Agomelatine co-crystals with resorcinol and hydroquinone: Preparation and characterization

Min-Jeong Lee; Nan-Hee Chun; Hyo-Cheol Kim; Moon-Jip Kim; Paul Kim; Min-Yong Cho; Guang Jin Choi

Korean Journal of Chemical Engineering, Vol.35, No.4, 984-993, April, 2018

DOI10.1007/s11814-017-0331-7 Export Citation

Agomelatine co-crystals with resorcinol and hydroquinone: Preparation and characterization

Min-Jeong Lee¹, Nan-Hee Chun², Hyo-Cheol Kim³, Moon-Jip Kim³, Paul Kim⁴, Min-Yong Cho⁴, and Guang Jin Choi^{4, 5, †}

¹Crystallization and Particle Science, Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1 Pesek Road, Jurong Island 627833, Singapore
²Unimed Pharm Inc., Asan, Chungnam 31501, Korea
³Department of Physics, Soonchunhyang University, Asan, Chungnam 31538, Korea
⁴Department of Pharmaceutical Engineering, Soonchunhyang University, Asan, Chungnam 31538, Korea
⁵Department of Medical Science, Soonchunhyang University, Asan, Chungnam 31538, Korea

E-mail:

Perovskite type BiFeO3 (BFO) was synthesized by sol-gel auto-combustion method. Synthesized BFO was immobilized on the micro slides glass plates by sol-gel dip-coating method. The sample was characterized by XRD, FESEM, UV-Vis DRS, and BET techniques. The XRD pattern confirmed the perovskite structure, and from the Debye- Scherrer equation the average crystalline size was calculated as 19 nm. The FE-SEM images of prepared BFO showed porous structure with low agglomeration. The band gap energy was calculated about 2.13 eV, and the specific surface area (SSA) of prepared BFO nanostructure was obtained 55.1m2 g-1. The photocatalytic activity of prepared pure and immobilized BFO was investigated in the removal of NOx under UV irradiation, in the batch photoreactor. The effects of operational parameters such as initial concentration of NOx, light intensity and amount of coated photocatalyst, under identical conditions, were investigated. The results showed that the highest conversion of NOx was obtained as 35.83% in the 5 ppm of NOx with 1.2 g immobilized BFO and under 15 W illumination lamp.

Keywords:Co-crystal;Agomelatine;Resorcinol;Hydroquinone;Solubility

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[Referenced By]

[1] Prohens R, Barbas R, Portell A, Font-Bardia M, Alcobe X, Puigjaner C, Cryst. Growth Des., 16, 1063 (2016)

[2] Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ, J. Pharm. Sci., 95, 499 (2006)

[3] Babu NJ, Nangia A, Cryst. Growth Des., 11, 2662 (2011)

[4] Aitipamula S, Banerjee R, Bansal AK, Biradha K, Cheney ML, Choudhury AR, Desiraju GR, Dikundwar AG, Dubey R, et al., Cryst. Growth Des., 12, 2147 (2012)

[5] US FDA, Guidance for Industry: Regulatory Classification of Pharmaceutical Co-crystals; http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/UCM516813.pdf (2016).

[6] US FDA, Guidance for Industry: Regulatory Classification of Pharmaceutical Co-crystals, http://www.fda.gov/downloads/Drugs/ GuidanceComplianceRegulatoryInformation/Guidances/UCM281764.pdf (2013).

[7] US FDA. Generally Regarded as Safe, http://www.fda.gov/Food/IngredientsPackagingLabeling/GRAS/.

[8] US FDA. Everything Added to Food Stuff in the United States, http://www.fda.gov/Food/ IngredientsPackagingLabeling/FoodAdditivesIngredients/ucm115326.htm, http://www.accessdata.fda.gov/scripts/fcn/fcnnavigation.cfm?rpt=eafuslisting.

