Amorphous drugs and dosage forms

Journal of Drug Delivery Science and Technology

Volumn 23, Issue 4, 2013, Pages 403-408

  Grohganz, H ^a   Lobmann K ^a,b   Priemel, P ^a,b   Tarp Jensen, K ^a   Graeser, K ^c   Strachan, C ^b,d   Rades, T ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF OTAGO   (New Zealand)

^c F HOFFMANN LA ROCHE LTD   (Switzerland)

^d UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Amorphous; Class solution; Co amorphous; Solid dispersion; Spatial separation

Indexed keywords

ARGININE; CARBAMAZEPINE; CIMETIDINE; EXCIPIENT; GLIPIZIDE; GRISEOFULVIN; INDOMETACIN; NAPROXEN; NIFEDIPINE; PHENYLALANINE; POLYMER; RANITIDINE; SIMVASTATIN; TRYPTOPHAN; TYROSINE;

AMORPHOUS DRUG DOSAGE FORM; CRYSTALLIZATION; DENSITY FUNCTIONAL THEORY; DISPERSION; DRUG COATING; DRUG DOSAGE FORM; DRUG FORMULATION; DRUG MIXTURE; DRUG SOLUBILITY; DRUG STABILITY; DRUG TRANSFORMATION; ELECTROSTATIC PRECIPITATION; ENERGY; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; GLASS TRANSITION TEMPERATURE; MICROPRECIPITATED BULK POWDER TECHNOLOGY; MOISTURE; MOLECULAR INTERACTION; PRECIPITATION; RAMAN SPECTROMETRY; REVIEW; SEPARATION TECHNIQUE; SPATIAL SEPARATION;

EID: 84881580992     PISSN: 17732247     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1773-2247(13)50057-8     Document Type: Review

References (54)

