Acetone-assisted co-processing of meloxicam with amino acids for enhanced dissolution rate

References

• Abd Elbary A, Ali A, Aboud HM. 2012. Enhanced dissolution of meloxicam from orodispersible tablets prepared by different methods. Bull Fac Pharm Cairo Univ. 50(2):89–97.
   Google Scholar
• Alshaikh RA, Essa EA, El Maghraby GM. 2019. Eutexia for enhanced dissolution rate and anti-inflammatory activity of nonsteroidal anti-inflammatory agents: caffeine as a melting point modulator. Int J Pharm. 563:395–405.
   PubMedGoogle Scholar
• Arafa MF, El-Gizawy SA, Osman MA, El Maghraby GM. 2017. Co-crystallization for enhanced dissolution rate of nateglinide: in vitro and in vivo evaluation. J Drug Deliv Sci Technol. 38:9–17.
   Web of Science ®Google Scholar
• Arafa MF, El-Gizawy SA, Osman MA, El Maghraby GM. 2018. Xylitol as a potential co-crystal co-former for enhancing dissolution rate of felodipine: preparation and evaluation of sublingual tablets. Pharm Dev Technol. 23(5):454–463.
   PubMed Web of Science ®Google Scholar
• Bartos C, Ambrus R, Katona G, Sovány T, Gáspár R, Márki A, Ducza E, Ivanov A, Tömösi F, Janáky T, et al. 2019. Transformation of meloxicam containing nanosuspension into surfactant-free solid compositions to increase the product stability and drug bioavailability for rapid analgesia. DDDT. 13:4007–4020.
   PubMed Web of Science ®Google Scholar
• Berry DJ, Steed JW. 2017. Pharmaceutical cocrystals, salts and multicomponent systems; intermolecular interactions and property based design. Adv Drug Deliv Rev. 117:3–24.
   PubMed Web of Science ®Google Scholar
• Cheney ML, Weyna DR, Shan N, Hanna M, Wojtas L, Zaworotko MJ. 2011. Coformer selection in pharmaceutical cocrystal development: a case study of a meloxicam aspirin cocrystal that exhibits enhanced solubility and pharmacokinetics. J Pharm Sci. 100(6):2172–2181.
   PubMed Web of Science ®Google Scholar
• El-Gizawy SA, Osman MA, Arafa MF, El Maghraby GM. 2015. Aerosil as a novel co-crystal co-former for improving the dissolution rate of hydrochlorothiazide. Int J Pharm. 478(2):773–778.
   PubMedGoogle Scholar
• Elshaer A, Khan S, Perumal D, Hanson P, Mohammed AR. 2011. Use of amino acids as counterions improves the solubility of the BCS II model drug, indomethacin. CDD. 8(4):363–372.
   PubMed Web of Science ®Google Scholar
• Engelhardt G, Homma D, Schlegel K, Utzmann R, Schnitzler C. 1995. Antiinflammatory, analgesic, antipyretic and related properties of meloxicam, a new nonsteroidal antiinflammatory agent with favorable gastrointestinal tolerance. Inflamm Res. 44(10):423–433.
   PubMed Web of Science ®Google Scholar
• Foces-Foces C, Roux MV, Notario R, Segura M. 2011. Thermal behavior and polymorphism in medium–high temperature range of the sulfur containing amino acids l-cysteine and l-cystine. J Therm Anal Calorim. 105(3):747–756.
   Web of Science ®Google Scholar
• Fujisawa H, Okada H, Miura Y, Fujita M, Shimamoto T. 1976. Arginine and lysine salts of acid cephalosporin. US patent 3984403.
   Google Scholar
• Fuliaş A, Vlase G, Ledeţi I, Şuta LM. 2015. Ketoprofen–cysteine equimolar salt synthesis, thermal analysis, PXRD and FTIR spectroscopy investigation. J Therm Anal Calorim. 121(3):1087–1091.
   Web of Science ®Google Scholar
• Ghareeb MM, Abdulrasool AA, Hussein AA, Noordin MI. 2009. Kneading technique for preparation of binary solid dispersion of meloxicam with poloxamer 188. AAPS PharmSciTech. 10(4):1206–1215.
   PubMed Web of Science ®Google Scholar
• Ghorab MM, Abdel-Salam HM, El-Sayad MA, Mekhel MM. 2004. Tablet formulation containing meloxicam and beta-cyclodextrin: mechanical characterization and bioavailability evaluation. AAPS PharmSciTech. 5(4):63–68.
   Web of Science ®Google Scholar
• Gómez-Zavaglia A, Fausto R. 2003. Low-temperature solid-state FTIR study of glycine, sarcosine and N,N-dimethylglycine: observation of neutral forms of simple α-amino acids in the solid state. Phys Chem Chem Phys. 5(15):3154–3161.
   Web of Science ®Google Scholar
• Huang F, Lan Y, Chen P. 2011. Synthesis and characterization of water-soluble L-cysteine-modified ZnS nanocrystals doped with silver. J Mater Sci. 46(17):5732–5736.
   Web of Science ®Google Scholar
• Jacon Freitas JT, Santos Viana OMM, Bonfilio R, Doriguetto AC, de Araujo MB. 2017. Analysis of polymorphic contamination in meloxicam raw materials and its effects on the physicochemical quality of drug product. Eur J Pharm Sci. 109:347–358.
