A new method of producing monoclinic paracetamol suitable for direct compression

Pharmaceutical Research

Volumn 28, Issue 12, 2011, Pages 3116-3127

  Ogienko, Andrey G ^a,b   Boldyreva, Elena V ^a,c   Yu Manakov, Andrey ^a,b   Boldyrev, Vladimir V ^a,c   Yunoshev, Alexander S ^a,d   Ogienko, Anna A ^a,e   Myz, Svetlana A ^a,c   Ancharov, Alexei I ^a,c   Achkasov, Andrey F ^a   Drebushchak, Tatiana N ^a,c  

^a NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

^b NIKOLAEV INSTITUTE OF INORGANIC CHEMISTRY   (Russian Federation)

^c INSTITUTE OF SOLID STATE CHEMISTRY AND MECHANOCHEMISTRY   (Russian Federation)

^d LAVRENTYEV INSTITUTE OF HYDRODYNAMICS   (Russian Federation)

^e INSTITUTE OF CYTOLOGY AND GENETICS   (Russian Federation)

Author keywords

direct compression; freeze drying; microparticles; paracetamol; polymorphs; X ray diffraction

Indexed keywords

ACETONE; EXCIPIENT; LIQUID NITROGEN; PARACETAMOL; SOLVENT; WATER;

AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; COOLING; DRUG MIXTURE; DRUG STABILITY; DRUG STORAGE; ELECTRON MICROSCOPY; FREEZE DRYING; PARTICLE SIZE; PHYSICAL PARAMETERS; PRIORITY JOURNAL; PROCESS OPTIMIZATION; TABLET COMPRESSION; TABLET MANUFACTURE; THICKNESS; X RAY POWDER DIFFRACTION;

ACETAMINOPHEN; ACETONE; ANALGESICS, NON-NARCOTIC; CHEMISTRY, PHARMACEUTICAL; FREEZE DRYING; POROSITY; POWDER DIFFRACTION; SOLVENTS; WATER; X-RAY DIFFRACTION;

EID: 83555174465     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-011-0502-x     Document Type: Article

References (42)

