Thermal analysis assisted by spectra-structure studies of BCS class II active pharmaceutical ingredients: ezetimibe and lercanidipine hydrochloride. The concept of preformulation
Tóm tắt
A detailed thermal analysis investigation of title BCS class II active pharmaceutical ingredients with low solubility and high permeability and known polymorphism were reported. Differential scanning calorimetry (DSC) and thermogravimetry analysis (TG) were used as primary screening techniques to assess into the polymorphic stability of the studied APIs relative to their thermal properties. The solid-state behavior of the drug compounds was further evaluated by X-ray powder diffraction (XRPD) and Fourier transform infrared spectroscopy (FT-IR). The spectra-structural techniques were applied as supportive tools to confirm and correlate the DSC and TG results obtained by preformulation testing. As an attempt to broaden the thermal analysis, a temperature-modulated DSC (TMDSC) was developed to examine the physical properties and explain the polymorphic stability of the studied amorphous lercanidipine HCl. The TMDSC results also aimed to determine the thermal properties comprising glass transition temperature (Tg) and heat capacity (ΔCp). Based on the thermal evolution and the applied preformulation tests, both drug substances manifested considerable increase in their moisture content (hygroscopicity) in relatively short time after exposure on elevated relative humidity in stability testing chambers. The results obtained from the above-mentioned instrumentation inevitably confirmed occurrence of polymorphic transition for both active substances after recrystallization from absolute ethanol. To the best of our knowledge, the study reports new type of crystalline form of lercanidipine HCl as well as unveils the transition of anhydrous ezetimibe to monohydrate form. In addition, the thermal behavior of amorphous lercanidipine HCl is, for the first time, outlined and described in this work.
Tài liệu tham khảo
Shantikumar S, Sreekanth G, SurendraNath KV, Jafer Valli S, Satheeshkumar N. Compatibility study between Sitagliptin and pharmaceutical excipients used in solid dosage forms. J Therm Anal Cal. 2014;115:2423–8.
Maswadeh MH. Incompatibility study of ibuprofen in ternary interactive mixture by using differential scanning calorimetry. J Therm Anal Cal. 2015;123:1963–71.
International Conference on Harmonization (ICH), Guideline specification Q6A, October 1999.
Giron D, Mutz M, Garnier S. Solid state of pharmaceutical compounds Impact of the ICH Q6 guideline on industrial development. J Therm Anal Cal. 2004;77:709–47.
Murdande SB, Pikal MJ, Shanker RM, Bogner RH. Aqueous solubility of crystalline and amorphous drugs: challenges in measurement. Pharm Dev Technol. 2011;16:187–200.
Censi R, Martino DP. Polymorph impact on the bioavailability and stability of poorly soluble drugs. Molecules. 2015;20:18759–76.
Zhang GG, Law D, Schmitt EA, Qiu Y. Phase transformation considerations during process development and manufacture of solid oral dosage forms. Adv Drug Deliv Rev. 2004;56:371–90.
Zimmermann B, Baranović G. Application of differential scanning calorimetry (DSC) and modulated differential scanning calorimetry (MDSC) in food and drug industries. Polymers. 2020;12:1–21.
Thomas L, Aubuchon S. Heat capacity measurements using quasi-isothermal MDSCTM. TA Instrum Tech Notes. 1999;230:1–4.
Zimmermann B, Baranović G. Thermal analysis of paracetamol polymorphs by FT-IR spectroscopies. J Pharm Biomed Anal. 2011;54:295–302.
Fernandes PR, Nascimento do Soares CLA, Carvalho SCA, Teixeira AJ, Ionashiro M, Caires JF. Mechanochemical synthesis, characterization, and thermal behavior of meloxicam cocrystals with salicylic acid, fumaric acid, and malic acid. J Therm Anal Cal. 2019;138:765–77.
Dangelo A, Edgar B, Hurt PA, Antonijević DM. Physico-chemical characterization of three-component co-amorphous systems generated by a melt-quench method. J Therm Anal Cal. 2018;134:381–90.
Zhou D, Zhang GGZ, Law D, Grant WJD, Schmitt AE. Physical stability of amorphous pharmaceuticals: importance of configurational thermodynamic quantities and molecular mobility. J Pharm Sci. 2002;91:1863–72.
Hair PI, Scott LJ, Perry CM. Fixed-dose combination lercanidipine/enalapril. Drugs. 2007;67:95–106.
Bonifacia F. inventor, Crystal form of lercanidipine hydrochloride for use as an antihypertensive agent EP 1 600 441 B1, December 30 (2009).
Sawant M S L, Biswas M M, Khan M , Shinha S. inventors Polymorphic form of lercanidipine hydrochloride and process for preparation thereof EP 1 940 790 B1 September 2 (2015).
Heek van M, Davis H. Pharmacology of Ezetimibe Suppl. 4 (Supplement 10) Eur. Heart J. 2002 J5.
Judith A R, Tamas K N, Guy Samburski G H, Ori Lerman G, Renven I M B. Ezetimibe polymorphs US 2006/0160785 A1 July 20 2006.
Sugandha K, Kaity S, Mukherjee S, Isaac J, Ghosh A. Solubility enhancement of ezetimibe by a cocrystal engineering technique. Cryst Growth Des. 2014;14:4475–86.
Cristea M, Baul B, Ledeti I, Ledeti A, Vlase G, Vlase T, Karolewicz B, Stefanescu O, Dragomirescu OA, Muresan C, Cipu SD, Velimirovici D, Stefanescu M. Preformulation studies of atorvastatin calcium, An instrumental approach. J Therm Anal Cal. 2019;138:2799–806.
Shimpi MR, Childs SL, Bostrom D, Velaga SP. New co-crystals of ezetimibe with L-prolyne and imidazole. Cryst Eng Commun. 2014;16:8984–93.
Farias MAS, Soares FLF, Carneiro RL. Crystalline phase transition of ezetimibe in final product, after packing, promoted by the humidity of excipients: monitoring and quantification by Raman spectroscopy. J Pharm Bio Anal. 2016;121:209–14.
Bandyopadhyay R, Selbo J, Amidon GE, Hawley M. Application of powder x-ray diffraction in studying the compaction behavior of bulk pharmaceutical powders. J Pharm Sci. 2005;94:2520–30.