[9] Remenar JF, Peterson ML, Stephens PW, Zhang Z, Zimenkov Y, Hickey MB, Mol. Pharm., 4, 386 (2007)

[10] Bak A, Gore A, Yanez E, Stanton M, Tufekcic S, Syed R, Akrami A, Rose M, Surapaneni S, Bostick T, King A, Neervannan S, Ostovic D, Koparkar A, J. Pharm. Sci., 97, 3942 (2008)

[11] Hickey MB, Peterson ML, Scoppettuolo LA, Morrisette SL, Vetter A, Guzman H, Remenar JF, Zhang Z, Tawa MD, Haley S, Zaworotko MJ, Almarsson O, Eur. J. Pharm. Biopharm., 67, 112 (2007)

[12] Schultheiss N, Newman A, Cryst. Growth Des., 9, 2950 (2009)

[13] Lee MJ, Wang IC, Kim MJ, Kim P, Song KH, Chun NH, Park HG, Choi GJ, Korean J. Chem. Eng., 32(9), 1910 (2015)

[14] Demyttenaere K, Eur. Neuropsychopharmacol., 21, A703 (2011)

[15] de Bodinat C, Guardiola-Lemaitre B, Mocaer E, Renard P, Munoz C, Millan MJ, Nat. Rev. Drug Discov., 9, 628 (2010)

[16] VALDOXAN® - Product Information. http://www.guildlink.com.au/gc/ws/servier/pi.cfm?product= sepvaldx.

[17] Zheng SL, Chen JM, Zhang WX, Lu TB, Cryst. Growth Des., 11, 466 (2011)

[18] Zhang Q, Jiang L, Mei X, Pharm. Dev. Technol., 21, 196 (2016)

[19] Yan Y, Chen JM, Geng N, Lu TB, Cryst. Growth Des., 12, 2226 (2012)

[20] Yin HS, Zhang QM, Zhou YL, Ma QA, Liu T, Zhu LS, Ai SY, Electrochim. Acta, 56(6), 2748 (2011)

[21] Cherukuvada S, Nangia A, Chem. Commun., 50, 906 (2014)

[22] Tata J, Scalarone D, Lazzari M, Chiantore O, Eur. Polym. J., 45, 2520 (2009)

[23] Lu E, Rodriguez-Hornedo N, Suryanarayanan R, CrystEngComm., 10, 665 (2008)

[24] Yamashita H, Hirakura Y, Yuda M, Teramura T, Terada K, Pharm. Res., 30, 70 (2013)

[25] Yamashita H, Hirakura Y, Yuda M, Terada K, Pharm. Res., 31, 1946 (2014)

[26] Zhou Z, Chan HM, Sung HHY, Tong HHY, Zheng Y, Pharm. Res., 33, 1030 (2016)

[27] Friscic T, Jones W, Cryst. Growth Des., 9, 1621 (2009)

[28] Chadwick K, Davey R, Cross W, CrystEngComm., 9, 732 (2007)

[29] Tamura R, Miyata M, Advances in organic crystal chemistry: Comprehensive reviews, Springer Japan, Tokyo (2015).

[30] Kaur R, Row TNG, Cryst. Growth Des., 12, 2744 (2012)

[31] Kaur R, Cherukuvada S, Managutti PB, Row TNG, CrystEngComm., 18, 3191 (2016)

[32] Alhalaweh A, George S, Basavoju A, Childs SL, Rizvic SAA, Velaga SP, CrystEngComm., 14, 5078 (2012)

[33] Elbagerma MA, Edwards HGM, Munshi T, Scowen IJ, CrystEngComm., 13, 1877 (2011)

[34] Mayo DW, Miller FA, Hannah RW, Course notes on the interpretation of infrared and Raman spectra, Wiley, New Jersey (2004).

[35] Socrates G. Infrared and Raman characteristic group frequencies: Tables and charts, 3rd Ed., Wiley, New York (2001).

[36] Good DJ, Rodriguez-Hornedo N, Cryst. Growth Des., 9, 2252 (2009)

[37] DrugBank - Agomelatine, https://www.drugbank.ca/drugs/DB06594.

[38] Du W, Zhou Y, Gong Y, Zhao C, Asian J. Pharm. Sci., 8, 181 (2013)

[39] Saha R, Sengupta S, Dey SK, Steele IM, Bhattacharyya A, Biswas S, Kumar S, RSC Adv., 4, 49070 (2014)