Co-Amorphous Telmisartan-Pimelic Acid with Improved Solubility

Abstract:

Telmisartan (TEL), a type of antihypertensive drug, has poor solubility. To improve its solubility, the co-amorphous telmisartan with pimelic acid (PA) in molar ratio of 1:1 and 2:1, respectively, were obtained using a liquid-assisted grinding method. The co-amorphous system was characterized by the powder X-ray diffraction and differential scanning calorimetry. The molecular interactions of the co-amorphous were studied by the infrared spectra. After the formation of co-amorphous, the solubility of TELwas much improved, and the apparent solubility values were approximately 9-15 times as high as that of crystalline TEL. Moreover, the co-amorphous TEL-PA was stored under 25 °C/20% RH for a month without any evidence of conversion by powder X-ray diffraction analysis.

• Periodical: Materials Science Forum (Volume 993)
• Pages: 776-784
• DOI: https://doi.org/10.4028/www.scientific.net/MSF.993.776
• Online since: May 2020
• Authors: Ze Xin Wu, Wen Zhe Ma, Lei Wang*, Chang Lin Yao, Shuang Song, Xin Yuan Wang
• Keywords: Co-Amorphous, Liquid-Assisted Grinding Method, Solubility

References

[1] Jia-Mei, Chen, Tong-Bu, Lu. Improving the Solubility of Agomelatine via Cocrystals. Cryst. Growth Des: 2012. 2226-2233.

[2] Yoshinari, Y.; Forbes, R. T.; York, P.; Kawashima, Chemical characterisation of sodium starch glycolate particles,Y. Int. J. Pharm. 2002, 247, 69ium.

[3] Almarsson, ö.; Zaworotko, Crystal engineering of the composition of pharmaceutical phases. Dopharmaceutical co-crystals represent a new path to improved medicines, Chem. Commun. 2004, 1889, 1889.

DOI: 10.1039/b402150a

[4] Shuai Qian, Yuan, Gao, Jianjun, Zhang, Yuanfeng, Wei, Weili, Heng. Coamorphous Lurasidone Hydrochloride−Saccharin with Charge- Assisted Hydrogen Bonding Interaction Shows Improved Physical Stability and Enhanced Dissolution with pH-Independent Solubility Behavior. Cryst. Growth Des: 2015. 2920-2928.

DOI: 10.1021/acs.cgd.5b00349

[5] Kawakami K, Ida Y. Direct observation of the enthalpy relaxation and the recovery processes of maltose-based amorphous formulation by isothermal microcalorimetry. Pharm Res. 2003, 20(9):1430–6.

[6] Yoshioka M, Hancock B, Zografi G. Crystallization of indomethacin from amorphous state below and above its glass transition temperature, J Pharm Sci. 1994, 83(12): 1700700.

DOI: 10.1002/jps.2600831211

[7] a. Aljohani, Marwah, McArdle, Patrick, Erxleben, Andrea., Investigate the formation of drug-drug cocrystals and coamorphous systems of the antidiabetic drug gliclazide. Int. J. Pharm., 2019, 561, 35-42. b. Knapik-Kowalczuk, Justyna., Wenkang, Tu., Chmiel, Krzysztof., Costabilization of amorphous pharmaceuticals- the case of nifedipine and nimodipine, Mol. Pharmaceutics, 2018, 1, 2455-2465. c. Kissi, Eric Ofosu, Kasten, Georgia, Lobmann, Korbinian, The role of glass transition temperatures in coamorphous drug-amino acid formulations, Mol. Pharmaceutics, 2018, 1. 4247-4256.

DOI: 10.1021/acs.molpharmaceut.8b00650

[8] Riikka Laitinen, Thomas, Rades, Holger, Grohganz, Keith, C, Gordon, Clare, Strachan. Coamorphous Drug Systems: Enhanced Physical Stability and Dissolution Rate of Indomethacin and Naproxen. Mol. Pharmaceutics: 2011, 1919-1928.

