Studying the Complex Formation of Sulfonatocalix[4]naphthalene and Meloxicam Towards Enhancing Its Solubility and Dissolution Performance

Overview

Journal Pharmaceutics

Publisher MDPI

Date 2021 Jul 2

PMID 34209201

Citations 2

Authors

Tayel A Al Hujran

Mousa K Magharbeh

Samer Al-Gharabli

Rula R Haddadin

Manal N Al Soub

Hesham M Tawfeek

Affiliations

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Abstract

The interaction between meloxicam and sulfonatocalix [4] naphthalene was investigated to improve the meloxicam solubility and its dissolution performance. Solubility behavior was investigated in distilled water (DW) and at different pH conditions. Besides, solid systems were prepared in a 1:1 molar ratio using coevaporate, kneading, and simple physical mixture techniques. Further, they were characterized by PXRD, FT-IR, DCS, and TGA. In vitro dissolution rate for coevaporate, kneaded, and physical mixture powders were also investigated. Solubility study revealed that meloxicam solubility significantly increased about 23.99 folds at phosphate buffer of pH 7.4 in the presence of sulfonatocalix [4] naphthalene. The solubility phase diagram was classified as A type, indicating the formation of 1:1 stoichiometric inclusion complex. PXRD, FT-IR, DCS, and TGA pointed out the formation of an inclusion complex between meloxicam and sulfonatocalix [4] naphthalene solid powders prepared using coevaporate technique. In addition, in vitro meloxicam dissolution studies revealed an improvement of the drug dissolution rate. Furthermore, a significantly higher drug release ( ≤ 0.05) and a complete dissolution was achieved during the first 10 min compared with the other solid powders and commercial meloxicam product. The coevaporate product has the highest increasing dissolution fold and RDR in the investigated media, with average values ranging from 5.4-65.28 folds and 7.3-90.7, respectively. In conclusion, sulfonatocalix [4] naphthalene is a promising host carrier for enhancing the solubility and dissolution performance of meloxicam with an anticipated enhanced bioavailability and fast action for acute and chronic pain disorders.

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References

Saokham P, Muankaew C, Jansook P, Loftsson T . Solubility of Cyclodextrins and Drug/Cyclodextrin Complexes. Molecules. 2018; 23(5). PMC: 6099580. DOI: 10.3390/molecules23051161. View

Newman A, Zografi G . Commentary: Considerations in the Measurement of Glass Transition Temperatures of Pharmaceutical Amorphous Solids. AAPS PharmSciTech. 2019; 21(1):26. PMC: 6917632. DOI: 10.1208/s12249-019-1562-1. View

Salem L, El-Feky G, Fahmy R, El Gazayerly O, Abdelbary A . Coated Lipidic Nanoparticles as a New Strategy for Enhancing Nose-to-Brain Delivery of a Hydrophilic Drug Molecule. J Pharm Sci. 2020; 109(7):2237-2251. DOI: 10.1016/j.xphs.2020.04.007. View

Zhu X, Wang H, Chen Q, Yang W, Yang G . Preparation and characterization of inclusion complex of iprodione and beta-cyclodextrin to improve fungicidal activity. J Agric Food Chem. 2007; 55(9):3535-9. DOI: 10.1021/jf070197f. View

Jin C, Zhao C, Shen D, Dong W, Liu H, He Z . Evaluating bioequivalence of meloxicam tablets: is in-vitro dissolution test overdiscriminating?. J Pharm Pharmacol. 2017; 70(2):250-258. DOI: 10.1111/jphp.12859. View

AlHujran T, Dawe L, Collins J, Georghiou P . Synthesis and clathrates of oligomeric 2-O-naphthoide macrocycles. J Org Chem. 2011; 76(3):971-3. DOI: 10.1021/jo101959w. View

Tawfeek H, Hassan Y, Aldawsari M, Fayed M . Enhancing the Low Oral Bioavailability of Sulpiride via Fast Orally Disintegrating Tablets: Formulation, Optimization and In Vivo Characterization. Pharmaceuticals (Basel). 2020; 13(12). PMC: 7762047. DOI: 10.3390/ph13120446. View

Karagianni A, Kachrimanis K, Nikolakakis I . Co-Amorphous Solid Dispersions for Solubility and Absorption Improvement of Drugs: Composition, Preparation, Characterization and Formulations for Oral Delivery. Pharmaceutics. 2018; 10(3). PMC: 6161132. DOI: 10.3390/pharmaceutics10030098. View

Espanol E, Maldonado Villamil M . Calixarenes: Generalities and Their Role in Improving the Solubility, Biocompatibility, Stability, Bioavailability, Detection, and Transport of Biomolecules. Biomolecules. 2019; 9(3). PMC: 6468619. DOI: 10.3390/biom9030090. View

10.

Ahmed M, Khanna D, Furst D . Meloxicam in rheumatoid arthritis. Expert Opin Drug Metab Toxicol. 2006; 1(4):739-51. DOI: 10.1517/17425255.1.4.739. View

11.

Da Silva E, Shahgaldian P, Coleman A . Haemolytic properties of some water-soluble para-sulphonato-calix-[n]-arenes. Int J Pharm. 2004; 273(1-2):57-62. DOI: 10.1016/j.ijpharm.2003.12.008. View

12.

Chacko I, Ghate V, Dsouza L, Lewis S . Lipid vesicles: A versatile drug delivery platform for dermal and transdermal applications. Colloids Surf B Biointerfaces. 2020; 195:111262. DOI: 10.1016/j.colsurfb.2020.111262. View

13.

Yang W, de Villiers M . Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes. J Pharm Pharmacol. 2004; 56(6):703-8. DOI: 10.1211/0022357023439. View

14.

Lu D, Huang Q, Wang S, Wang J, Huang P, Du P . The Supramolecular Chemistry of Cycloparaphenylenes and Their Analogs. Front Chem. 2019; 7:668. PMC: 6794338. DOI: 10.3389/fchem.2019.00668. View

15.

Aoki T, Yamaguchi H, Naito H, Shiiki K, Izawa K, Ota Y . Premedication with cyclooxygenase-2 inhibitor meloxicam reduced postoperative pain in patients after oral surgery. Int J Oral Maxillofac Surg. 2006; 35(7):613-7. DOI: 10.1016/j.ijom.2006.01.026. View

16.

Khan K . The concept of dissolution efficiency. J Pharm Pharmacol. 1975; 27(1):48-9. DOI: 10.1111/j.2042-7158.1975.tb09378.x. View

17.

Pairet M, Van Ryn J, Schierok H, Mauz A, Trummlitz G, Engelhardt G . Differential inhibition of cyclooxygenases-1 and -2 by meloxicam and its 4'-isomer. Inflamm Res. 1998; 47(6):270-6. DOI: 10.1007/s000110050329. View

18.

Crini G . Review: a history of cyclodextrins. Chem Rev. 2014; 114(21):10940-75. DOI: 10.1021/cr500081p. View

19.

Goldman A, Williams C, Sheng H, Lamps L, WILLIAMS V, Pairet M . Meloxicam inhibits the growth of colorectal cancer cells. Carcinogenesis. 1999; 19(12):2195-9. DOI: 10.1093/carcin/19.12.2195. View

20.

Kumar P, Mohan C, Kanamsrinivasan Uma Shankar M, Gulati M . Physiochemical Characterization and Release Rate Studies of SolidDispersions of Ketoconazole with Pluronic F127 and PVP K-30. Iran J Pharm Res. 2013; 10(4):685-94. PMC: 3813076. View