Effect of cryogrinding on chemical stability of the sparingly water-soluble drug furosemide

Pharmaceutical Research

Volumn 28, Issue 12, 2011, Pages 3220-3236

  Adrjanowicz, Karolina ^a   Kaminski, Kamil ^a   Grzybowska, Katarzyna ^a   Hawelek, Lukasz ^a   Paluch, Marian ^a   Gruszka, Irena ^a   Zakowiecki, Daniel ^b   Sawicki, Wieslaw ^c   Lepek, Przemyslaw ^c   Kamysz, Wojciech ^c   Guzik, Lukasz ^c  

^a UNIVERSITY OF SILESIA   (Poland)

^b Pharmaceutical Works Polpharma SA   (Poland)

^c MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

amorphous pharmaceuticals; cryogenic grinding; furosemide; mechnochemical reactions; solid state amorphization

Indexed keywords

4 CHLORO 5 SULFAMOYLANTHRANILIC ACID; ANTHRANILIC ACID DERIVATIVE; EXCIPIENT; FUROSEMIDE; INULIN; LIQUID NITROGEN; POVIDONE; UNCLASSIFIED DRUG;

ARTICLE; CRYOGRINDING; CRYSTAL STRUCTURE; DRUG DECOMPOSITION; DRUG DEGRADATION; DRUG PURITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; GRINDING; PRIORITY JOURNAL;

CHEMISTRY, PHARMACEUTICAL; COLD TEMPERATURE; DIURETICS; DRUG STABILITY; EQUIPMENT DESIGN; EXCIPIENTS; FUROSEMIDE; MAGNETIC RESONANCE SPECTROSCOPY; PARTICLE SIZE; SOLUBILITY; WATER; X-RAY DIFFRACTION;

EID: 83555173484     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-011-0496-4     Document Type: Article

References (42)