1. EV Boldyreva VA Drebushchak IE Paukov YA Kovalevskaya TN Drebushchak 2004 DSC and adiabatic calorimetry study of the polymorphs of paracetamol - an old problem revisited J Therm Anal Calorim. 77 607 23 10.1023/B:JTAN.0000038998. 47606.27 1:CAS:528:DC%2BD2cXmvFSmtLc%3D
2. M Haisa S Kashino R Kawai H Maeda 1976 The monoclinic form of p-hydroxyacetanilamide Acta Crystallogr. B32 1283 5 1:CAS:528:DyaE28XhvVOqs7w%3D
3. G Nichols CS Frampton 1998 Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution J Pharm Sci. 87 684 93 9607944 10.1021/js970483d 1:CAS:528:DyaK1cXivVOltLY%3D (Pubitemid 28268566)
4. E Joiris P Di Martino C Berneron AM Guyot-Hermann JC Guyot 1998 Compression behavior of orthorhombic paracetamol Pharm Res. 15 1122 30 9688070 10.1023/A:1011954800246 1:CAS:528:DyaK1cXkvVWgu78%3D (Pubitemid 28356933)
5. M Haisa S Kashino R Kawai H Maeda 1974 The Orthorombic form of p-Hydroxyacetanilamide Acta Crystallogr. B30 2510 2
6. AA Politov VG Kostrovskii VV Boldyrev 2001 Conditions of preparation and crystallization of amorphous paracetamol Russ J Phys Chem. 75 1903 11
7. MA Mikhailenko 2004 Growth of large single crystals of the orthorhombic paracetamol J Cryst Growth. 265 616 8 10.1016/j.jcrysgro.2004.02.091 1:CAS:528:DC%2BD2cXjtF2qsb8%3D
8. K Kachrimanis K Fucke M Noisternig B Siebenhaar UJ Griesser 2008 Effects of moisture and residual solvent on the phase stability of orthorhombic paracetamol Pharm Res. 25 1440 9 18183475 10.1007/s11095-007-9529-4 1:CAS:528:DC%2BD1cXltFCjsL8%3D
9. P Espeau R Ceolin JL Tamarit MA Perrin JP Gauchi F Leveiller 2005 Polymorphism of paracetamol: relative stabilities of the monoclinic and orthorhombic phases inferred from topological pressure-temperature and temperature-volume phase diagrams J Pharm Sci. 94 524 39 15627255 10.1002/jps.20261 1:CAS:528:DC%2BD2MXisVWhsL4%3D (Pubitemid 40480966)
10. EV Boldyreva TP Shakhtshneider H Ahsbahs H Sowa H Uchtmann 2002 Effect of high pressure on the polymorphs of paracetamol J Therm Anal Calorim. 68 437 52 10.1023/A:1016079400592 1:CAS:528:DC%2BD38XkvFegsr4%3D (Pubitemid 34617609)
11. Z Saska J Dredan E Balogh O Luhn G Shafir I Antal 2010 Effect of isomalt as novel binding agent on compressibility of poorly compactable paracetamol evaluated by factorial design Powder Technol. 201 123 9 10.1016/j.powtec.2010. 03.009 1:CAS:528:DC%2BC3cXlvVSrtLg%3D
12. JC Wlosnewski M Kumpugdee-Vollrath P Sriamornsak 2010 Effect of drying technique and disintegrant on physical properties and drug release behavior of microcrystalline cellulose-based pellets prepared by extrusion/spheronization Chem Eng Res Des. 88 100 8 10.1016/j.cherd.2009.07.001 1:CAS:528: DC%2BC3cXhslaltb0%3D
13. H Mohammed BJ Briscoe KG Pitt 2006 The intrinsic nature and the coherence of compacted pure pharmaceutical tablets Powder Technol. 165 11 21 10.1016/j.powtec.2006.03.010 1:CAS:528:DC%2BD28XlvF2kurg%3D (Pubitemid 43949161)
14. HA Garekani JL Ford MH Rubinstein AR Rajabi-Siahboomi 2000 Highly compressible paracetamol: I: crystallization and characterization Int J Pharm. 208 87 99 11064214 10.1016/S0378-5173(00)00550-0 1:CAS:528:DC%2BD3cXosVGjtr8%3D
15. Y Gonnissen JP Remon C Vervaet 2007 Development of directly compressible powders via co-spray drying Eur J Pharm Biopharm. 67 220 6 17317123 10.1016/j.ejpb.2006.12.021 1:CAS:528:DC%2BD2sXntF2murY%3D (Pubitemid 46991327)
16. JS Boateng KH Matthews AD Auffret MJ Humphrey HN Stevens GM Eccleston 2009 In vitro drug release studies of polymeric freeze-dried wafers and solvent-cast films using paracetamol as a model soluble drug Int J Pharm. 378 66 72 19477255 10.1016/j.ijpharm.2009.05.038 1:CAS:528:DC%2BD1MXovFOjsL4%3D
17. JS Boateng AD Auffret KH Matthews MJ Humphrey HNE Stevens GM Eccleston 2010 Characterisation of freeze-dried wafers and solvent evaporated films as potential drug delivery systems to mucosal surfaces Int J Pharm. 389 24 31 20083177 10.1016/j.ijpharm.2010.01.008 1:CAS:528:DC%2BC3cXivVOlur8%3D
18. HL Lai 2003 Abu'Khalil A, Craig DQM. The preparation and characterisation of drug-loaded alginate and chitosan sponges Int J Pharm. 251 175 81 12527187 10.1016/S0378-5173(02)00590-2 1:CAS:528:DC%2BD3sXis1WgtQ%3D%3D (Pubitemid 36071472)
19. S Karki T Friscic L Fabian PR Laity GM Day W Jones 2009 Improving Mechanical Properties of Crystalline Solids by Cocrystal Formation: New Compressible Forms of Paracetamol Adv Mater. 21 3905 9 10.1002/adma.200900533 1:CAS:528:DC%2BD1MXhtlOqu7rN
20. JM Fachaux AM Guyothermann JC Guyot P Conflant M Drache S Veesler R Boistelle 1995 Pure Paracetamol for Direct Compression.1. Development of Sintered-Like Crystals of Paracetamol Powder Technol. 82 123 8 10.1016/0032-5910(94)02919-F 1:CAS:528:DyaK2MXjvF2ktr8%3D