DOI: 10.1021/mp2002973

[9] Kuthuru Suresh, M, K, Chaitanya, Mannava, Ashwini, Nangia. A novel curcumin–artemisinin coamorphous solid: physical properties and pharmacokinetic profile. RSC Adv: 2014, 58357-58361.

DOI: 10.1039/c4ra11935e

[10] Shuai Qian, Weili, Heng, Yuanfeng, Wei, Jianjun, Zhang, Yuan, Gao. Coamorphous Lurasidone Hydrochloride−Saccharin with Charge- Assisted Hydrogen Bonding Interaction Shows Improved Physical Stability and Enhanced Dissolution with pH-Independent Solubility Behavior. Cryst. Growth Des: 2015, 2920-2928.

DOI: 10.1021/acs.cgd.5b00349

[11] Dinnebier, William, I, F, David, Kenneth, Shankland, Herbert, NarR, Peter, Sieger. Structural Characterization of Three Crystalline Modifications of Telmisartan by Single Crystal and High-Resolution X-ray Powder Diffraction. Robert E. 2000, 1465-1479.

DOI: 10.1002/1520-6017(200011)89:11<1465::aid-jps9>3.0.co;2-c

[12] Korbinian L€obmann, Riikka, Laitinen, Holger, Grohganz, Keith, C, Gordon, Clare, Strachan, Thomas, Rades. Coamorphous Drug Systems: Enhanced Physical Stability and Dissolution Rate of Indomethacin and Naproxen. Mol. Pharmaceutics: 2011, 1919-1928.

DOI: 10.1021/mp2002973

[13] Heinz, A.; Gordon, K. C.; McGoverin, C. M.; Rades, T.; Strachan, C. J. Understanding the solid-state forms of fenofibrate - A spectroscopic and computational study. Eur. J. Pharm. Biopharm. 2009, 71 (1), 100-108.

DOI: 10.1016/j.ejpb.2008.05.030

[14] Allesø, M., Chieng, N., Rehder, S., Rantanen, J., Rades, T., Aaltonen, J., 2009. Enhanced dissolution rate and synchronized release of drugs in binary systems through formulation: amorphous naproxen–cimetidine mixtures prepared by mechanical activation. J. Controlled Release 136, 45-53.

DOI: 10.1016/j.jconrel.2009.01.027

[15] Yan Yan, Tong-Bu, Lu. Simultaneously enhancing the solubility and permeability of acyclovir by crystal engineering approach. CrystEngComm: 2013, 6457-6460.

DOI: 10.1039/c3ce41017j

[16] Tong-Bu, Lu. Lenalidomide−Gallic Acid Cocrystals with Constant High Solubility[M]. Cryst. Growth Des:Jia-Xi Song, 2015, 4869-4875.

DOI: 10.1021/acs.cgd.5b00699

[17] Tong-Bu, Lu. Improving the Solubility of Lenalidomide via Cocrystals[M]. Cryst. Growth Des:Jia-Xi Song, 2014, 3069-3077.

[18] Juan, R, Sanchez-Ramos, Shijie, Song, Michael, J, Zaworotko. Effects of Crystal Form on Solubility and Pharmacokinetics: A Crystal Engineering Case Study of Lamotrigine[M]. Cryst. Growth Des.: Miranda L, 2010, 394-405.

DOI: 10.1021/cg901010v

[19] Yong Chen, Jia-Mei, Chen, Tong-Bu, Lu, Yu-Yu, Ma. Improving the Solubility and Bioavailability of Apixaban via Apixaban−Oxalic Acid Cocrystal[M]. Cryst. Growth Des.: 2016. 2923-2930.

DOI: 10.1021/acs.cgd.6b00266

[20] Sanjay, Mandal, Sadhika, Khullar, Jamshed, Haneef, Swati, Bhandari. Cocrystals of telmisartan: characterization, structure elucidation, in vivo and toxicity studies . CrystEngComm: Renu Chadha, 2014. 8375-8389.

DOI: 10.1039/c4ce00797b