1. GL Amidon H Lennernäs VP Shah JR Crison 1995 A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability Pharm Res 12 413 20 7617530 10.1023/A:1016212804288 1:CAS:528:DyaK2MXksVGqur8%3D
2. JC Chaumeil 1998 Micronisation: a method of improving the bioavailability of poorlysolubledrugs Methods Find Exp Clin Pharmacol 20 211 5 9646283 1:CAS:528:DyaK1cXktV2mtrs%3D (Pubitemid 28255411)
3. AR Sheth S Bates FX Muller DJW Grant 2004 Polymorphism in piroxicam Cryst Growth Des 4 1091 8 10.1021/cg049876y 1:CAS:528:DC%2BD2cXntFWitLc%3D (Pubitemid 39531985)
4. N Chieng Z Zujovic G Bowmaker T Rades D Saville 2006 Effect of milling conditions on the solid-state conversion of ranitidine hydrochloride form 1 Int J Pharm 327 36 44 16949221 10.1016/j.ijpharm.2006.07.032 1:CAS:528: DC%2BD28XhtFKhsb%2FP (Pubitemid 44667333)
5. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. Solubility advantage of amorphous pharmaceuticals: II. Application of quantitative thermodynamic relationships for prediction of solubility enhancement in structurally diverse insoluble pharmaceuticals. Pharm Res. 2010; doi: 10.1007/s11095-010-0269-5.
6. M Yoshioka BC Hancock G Zografi 1994 Crystallization of indomethacin from the amorphous state below and above its glass transition temperature J Pharm Sci 83 1700 5 7891297 10.1002/jps.2600831211 1:CAS:528:DyaK2cXms1entrY%3D
7. SL Shamblin BC Hancock MJ Pikal 2006 Coupling between chemical reactivity and structural relaxation in pharmaceutical glasses Pharm Res 23 2254 68 16941232 10.1007/s11095-006-9080-8 1:CAS:528:DC%2BD28XhtVeqsbjP (Pubitemid 44515010)
8. 3Sn during heavy mechanical impact J Less-Common Met 168 183 93 10.1016/0022-5088(91)90300- S 1:CAS:528:DyaK3MXitFajsLc%3D
9. S Desprez M Decamps 2006 Transformation of glassy indomethacin induced by ball-milling J Non-Cryst Solids 353 4480 5 10.1016/j.jnoncrysol.2006.02.130 (Pubitemid 44646965)
10. JF Willart V Caron R Lefort F Dandède D Prèvost M Decamps 2004 Athermal character of the solid state amorphization of lactose induced by ball milling Solid State Commun 132 693 6 10.1016/j.ssc.2004.09.007 1:CAS:528:DC%2BD2cXptl2qtLk%3D
11. M Decamps JF Willart E Dudognon V Caron 2007 Transformation of pharmaceutical compounds upon milling and comilling: the role of Tg J Pharm Sci 96 1398 407 10.1002/jps.20939 (Pubitemid 46797497)
12. E Fukuoka M Markita S Yamamura 1986 Some physicochemical properties of glassy indomethacin Chem Pharm Bull 34 4314 21 3829165 1:CAS:528: DyaL2sXitlWktQ%3D%3D (Pubitemid 17201167)
13. KJ Crowley G Zografi 2002 Cryogenic grinding of indomethacin polymorphs and solvates: assessment of amorphous phase formation and amorphous phase physical stability J Pharm Sci 91 492 507 11835208 10.1002/jps.10028 1:CAS:528:DC%2BD38XhsVSms7g%3D (Pubitemid 34139812)
14. NQ Lam PR Okamoto M Li 1997 Disorder-induced amorphization J Nucl Mat 251 89 97 10.1016/S0022-3115(97)00257-2 1:CAS:528:DyaK2sXnvFSntLo%3D (Pubitemid 127377991)
15. HJ Fech 1992 Defect-induced melting and solid-state amorphization Nature 356 133 5 10.1038/356133a0
16. Decamps M, Willart JF, Aumelas A. The Glass Transition of Driven Molecular Materials. Complex Systems 5th International Workshop on Complex Systems. 2008;53:61.
17. TP Shakhtshneider F Danède F Capet JF Willart M Decamps SA Myz, et al. 2007 Grinding of drugs with pharmaceutical excipients at cryogenic temperatures, Part 1 J Therm Anal Calorim 89 699 707 10.1007/s10973-006-7958-7 1:CAS:528:DC%2BD2sXpvVCisbw%3D (Pubitemid 47351761)
18. AR Sheth JW Lubach EJ Munson FX Muller DJW Grant 2005 Mechanochromism of piroxicam accompanied by intermolecular proton transfer probed by spectroscopic methods and solid-phase changes J Am Chem Soc 127 6641 51 15869285 10.1021/ja045823t 1:CAS:528:DC%2BD2MXjtFeitLY%3D (Pubitemid 40667527)
19. KA Greaser CJ Strachan JE Patterson KC Gordon T Rades 2008 Physicochemical properties and stability of two differently prepared amorphous forms of simvastatin Cryst Growth Des 8 128 35 10.1021/cg700913m
20. www.drugbank.ca.
21. H Ogata Y Kawatsu Y Maruyama K Machida T Haga 1985 Bioavailability and diuretic effect of furosemide during long-term treatment of chronic respiratory failure Eur J Clin Pharm 28 53 9 10.1007/BF00635708 1:STN:280: DyaL2M7nvFOjug%3D%3D (Pubitemid 15126528)