21. SR Levis PB Deasy 2001 Pharmaceutical applications of size reduced grades of surfactant co-processed microcrystalline cellulose Int J Pharm. 230 25 33 11672953 10.1016/S0378-5173(01)00843-2 1:CAS:528:DC%2BD3MXnslSmsLw%3D (Pubitemid 32973856)
22. GF Palmieri S Michelini P Di Martino S Martelli 2000 Polymers with pH-dependent solubility: possibility of use in the formulation of gastroresistant and controlled-release matrix tablets Drug Dev Ind Pharm. 26 837 45 10900540 10.1081/DDC-100101307 1:CAS:528:DC%2BD3cXks12ju7c%3D (Pubitemid 30451823)
23. GF Palmieri G Bonacucina P Di Martino S Martelli 2001 Spray-drying as a method for microparticulate controlled release systems preparation: advantages and limits. I. Water-soluble drugs Drug Dev Ind Pharm. 27 195 204 11291199 10.1081/DDC-100000237 1:CAS:528:DC%2BD3MXksVOgsrc%3D (Pubitemid 32244941)
24. JH Hu KP Johnston RO Williams 2004 Nanoparticle engineering processes for enhancing the dissolution rates of poorly water soluble drugs Drug Dev Ind Pharm. 30 233 45 15109023 10.1081/DDC-120030422 (Pubitemid 38451748)
25. AHL Chow HHY Tong P Chattopadhyay BY Shekunov 2007 Particle engineering for pulmonary drug delivery Pharm Res. 24 411 37 17245651 10.1007/s11095-006- 9174-3 1:CAS:528:DC%2BD2sXhslWju7Y%3D (Pubitemid 46295160)
26. JS Liu 2006 Physical characterization of pharmaceutical formulations in frozen and freeze-dried solid states: techniques and applications in freeze-drying development Pharm Dev Technol. 11 3 28 16544906 10.1080/10837450500463729 1:CAS:528:DC%2BD28XisVaru7o%3D
27. S Talegaonkar AY Khan RK Khar FJ Ahmad ZI Khan 2007 Development and characterization of paracetamol complexes with hydroxypropyl-beta-cyclodextrin Iran J Pharm Res. 6 95 9 1:CAS:528:DC%2BD2sXhtFGksLbL (Pubitemid 350142086)
28. AN Paruta AS Irani 1965 Dielectric solubility profiles in dioxane-water mixtures for several antipyrectic drugs J Pharm Sci. 54 1334 8 5881231 10.1002/jps.2600540922 1:CAS:528:DyaF2MXkslSrur0%3D
29. S Prakongpan T Nagai 1984 Pharmaceutical Interactions in Dosage Forms and Processing.45. Solubility of Acetaminophen in Cosolvents. Chem Pharm Bull. 32 340 3 1:CAS:528:DyaL2cXhsVCqs74%3D
30. RA Granberg AC Rasmuson 2000 Solubility of paracetamol in binary and ternary mixtures of water plus acetone plus toluene J Chem Eng Data. 45 478 83 10.1021/je990272l 1:CAS:528:DC%2BD3cXisFans78%3D
31. Dyadin YA, Bondaryuk IV, Zhurko FV. Clathrate hydrates at high pressures. In: Atwood JL, Davies JED, MacNicol DD, editors. Inclusion compounds. V.5. Oxford: Oxford University Press; 1991. p. 214-75.
32. AI Ancharov AY Manakov NA Mezentsev BP Tolochko MA Sheromov VM Tsukanov 2001 New station at the 4th beamline of the VEPP-3 storage ring Nucl Instrum Methods Phys Res Sect A-Accel Spectrom Dect Assoc Equip. 470 80 3 10.1016/S0168-9002(01)01029-4 1:CAS:528:DC%2BD3MXmsFentLY%3D (Pubitemid 32798415)
33. Hammersley AP. "Fit2D Programm, 1987-2003", European Synchrotron Research Facility.
34. Rodriguez-Carvajal J. FULLPROF: A program for rietveld refinement and pattern matching analysis. Abstracts of the Satellite Meeting on Powder Diffraction of the XV Congress of the IUCr. Toulouse, France, 1990. p. 127.
35. B Rupp 1988 XLAT-a microcomputer program for the refinement of cell constants Scripta Metallurgica. 22 1 10.1016/S0036-9748(88)80294-1
36. JT Fell JM Newton 1970 Determination of tablet strength by the diametral-compression test J Pharm Sci. 5 688 91 10.1002/jps.2600590523
37. J Malsam A Aksan 2010 Hydrogen bonding and compartmentalization of water in supercooled and frozen aqueous acetone solutions J Phys Chem B. 114 4238 45 20210291 10.1021/jp904381d 1:CAS:528:DC%2BC3cXivV2murs%3D
38. Allan DR, Clark SJ, Ibberson RM, Parsons S, Pulham CR, Sawyer L. The influence of pressure and temperature on the crystal structure of acetone. Chem Commun. 1999;751-2. (Pubitemid 29184722)
39. ML Peterson D McIlroy P Shaw JP Mustonen M Oliveira O Almarsson 2003 Crystallization and transformation of acetaminophen trihydrate Cryst Growth Des. 3 761 5 10.1021/cg0340603 1:CAS:528:DC%2BD3sXlvVGls7o%3D (Pubitemid 37162287)
40. J Baldyga D Kubicki BY Shekunov KB Smith 2010 Mixing effects on particle formation in supercritical fluids Chem Eng Res Des. 88 1131 41 10.1016/j.cherd.2010.02.016 1:CAS:528:DC%2BC3cXht1eisbzP
41. LM Shi CC Sun 2010 Transforming powder mechanical properties by core/shell structure: compressible sand J Pharm Sci. 99 4458 62 20845444 10.1002/jps.22172 1:CAS:528:DC%2BC3cXhtFGqt77O
42. Hüttenrauch R, Fricke S, Zielke P. Mechanical activation of pharmaceutical systems. Pharm Res. 1985;302-6.