Thailand

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The objective of this work was to enhance the dissolution rate of a poorly water-soluble antibiotic drug, sulfamethoxazole (SMX), by forming cocrystal with l-malic acid (MA) using gas anti-solvent (GAS) process. The effect of SMX to MA mass ratio (2:1, 1.5:1 and 1:1) on drug content and dissolution rate was investigated. The GAS cocrystallization was carried out at 45 °C using the drug concentration of 50% saturation in acetone. It was found that cocrystals produced from SMX to MA ratio of 2:1 had higher drug content than those produced from the ratios 1.5:1 and 1:1. In the dissolution studies, it was found that 90% of SMX in the cocrystals could be dissolved within 4.2 min, whereas the times required to dissolve 90% of the drug in the physical mixtures were 8.2 min (ratio 1:1) and 25 min (ratio 2:1), and up to 28 min for the micronized SMX.

Keywords:Crystallization;Co-precipitation;Cocrystal;Sulfamethoxazole;L-Malic acid

[References]

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Thakuria R, Delori A, Jones W, Lipert MP, Roy L, Rodrıguez-Hornedo N, Int. J. Pharm., 453, 101 (2013)
Padrela L, Rodrigues MA, Tiago J, Velaga SP, Matos HA, de Azevedo EG, J. Supercrit. Fluids, 86, 129 (2014)
Qiao N, Wang K, Schlindwein W, Davies A, Li M, J. Pharm. Biopharm., 83, 415 (2013)
Steed JW, Trends Pharmacol. Sci., 34, 185 (2013)
Blagden N, de Matas M, Gavan PT, York P, Adv. Drug Deliv. Rev., 59, 617 (2007)
Trask AV, Motherwell WDS, Jones W, Int. J. Pharm., 320, 114 (2006)
Maeno Y, Fukami T, Kawahata, Yamaguchi K, Tagami T, Ozeki T, Suzuki T, Tomono K, Int. J. Pharm., 473, 179 (2014)
Basvoju S, Bostrom D, Velaga SP, Pharm. Res., 25, 530 (2008)
Shan N, Zaworotko MJ, Drug Discov. Today, 13, 440 (2008)
Qiao N, Li M, Schlindwein W, Malek N, Davies A, Trappitt G, Int. J. Pharm., 419, 1 (2011)
Najar AA, Azim Y, J. Indian Inst. Sci., 94, 45 (2014)
Tsutsumi S, Iida M, Tada N, Kojima T, Ikeda Y, Moriwaki T, Higashi K, Moribe K, Yamamoto K, Int. J. Pharm., 421, 230 (2011)
Shiraki K, Takata N, Takano R, Hayashi Y, Terada K, Pharm. Res., 25, 2581 (2008)
Ober CA, Montgomery SE, Gupta RB, Powder Technol., 236, 122 (2013)
Ober CA, Gupta RB, AAPS Pharm. Sci. Technol., 13, 1396 (2012)
Shayanfar A, Asadpour-Zeynali K, Jouyban A, J. Mol. Liq., 187, 171 (2013)
Neurohr C, Revelli AL, Billot P, Marchivie M, Lecomte S, Laugier S, Massip S, Subra-Patemault P, J. Supercrit. Fluids, 83, 78 (2013)
Chang YP, Tang M, Chen YP, J. Mater. Sci., 43(7), 2328 (2008)
Phothipanyakun S, Suttikornchai S, Charoenchaitrakool M, Powder Technol., 250, 84 (2013)
Imchalee R, Production of cocrystal between sulfamethoxazole drug and L-malicacid using gas anti-solvent (GAS) process, (M.Eng. thesis), Kasetsart University, Thailand, 2014.

[Referenced By]

[1] Hiendrawan S, Veriansyah B, Tjandrawinata RR, J. Ind. Eng. Chem., 20(1), 54 (2014)

[2] Thakuria R, Delori A, Jones W, Lipert MP, Roy L, Rodrıguez-Hornedo N, Int. J. Pharm., 453, 101 (2013)

[3] Padrela L, Rodrigues MA, Tiago J, Velaga SP, Matos HA, de Azevedo EG, J. Supercrit. Fluids, 86, 129 (2014)

[4] Qiao N, Wang K, Schlindwein W, Davies A, Li M, J. Pharm. Biopharm., 83, 415 (2013)

[5] Steed JW, Trends Pharmacol. Sci., 34, 185 (2013)

[6] Blagden N, de Matas M, Gavan PT, York P, Adv. Drug Deliv. Rev., 59, 617 (2007)

[7] Trask AV, Motherwell WDS, Jones W, Int. J. Pharm., 320, 114 (2006)

[8] Maeno Y, Fukami T, Kawahata, Yamaguchi K, Tagami T, Ozeki T, Suzuki T, Tomono K, Int. J. Pharm., 473, 179 (2014)

[9] Basvoju S, Bostrom D, Velaga SP, Pharm. Res., 25, 530 (2008)

[10] Shan N, Zaworotko MJ, Drug Discov. Today, 13, 440 (2008)

[11] Qiao N, Li M, Schlindwein W, Malek N, Davies A, Trappitt G, Int. J. Pharm., 419, 1 (2011)

[12] Najar AA, Azim Y, J. Indian Inst. Sci., 94, 45 (2014)

[13] Tsutsumi S, Iida M, Tada N, Kojima T, Ikeda Y, Moriwaki T, Higashi K, Moribe K, Yamamoto K, Int. J. Pharm., 421, 230 (2011)

[14] Shiraki K, Takata N, Takano R, Hayashi Y, Terada K, Pharm. Res., 25, 2581 (2008)

[15] Ober CA, Montgomery SE, Gupta RB, Powder Technol., 236, 122 (2013)

[16] Ober CA, Gupta RB, AAPS Pharm. Sci. Technol., 13, 1396 (2012)

[17] Shayanfar A, Asadpour-Zeynali K, Jouyban A, J. Mol. Liq., 187, 171 (2013)

[18] Neurohr C, Revelli AL, Billot P, Marchivie M, Lecomte S, Laugier S, Massip S, Subra-Patemault P, J. Supercrit. Fluids, 83, 78 (2013)

[19] Chang YP, Tang M, Chen YP, J. Mater. Sci., 43(7), 2328 (2008)

[20] Phothipanyakun S, Suttikornchai S, Charoenchaitrakool M, Powder Technol., 250, 84 (2013)

[21] Imchalee R, Production of cocrystal between sulfamethoxazole drug and L-malicacid using gas anti-solvent (GAS) process, (M.Eng. thesis), Kasetsart University, Thailand, 2014.