22. H Bundgaard T Norgaard NM Nielsen 1988 Photodegradation and hydrolysis of furosemide and furosemide esters in aqueous solutions Int J Pharm 2 217 24 10.1016/0378-5173(88)90178-0 (Pubitemid 18092109)
23. DMS Valladao LCS De Oliveira J Zuanon Netto M Ionashiro 1996 Thermal decomposition of some diuretic agents J Therm Anal 46 1291 9 10.1007/BF01979243 1:CAS:528:DyaK28XkvVCjsL8%3D (Pubitemid 126793613)
24. RM Amin Kreaz EY Abu-Eida I Eros M Kata 1999 Freeze-dried complexes of furosemide with β-cyclodextrin dervatives J Incl Phenom Macrocyclic Chem 34 39 48 10.1023/A:1008032324924
25. AG Ghanekar VG Gupta CW Gibbs Jr 1978 Stability of furosemide in aqueous systems J Pharm Sci 67 808 11 660463 10.1002/jps.2600670621 1:CAS:528: DyaE1cXkvVSitL4%3D (Pubitemid 8355242)
26. V Iannuccelli G Coppi E Leo F Fontana MT Bernabei 2000 PVP solid dispersion for the controlled pelease of furosemide from a floating multiple-unit system Drug Dev Ind Pharm 26 595 603 10826107 10.1081/DDC- 100101274 1:CAS:528:DC%2BD3cXjt1CjsL0%3D (Pubitemid 30317065)
27. S-C Shin I-J Oh Y-B Lee H-K Choi J-S Choi 1998 Enhanced dissolution of furosemide by coprecipitating or cogrinding with crospovidone Int J Pharm 175 17 24 10.1016/S0378-5173(98)00260-9 1:CAS:528:DyaK1cXmslSqurY%3D (Pubitemid 28487012)
28. MW Villiers RL Tiedt 1996 An analysis of fine grinding and aggregation of poorly soluble drug powders in a vibrating ball mill Pharmazie 51 564 7 1:CAS:528:DyaK28XkvFequ7w%3D
29. Kaminski K, Adrjanowicz K, Wojnarowska K, Grzybowska K, Hawelek L, Paluch M, et al. Molecular dynamics of the cryomilled base and hydrochloride Ziprasidones by means of dielectric spectroscopy. J Pharm Sci. 2011; doi: 10.1002/jps.22479.
30. JE Cruz GJ Yakatan 1979 Kinetics and mechanism of hydrolysis of furosemide Int J Pharm 2 275 81 10.1016/0378-5173(79)90034-6 1:CAS:528:DyaE1MXltFOis7Y%3D (Pubitemid 9161628)
31. IA Al-Omar RM Al-Ashban AH Shah 2009 Toxicity studies on 4-chloro-5-sulfamoylanthranilic acid the degradation product of a loop diuretic furosemide Res J Pharmac. 3 63 77
32. DE Moore V Sithipitak 1983 Photolytic degradation of frusemide J Pharm Pharmacol 35 489 93 6137532 10.1111/j.2042-7158.1983.tb04816.x 1:CAS:528:DyaL3sXlvVWgt74%3D (Pubitemid 13075878)
33. Adrjanowicz K, Grzybowska K, Kaminski K, Hawelek L, Paluch M, Zakowiecki D. Complex studies on physical and chemical stability in liquid and glassy states of Telmisartan (TEL). Solubility advantages given by cryomilled and quenched material. Phil. Mag. in press.
34. Bühler V. Polyvinylpyrrolidone excipients for pharmaceuticals. Berlin: Springer-Verlag; 2005.
35. C Doherty P York 1987 Evidence for solid- and liquid-state interactions in a furosemide-polyvinylpyrrolidone solid dispersion J Pharm Sci 76 731 7 11002811 10.1002/jps.2600760912 1:CAS:528:DyaL1cXhtFWitQ%3D%3D (Pubitemid 18026984)
36. C Doherty P York 1989 Accelerated stability of an x-ray amorphous furosemide-polyvinylpyrrolidone solid dispersion Drug Dev Ind Pharm 15 1969 87 10.3109/03639048909052513 1:CAS:528:DyaL1MXlt1Skt7Y%3D (Pubitemid 19194678)
37. E Spamer DG Muller PL Wessels JP Venter 2002 Characterization of the complexes of furosemide with 2-hydroxypropyl-β-cyclodextrin and sulfobutyl ether-7-β-cyclodextrin Eur J Pharm Sci 16 247 53 12208454 10.1016/S0928-0987(02)00107-0 1:CAS:528:DC%2BD38Xms1ynsrs%3D
38. H Beyers SF Malan JG van der Waat MM de Villiers 2000 Structure-solubility relationship and thermal decomposition of furosemide Drug Dev Ind Pharm 36 10 1077 83 10.1081/DDC-100100271
39. PG McCormick FH Froes 1998 The fundamentals of mechanochemical processing J Miner Met Mater Soc 50 11 61 5 10.1007/s11837-998-0290-x 1:CAS:528: DyaK1cXnslyjtb0%3D
40. Heinickie G. Tribichemistry. Berlin: Akademic-Verlag; 1984.
41. F Delogu L Schiffini G Cocco 2001 The invariant laws of the amorphization processes by mechanical alloying. I Experimental findings Phil Mag A 81 8 1917 37 10.1080/01418610010019107 1:CAS:528:DC%2BD3MXmt1Wqsbc%3D
42. J Andrade-Gamboa FC Gennari P Arneodo Larochette C Neyertz M Ahlers JL Pelegrina 2007 Stability of Cu-Zn phases under low energy ball milling Mat Sci Eng A 447 324 31 10.1016/j.msea.2006.10.134 (Pubitemid 46075953)