RESEARCH ARTICLE

Theoretical insights into influence of additives on sulfamethoxazole crystal growth kinetics and mechanisms

  • Qiao Chen ,
  • Mingdong Zhang ,
  • Yuanhui Ji
Expand
  • Jiangsu Province Hi-Tech Key Laboratory for Biomedical Research, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China
yuanhui.ji@seu.edu.cn

Received date: 30 Sep 2022

Accepted date: 15 Dec 2022

Published date: 15 Oct 2023

Copyright

2023 Higher Education Press

Abstract

In this work, the influence of the initial chemical potential gradient, stirring speed, and polymer type on sulfamethoxazole (SMX) crystal growth kinetics was systematically investigated through density functional theory (DFT) calculations, experimental measurements and the two-step chemical potential gradient model. To investigate the influence of different conditions on the thermodynamic driving force of SMX crystal growth, SMX solubilities in different polymer solutions were studied. Four model polymers effectively improved SMX solubility. It was further found that polyvinylpyrrolidone (PVP) and hydroxypropyl methyl cellulose (HPMC) played a crucial role in inhibiting SMX crystal growth. However, polyethylene glycol (PEG) promoted SMX crystal growth. The effect of the polymer on the crystal growth mechanisms of SMX was further analyzed by the two-step chemical potential gradient model. In the system containing PEG 6000, crystal growth is dominated by the surface reaction. However, in the system containing PEG 20000, crystal growth is dominated by both the surface reaction and diffusion. In addition, DFT calculations results showed that HPMC and PVP could form strong and stable binding energies with SMX, indicating that PVP and HPMC had the potential ability to inhibit SMX crystal growth.

Cite this article

Qiao Chen , Mingdong Zhang , Yuanhui Ji . Theoretical insights into influence of additives on sulfamethoxazole crystal growth kinetics and mechanisms[J]. Frontiers of Chemical Science and Engineering, 2023 , 17(10) : 1503 -1515 . DOI: 10.1007/s11705-022-2294-4

Acknowledgements

This research received funding from the National Natural Science Foundation of China (Grant Nos. 22278070, 21978047, and 21776046).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-022-2294-4 and is accessible for authorized users.
1
Babu N J, Nangia A. Solubility advantage of amorphous drugs and pharmaceutical cocrystals. Crystal Growth & Design, 2011, 11(7): 2662–2679

DOI

2
Thayer A M. Finding solutions. Chemical and Engineering News, 2010, 88(22): 13–18

DOI

3
Malek M A H, Patel P M. Diverse strategies to boost up solubility of poor water soluble drugs a review. International Journal of Pharmaceutical Sciences and Research, 2020, 11(11): 5346–5359

4
Kumar R. Nanotechnology based approaches to enhance aqueous solubility and bioavailability of griseofulvin: a literature survey. Journal of Drug Delivery Science and Technology, 2019, 53: 101221

DOI

5
Chen H J, Pui Y S, Liu C Y, Chen Z, Su C C, Hageman M, Hussain M, Haskell R, Stefanski K, Foster K, Gudmundsson O, Qian F. Moisture-induced amorphous phase separation of amorphous solid dispersions: molecular mechanism, microstructure, and its impact on dissolution performance. Journal of Pharmaceutical Sciences, 2018, 107(1): 317–326

DOI

6
Yang M Y, Gong W, Wang Y L, Shan L, Li Y, Gao C S. Bioavailability improvement strategies for poorly water-soluble drugs based on the supersaturation mechanism: an update. Journal of Pharmacy & Pharmaceutical Sciences, 2016, 19(2): 208–225

DOI

7
Sharma A, Arora K, Mohapatra H, Sindhu R K, Bulzan M, Cavalu S, Paneshar G, Elansary H O, El-Sabrout A M, Mahmoud E A, Alaklabi A. Supersaturation-based drug delivery systems: strategy for bioavailability enhancement of poorly water-soluble drugs. Molecules, 2022, 27(9): 2969

DOI

8
Shi Q, Li F, Yeh S, Wang Y A, Xin J B. Physical stability of amorphous pharmaceutical solids: nucleation, crystal growth, phase separation and effects of the polymers. International Journal of Pharmaceutics, 2020, 590: 119925

DOI

9
Alonzo D E, Zhang G G Z, Zhou D L, Gao Y, Taylor L S. Understanding the behavior of amorphous pharmaceutical systems during dissolution. Pharmaceutical Research, 2010, 27(4): 608–618