   PubMed Web of Science ®Google Scholar
• Jafar M, Dehghan MHG, Shareef A. 2010. Enhancement of dissolution and anti-infammatory effect of meloxicam using solid dispersions. Int J App Pharm. 2:22–27.
   Google Scholar
• Jensen KT, Blaabjerg LI, Lenz E, Bohr A, Grohganz H, Kleinebudde P, Rades T, Löbmann K. 2016. Preparation and characterization of spray-dried co-amorphous drug–amino acid salts. J Pharm Pharmacol. 68(5):615–624.
   PubMed Web of Science ®Google Scholar
• Karagianni A, Malamatari M, Kachrimanis K. 2018. Pharmaceutical cocrystals: new solid phase modification approaches for formulation of APIs. Pharmaceutics. 10(1):18–32.
   Web of Science ®Google Scholar
• Kasten G, Lobo L, Dengale S, Grohganz H, Rades T, Löbmann K. 2018. In vitro and in vivo comparison between crystalline and co-amorphous salts of naproxen-arginine. Eur J Pharm Biopharm. 132:192–199.
   PubMed Web of Science ®Google Scholar
• Kasten G, Nouri K, Grohganz H, Rades T, Löbmann K. 2017. Performance comparison between crystalline and co-amorphous salts of indomethacin-lysine. Int J Pharm. 533(1):138–144.
   PubMedGoogle Scholar
• Khan KA. 1975. The concept of dissolution efficiency. J Pharm Pharmacol. 27(1):48–49.
   PubMed Web of Science ®Google Scholar
• Löbmann K, Grohganz H, Laitinen R, Strachan C, Rades T. 2013. Amino acids as co-amorphous stabilizers for poorly water soluble drugs – Part 1: preparation, stability and dissolution enhancement. Eur J Pharm Biopharm. 85(3):873–881.
   PubMed Web of Science ®Google Scholar
• Luger P, Daneck K, Engel W, Trummlitz G, Wagner K. 1996. Structure and physicochemical properties of meloxicam, a new NSAID. Eur J Pharm Sci. 4(3):175–187.
   Web of Science ®Google Scholar
• Pellegata RL. 1993. Furosamide salts. US patent 5182300.
   Google Scholar
• PetrušEvski G, Naumov Pe, Jovanovski Gligor, Bogoeva-Gaceva Gordana, Ng Seik Weng. 2008. Solid-state forms of sodium valproate, active component of the anticonvulsant drug epilim. Chem Med Chem. 3(9):1377–1386.
   Google Scholar
• Sapte S, Yogesh Pore Y. 2016. Inclusion complexes of cefuroxime axetil with β-cyclodextrin: physicochemical characterization, molecular modeling and effect of l-arginine on complexation. J Pharm Anal. 6(5):300–306.
   PubMed Web of Science ®Google Scholar
• Shervington A, Al-Tayyem R. 2001. Arginine. In: H.G. Brittian, editor. Analytical profiles of drug substances and excipients, vol. 27. New York: Academic Press. p. 1–32.
   Google Scholar
• Shete A, Murthy S, Korpale S, Yadav A, Sajane S, Sakhare S, Doijad R. 2015. Cocrystals of itraconazole with amino acids: screening, synthesis, solid state characterization, in vitro drug release and antifungal activity. J Drug Deliv Sci Technol. 28:46–55.
   Web of Science ®Google Scholar
• Song Q, Shen C, Shen B, Lian W, Liu X, Dai B, Yuan H. 2018. Development of a fast dissolving sublingual film containing meloxicam nanocrystals for enhanced dissolution and earlier absorption. J Drug Deliv Sci Technol. 43:243–252.
   Web of Science ®Google Scholar
• Song Y, Wang LY, Liu F, Li YT, Wu ZY, Yan CW. 2019. Simultaneously enhancing the in vitro/in vivo performances of acetazolamide using proline as a zwitterionic coformer for cocrystallization. Cryst Eng Commun. 21(19):3064–3073.
   Google Scholar
• Tari T, Fekete Z, Szabo-Revesz P, Aigner Z. 2015. Reduction of glycine particle size by impinging jet crystallization. Int J Pharm. 478(1):96–102.
   PubMedGoogle Scholar
• Tong W-QT, Whitesell G. 1998. In situ salt screening-a useful technique for discovery support and preformulation studies. Pharm Dev Technol. 3(2):215–223.
   PubMedGoogle Scholar
• Umesh M, Naveen S, Amit C. 2012. Physical properties and dissolution behaviour of meloxicam/poloxamer solid dispersions prepared by hot melt method and microwave assisted method. Int J Res Pharm Sci. 2:64–74.
   Google Scholar
• Weyna David R, Cheney Miranda L, Shan Ning, Hanna Mazen, Zaworotko Michael J, Sava Vasyl, Song Shijie, Sanchez-Ramos Juan R. 2012. Improving solubility and pharmacokinetics of meloxicam via multiple-component crystal formation. Mol Pharm. 9(7):2094–2102.
   PubMedGoogle Scholar
• Zhang L, Wu C, Gu T, Zhang Y, Liu Y. 2014. Preparation, characterization and cytotoxic activity of rhein argininate. Anal Methods. 6(11):3838–3841.
   Web of Science ®Google Scholar