Drug salt formation via mechanochemistry: The case study of vincamine

Molecular Pharmaceutics

Volumn 10, Issue 1, 2013, Pages 211-224

  Hasa, Dritan ^a   Perissutti, Beatrice ^a   Cepek, Cinzia ^b   Bhardwaj, Sunil ^b   Carlino, Elvio ^b   Grassi, Mario ^a   Invernizzi, Sergio ^a   Voinovich, Dario ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

^b IOM CNR LABORATORIO TASC   (Italy)

Author keywords

bioequivalence; HRTEM; mechanochemistry; solid excipient; solid state; stability; vincamine salt citrate; XPS

Indexed keywords

CARBOXYMETHYLCELLULOSE; CITRIC ACID; CRYSTALLIN; SODIUM CHLORIDE; VINCAMINE;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL REACTION; CHEMISTRY; CONTROLLED STUDY; EXPERIMENTAL DESIGN; HYDROPHILICITY; IN VITRO STUDY; IN VIVO STUDY; MECHANOCHEMISTRY; NONHUMAN; PRIORITY JOURNAL; RAT; SALIFICATION; SOLID STATE; SOLUBILIZATION; STATISTICAL ANALYSIS; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; VINCA; X RAY PHOTOELECTRON SPECTROSCOPY; X RAY POWDER DIFFRACTION;

ANIMALS; BIOLOGICAL AVAILABILITY; CHEMISTRY, PHARMACEUTICAL; CITRIC ACID; DRUG STABILITY; EXCIPIENTS; KINETICS; PARTICLE SIZE; PHOTOELECTRON SPECTROSCOPY; PILOT PROJECTS; RATS; RATS, SPRAGUE-DAWLEY; SALTS; SOLUBILITY; SOLVENTS; VINCAMINE; X-RAY DIFFRACTION;

EID: 84872167600     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp300371f     Document Type: Article

References (36)