DOI

10
Sunagawa. Crystals: Growth, Morphology, & Perfection. Cambridge: Cambridge University, 2007

11
Na H S, Oh S J. A comparison of crystal growth kinetics by use of chemical potential difference and concentration difference. Korean Journal of Chemical Engineering, 1996, 13(4): 343–350

DOI

12
Weng J Y, Huang Y P, Hao D L, Ji Y H. Recent advances of pharmaceutical crystallization theories. Chinese Journal of Chemical Engineering, 2020, 28(4): 935–948

DOI

13
Wu Z H, Yang S L, Wu W. Shape control of inorganic nanoparticles from solution. Nanoscale, 2016, 8(3): 1237–1259

DOI

14
Ji Y H, Hao D L, Luebbert C, Sadowski G. Insights into influence mechanism of polymeric excipients on dissolution of drug formulations: a molecular interaction-based theoretical model analysis and prediction. AIChE Journal, 2021, 67(11): e17372

DOI

15
MullinJ W. Crystallization. Oxford: Butterworth-Heinemann, 1993, 216–225

16
Tai C Y, Chang M C, Wu C K, Lin Y C. Interpretation of calcite growth data using the two-step crystal growth model. Chemical Engineering Science, 2006, 61(16): 5346–5354

DOI

17
Schram C J, Smyth R J, Taylor L S, Beaudoin S P. Understanding crystal growth kinetics in the absence and presence of a polymer using a rotating disk apparatus. Crystal Growth & Design, 2016, 16(5): 2640–2645

DOI

18
Kumar K V. Regression analysis for the two-step growth kinetics of crystals in pure solutions. Industrial & Engineering Chemistry Research, 2009, 48(16): 7852–7859

DOI

19
Alonzo D E, Raina S, Zhou D, Gao Y, Zhang G G Z, Taylor L S. Characterizing the impact of hydroxypropylmethyl cellulose on the growth and nucleation kinetics of felodipine from supersaturated solutions. Crystal Growth & Design, 2012, 12(3): 1538–1547

DOI

20
Dannenfelser R M, He H, Joshi Y, Bateman S, Serajuddin A T M. Development of clinical dosage forms for a poorly water soluble drug I: application of polyethylene glycol-polysorbate 80 solid dispersion carrier system. Journal of Pharmaceutical Sciences, 2004, 93(5): 1165–1175

DOI

21
Miyazaki T, Yoshioka S, Aso Y, Kawanishi T. Crystallization rate of amorphous nifedipine analogues unrelated to the glass transition temperature. International Journal of Pharmaceutics, 2007, 336(1): 191–195

DOI

22
Warren D B, Benameur H, Porter C J H, Pouton C W. Using polymeric precipitation inhibitors to improve the absorption of poorly water-soluble drugs: a mechanistic basis for utility. Journal of Drug Targeting, 2010, 18(10): 704–731

DOI

23
Huang Z, Staufenbiel S, Bodmeier R. Kinetic solubility improvement and influence of polymers on controlled supersaturation of itraconazole-succinic acid nano-co-crystals. International Journal of Pharmaceutics, 2022, 616: 121536

DOI

24
Ueda K, Yamamoto N, Higashi K, Moribe K. NMR-based mechanistic study of crystal nucleation inhibition in a supersaturated drug solution by polyvinylpyrrolidone. Crystal Growth & Design, 2022, 22(5): 3235–3244

DOI

25
Zhao P X, Hu G W, Chen H N, Li M, Wang Y T, Sun N, Wang L L, Xu Y, Xia J L, Tian B C, Liu Y, He Z, Fu Q. Revealing the roles of polymers in supersaturation stabilization from the perspective of crystallization behaviors: a case of nimodipine. International Journal of Pharmaceutics, 2022, 616: 121538

DOI

26
Wang B, Wang D D, Zhao S, Huang X B, Zhang J B, Lv Y, Liu X C, Lv G J, Ma X J. Evaluate the ability of PVP to inhibit crystallization of amorphous solid dispersions by density functional theory and experimental verify. European Journal of Pharmaceutical Sciences, 2017, 96: 45–52

DOI

27
Mazurek A H, Szeleszczuk L, Pisklak D M. Periodic DFT calculations-review of applications in the pharmaceutical sciences. Pharmaceutics, 2020, 12(5): 415

DOI

28
Choonara B F, Choonara Y E, Kumar P, du Toit L C, Tomar L K, Tyagi C, Pillay V. A menthol-based solid dispersion technique for enhanced solubility and dissolution of sulfamethoxazole from an oral tablet matrix. AAPS PharmSciTech, 2015, 16(4): 771–786

DOI

29
Benet L Z, Broccatelli F, Oprea T I. BDDCS applied to over 900 drugs. AAPS Journal, 2011, 13(4): 519–547

DOI

30
Wu D X, Ji Y H. Influence of polymeric excipients on the solubility of aspirin: experimental measurement and model prediction. Fluid Phase Equilibria, 2020, 508: 112450

DOI

31
Chen Q, Ji Y H, Ge K. Influence of excipients on thermodynamic phase behavior of pharmaceutical/solvent systems: molecular thermodynamic model prediction. Chemical Engineering Science, 2021, 244: 116798

DOI

32
Prudic A, Lesniak A K, Ji Y H, Sadowski G. Thermodynamic phase behaviour of indomethacin/PLGA formulations. European Journal of Pharmaceutics and Biopharmaceutics, 2015, 93: 88–94

DOI

33
Gross J, Sadowski G. Perturbed-chain SAFT: an equation of state based on a perturbation theory for chain molecules. Industrial & Engineering Chemistry Research, 2001, 40(4): 1244–1260

DOI

34
Prudic A, Kleetz T, Korf M, Ji Y H, Sadowski G. Influence of copolymer composition on the phase behavior of solid dispersions. Molecular Pharmaceutics, 2014, 11(11): 4189–4198

DOI

35
Ji Y H, Lesniak A K, Prudic A, Paus R, Sadowski G. Drug release kinetics and mechanism from PLGA formulations. AIChE Journal, 2016, 62(11): 4055–4065

DOI

36
Schneider R, Taspinar L, Ji Y H, Sadowski G. The influence of polymeric excipients on desupersaturation profiles of active pharmaceutical ingredients. 1: polyethylene glycol. International Journal of Pharmaceutics, 2020, 582: 119317

DOI

37
Paus R, Prudic A, Ji Y H. Influence of excipients on solubility and dissolution of pharmaceuticals. International Journal of Pharmaceutics, 2015, 485(1−2): 277–287

DOI

38
Ward C A, Rizk M, Tucker A S. Statistical rate theory of interfacial transport. 2. Rate of isothermal bubble evolution in a liquid gas solution. Journal of Chemical Physics, 1982, 76(11): 5606–5614

DOI

39
Ward C A, Findlay R D, Rizk M. Statistical rate theory of interfacial transport. 1. Theoretical development. Journal of Chemical Physics, 1982, 76(11): 5599–5605

DOI

40
Dejmek M, Ward C A. A statistical rate theory study of interface concentration during crystal growth or dissolution. Journal of Chemical Physics, 1998, 108(20): 8698–8704

DOI

41
Skotnicki M, Jadach B, Skotnicka A, Milanowski B, Tajber L, Pyda M, Kujawski J. Physicochemical characterization of a co-amorphous atorvastatin-irbesartan system with a potential application in fixed-dose combination therapy. Pharmaceutics, 2021, 13(1): 118

DOI

42
Sagdinc S G, Esme A. Theoretical and vibrational studies of 4,5-diphenyl-2–2 oxazole propionic acid (oxaprozin). Spectrochimica Acta, 2010, 75(4): 1370–1376

DOI

43
Lu T, Chen F W. Quantitative analysis of molecular surface based on improved marching tetrahedra algorithm. Journal of Molecular Graphics & Modelling, 2012, 38: 314–323

DOI

44
Xantheas S S. On the importance of the fragment relaxation energy terms in the estimation of the basis set superposition error correction to the intermolecular interaction energy. Journal of Chemical Physics, 1996, 104(21): 8821–8824

DOI

45
Price C P, Grzesiak A L, Matzger A J. Crystalline polymorph selection and discovery with polymer heteronuclei. Journal of the American Chemical Society, 2005, 127(15): 5512–5517

DOI

46
Patyk-Kazmierczak E, Kazmierczak M. Hydrate vs anhydrate under a pressure-(de)stabilizing effect of the presence of water in solid forms of sulfamethoxazole. Crystal Growth & Design, 2021, 21(12): 6879–6888

DOI

47
Healy A M, Worku Z A, Kumar D, Madi A M. Pharmaceutical solvates, hydrates and amorphous forms: a special emphasis on cocrystals. Advanced Drug Delivery Reviews, 2017, 117: 25–46

DOI

Outlines

/