1. Serajuddin, A. T. M. Salt formation to improve drug solubility Adv. Drug Delivery Rev. 2007, 59, 603-616
2. Stephenson, G. A.; Aburub, A.; Woods, T. A. Physical stability of salts of week bases in the solid state J. Pharm. Sci. 2011, 100 (5) 1607-1617
3. g) during lyophilization of ganciclovir salt forms Mol. Pharmaceutics 2011, 8 (1) 309-314
4. Boldyrev, V. V. Control of the reactivity of solids Annu. Rev. Mater. Sci. 1979, 9, 455-469
5. James, S. L.; Adams, C. J.; Bolm, C.; Braga, D.; Collier, P.; Friscic, T.; Grepioni, F.; Harris, K. D. M.; Hyett, G.; Jones, W.; Krebs, A.; Mack, J.; Maini, L.; Orpen, A. G.; Parkin, I. P.; Shearouse, W. C.; Steed, J. W.; Waddell, D. C. Mechanochemistry: opportunities for new and cleaner synthesis Chem. Soc. Rev. 2012, 41, 413-447
6. Shakhtshneider, T. P.; Boldyrev, V. V. Mechanochemical synthesis and mechanical activation of drugs. In Reactivity of molecular solids; Boldyreva, E.; Boldyrev, V., Eds.; Wiley: 1999; pp 271-311.
7. Trask, A. V.; Haynes, D. A.; Motherwell, W. D. S.; Jones, W. Screening for crystalline salts via mechanochemistry Chem. Commun. 2006, 51, 51-53
8. André, V.; Braga, D.; Grepioni, F.; Duarte, M. T. Crystal forms of the antibiotic 4-aminosalicylic acid: solvates and molecular salts with dioxane, morpholine and piperazine Cryst. Growth Des. 2009, 9, 5108-5116
9. Friscic, T.; Reid, D,G.; Day, D. M.; Duer, M. J.; Jones, W. Effect of fluorination on molecular conformation in the solid state: tuning the conformation of cocrystal formers Cryst. Growth Des. 2009, 11, 972-981
10. Sharmarke, M.; Tocher, D. A.; Vickers, M.; Karamerttzanis, P. G.; Price, S. L. Salt or cocrystal? A new series of crystal structures formed from simple pyridines and carboxylic acids Cryst. Growth Des. 2009, 9, 2881-2889
11. Hasa, D.; Voinovich, D.; Perissutti, B.; Grassi, M.; Bonifacio, A.; Sergo, V.; Cepek, C.; Chierotti, M. R.; Gobetto, R.; Dall'Acqua, S.; Invernizzi, S. Enhanced oral bioavailability of vinpocetine through mechanochemical salt formation: physico-chemical characterization and in vivo studies Pharm. Res. 2011, 28, 1870-1883
12. Karpati, E.; Biro, K.; Kukorelli, T. Investigation of vasoactive agents with indole skeletons at Richter Ltd Acta Pharm. Hung. 2002, 72, 25-36
13. Vas, A.; Gulyas, B. Eburnamine derivatives and the brain Med. Res. Rev. 2005, 25, 737-757
14. Vereczkey, L. Pharmacokinetics and metabolism of vincamine and related compounds Eur. J. Drug Metab. Pharmacokinet. 1985, 10, 89-103
15. Emara, L. H.; El-Menshawi, B. S.; Estefan, M. Y. In vitro-In vivo correlation and comparative bioavailability of vincamine in prolonged-release preparations Drug Dev. Ind. Pharm. 2000, 26, 243-251
16. Ritschel, W. A.; Agrawala, P. Biopharmaceutic and pharmacokinetic aspects of vincamine HCl Methods Find. Exp. Clin. Pharmacol. 1985, 7, 129-136
17. Voinovich, D.; Perissutti, B.; Grassi, M.; Passerini, N.; Bigotto, A. Solid State mechanochemical activation of silybum marianum dry extract with β-cyclodextrins: characterization and bioavailability of the coground systems J. Pharm. Sci. 2009, 98 (11) 4119-4129
18. Mathieu, D.; Nony, J.; Phan-Tan-Luu, R. NEMRODW (New Efficient Technology for Research using Optimal Design) software; LPRAI: Marseille, 1999.
19. R Development Core Team. R: A language and environment for statistical computing. R Foundation for Statistical Computing. Wien, Austria; ISBN 3-900051-07-0; 2009. Available from: http://www.R-project.org (accessed on May 30, 2012).
20. Stadelmann, P. A. EMS-a software package for electron diffraction analysis and HREM image simulation in materials science Ultramicroscopy 1987, 21 (2) 131-145
21. Allen, F. H.; Kennard, O.; Taylor, R. Systematic analysis of structural data as a research technique in organic chemistry Acc. Chem. Res. 1983, 16 (5) 146-153
22. Hasa, D.; Perissutti, B.; Chierotti, M. R.; Gobetto, R.; Grabnar, I.; Bonifacio, A.; Dall'Acqua, S.; Invernizzi, S.; Voinovich, D. Mechanochemically induced disordered structures of vincamine: the different mediation of two cross-linked polymers Int. J. Pharm. 2012, 436, 41-57
23. Sun, D. D.; Ju, T. R.; Lee, P. I. Enhanced kinetic solubility profiles of indomethacin amorphous solid dispersions in poly(2-hydroxyethyl methacrylate) hydrogels Eur. J. Pharm. Biopharm. 2012, 81, 149-158
24. Van Eerdenbrugh, B.; Alonzo, D. E.; Taylor, L. S. Influence of particle size on the ultraviolet Spectrum of particulate-containing solutions: implications for in-situ concentration monitoring using UV/Vis fiber-optic probes Pharm. Res. 2011, 28, 1643-1652
25. Cadelli, G.; Zarattini, P. Further refinements of tail artery cannulation in conscious rats. FELASA-ICLAS Joint Meeting, 2007, Villa Erba, Cernobbio (CO), Italy.
26. Childs, S. L.; Patrick Stahly, G.; Park, A. The salt-cocrystal continuum: the influence of crystal structure on ionization state Mol. Pharmaceutics 2007, 4, 323-338
27. Black, S. N.; Collier, E. A.; Davey, R. J.; Roberts, R. J. Structure, solubility, screening, and synthesis of molecular salts J. Pharm. Sci. 2007, 96 (5) 1053-1068
28. Lu, Q.; Zografi, G. Properties of the citric acid at the glass transition J. Pharm. Sci. 1997, 86 (12) 1374-1378
29. Kibbe, A. H. Handbook of pharmaceutical excipients, 3 rd ed.; American Pharmaceutical Association: Washington, DC, 2000; pp 87-90.
30. Colombo, I.; Grassi, G.; Grassi, M. Drug Mechanochemical Activation J. Pharm. Sci. 2009, 98 (11) 3961-3986
31. Guerrieri, P.; Taylor, L. S. Role of salt and excipient properties on disproportionation in the solid-state Pharm. Res. 2009, 26, 2015-2026
32. Stevens, S. J.; Byard, S. J.; Muryn, C. A.; Schroeder, S. L. M. Identification of protonation state by XPS, solid-state NMR and DFT: characterization the nature of a new theophylline by experimental and computational methods J. Phys. Chem. B 2010, 114, 13961-13969
33. Stevens, S. J.; Byard, S. J.; Schroeder, S. L. M. Salt or co-crystal? Determination of protonation state by X-Ray Photoelectron Spectroscopy (XPS) J. Pharm. Sci. 2010, 99 (11) 4453-4457
34. Boldyrev, V. V. Mechanochemistry and mechanical activation of solids Russ. Chem. Rev. 2006, 75 (3) 177-189
35. Friscic, T.; Jones, W. Recent advances in understanding the mechanism of cocrystal formation via grinding Cryst. Growth Des. 2009, 9, 1621-1637
36. Alonzo, D. E.; Zhang, G. G. Z.; Zhou, D.; Gao, Y.; Taylor, L. S. Understanding the behavior of amorphous pharmaceutical systems during dissolution Pharm. Res. 2009, 27 (4) 608-618