1. Hancock B. C., Zografi G. - Characteristics and significance of the amorphous state in pharmaceutical systems. - J. Pharm. Sci., 86(1), 1-12, 1997.
2. Hancock B. C., Parks M. - What is the true solubility advantage for amorphous pharmaceuticals? - Pharm. Res., 17(4), 397-404, 2000. (Pubitemid 30395293)
3. Murdande S. B., Pikal M. J., Shanker R. M., Bogner R. H. - Aqueous solubility of crystalline and amorphous drugs: challenges in measurement. - Pharm. Dev. Technol., 16(3), 187-200, 2011.
4. Newman A., Knipp G., Zografi G. - Assessing the performance of amorphous solid dispersions. - J. Pharm. Sci., 101(4), 1355-1377, 2012.
5. Hancock B., Shamblin S., Zografi G. - Molecular mobility of amorphous pharmaceutical solids below their glass transition temperatures. - Pharm. Res., 12(6), 799-806, 1995.
6. Miyazaki T., Yoshioka S., Aso Y., Kawanishi T. - Crystallization rate of amorphous nifedipine analogues unrelated to the glass transition temperature. - Int. J. Pharm., 336(1), 191-195, 2007. (Pubitemid 46551570)
7. Xiang T.-X., Anderson B. D. - Molecular dynamics simulation of amorphous indomethacin. - Mol. Pharm., 10(1), 102-114, 2012.
8. Hancock B. C., Shamblin S. L. - Molecular mobility of amorphous pharmaceuticals determined using differential scanning calorimetry. - Thermochimica Acta, 380(2), 95-107, 2001. (Pubitemid 33096427)
9. Mao C., Chamarthy S. P., Pinal R. - Calorimetric study and modeling of molecular mobility in amorphous organic pharmaceutical compounds using a modified Adam-Gibbs approach. - The Journal of Physical Chemistry B, 111(46), 13243-13252, 2007. (Pubitemid 350254031)
10. Bhugra C., Pikal M. J. - Role of thermodynamic, molecular, and kinetic factors in crystallization from the amorphous state. - J. Pharm. Sci., 97(4), 1329-1349, 2008.
11. Graeser K. A., Patterson J. E., Zeitler J. A., Gordon K. C., Rades T. - Correlating thermodynamic and kinetic parameters with amorphous stability. - Eur. J. Pharm. Sci., 37(3-4), 492-498, 2009.
12. Baird J. A., Van Eerdenbrugh B., Taylor L. S. - Aclassification system to assess the crystallization tendency of organic molecules from undercooled melts. - J. Pharm. Sci., 99(9), 3787-3806, 2010.
13. Graeser K. A., Patterson J. E., Rades T. - Applying thermodynamic and kinetic parameters to predict the physical stability of two differently prepared amorphous forms of simvastatin. - Curr. Drug Deliv., 6(4), 374-382, 2009.
14. Karmwar P., Graeser K., Gordon K. C., Strachan C. J., Rades T. - Investigation of properties and recrystallisation behaviour of amorphous indomethacin samples prepared by different methods. - Int. J. Pharm., 417(1-2), 94-100, 2011.
15. Shah N., Sandhu H., Phuapradit W., Pinal R., Iyer R., Albano A., Chatterji A., Anand S., Choi D. S., Tang K., Tian H., Chokshi H., Singhal D., Malick W. - Development of novel microprecipitated bulk powder (MBP) technology for manufacturing stable amorphous formulations of poorly soluble drugs. - Int. J. Pharm., 438(1-2), 53-60, 2012.
16. Graeser K. A., Strachan C. J., Patterson J. E., Gordon K. C., Rades T. - Physicochemical properties and stability of two differently prepared amorphous forms of simvastatin. - Cryst. Growth Des., 8, 128-135, 2008.
17. Patterson J. E., James M. B., Forster A. H., Lancaster R. W., Butler J. M., Rades T. - The influence of thermal and mechanical preparative techniques on the amorphous state of four poorly soluble compounds. - J. Pharm. Sci., 94, 1998-2012, 2005. (Pubitemid 41551483)
18. Savolainen M., Heinz A., Strachan C., Gordon K. C., Yliruusi J., Rades T., Sandler N. - Screening fordifferences in the amorphous state of indomethacin using multivariate visualization. - Eur. J. Pharm. Sci., 30(2), 113-123, 2007. (Pubitemid 46149278)
19. Karmwar P., Boetker J. P., Graeser K. A., Strachan C. J., Rantanen J., Rades T. - Investigations on the effect of different cooling rates on the stability of amorphous indomethacin. - Eur. J. Pharm. Sci., 44(3), 341-350, 2011.
20. Karmwar P., Graeser K., Gordon K. C., Strachan C. J., Rades T. - Effect of different preparation methods on the dissolution behaviour of amorphous indomethacin. - Eur. J. Pharm. Biopharm., 80(2), 459-464, 2012.
21. Singh A., Worku Z. A., Van den Mooter G. - Oral formulation strategies to improve solubility of poorly water-soluble drugs. - Expert Opin. Drug Deliv., 8(10), 1361-1378, 2011.
22. Vasconcelos T., Sarmento B., Costa P. - Solid dispersions as strategy to improve oral bioavailability of poor water soluble drugs. - Drug Discov. Today, 12(23-24), 1068-1075, 2007. (Pubitemid 350186132)
23. Leuner C., Dressman J. - Improving drug solubility for oral delivery using solid dispersions. - Eur. J. Pharm. Biopharm., 50(1), 47-60, 2000. (Pubitemid 30326688)
24. Patterson J. E., James M. B., Forster A. H., Lancaster R. W., Butler J. M., Rades T. - Preparation of glass solutions of three poorly water soluble drugs by spray drying, melt extrusion and ball milling. - Int. J. Pharm., 336(1), 22-34, 2007. (Pubitemid 46551551)
25. Tobyn M., Brown J., Dennis A. B., Fakes M., Gao Q., Gamble J., Khimyak Y. Z., McGeorge G., Patel C., Sinclair W., Timmins P., Yin S. - Amorphous drug-PVP dispersions: Application of theoretical, thermal and spectroscopic analytical techniques to the study of a molecule with intermolecular bonds in both the crystalline and pure amorphous state. - J. Pharm. Sci., 98(9), 3456-3468, 2009.
26. Taylor L. S., Zografi G. - Spectroscopic characterization of interactions between PVP and Indomethacin in amorphous molecular dispersions. - Pharm. Res., 14(12), 1691-1698, 1997. (Pubitemid 28062912)
27. Karavas E., Georgarakis M., Docoslis A., Bikiaris D. - Combining SEM, TEM, and micro-Raman techniques to differentiate between the amorphous molecular level dispersions and nanodispersions of a poorly water-soluble drug within a polymer matrix. - Int. J. Pharm., 340(1-2), 76-83, 2007. (Pubitemid 47044963)
28. Qian F., Huang J., Zhu Q., Haddadin R., Gawel J., Garmise R., Hussain M. - Is a distinctive single Tg a reliable indicator for the homogeneity of amorphous solid dispersion? - Int. J. Pharm., 395(1-2), 232-235, 2010.
29. Rumondor A. F., Wikström H., Van Eerdenbrugh B., Taylor L. - Understanding the tendency of amorphous solid dispersions to undergo amorphous-amorphous phase separation in the presence of absorbed moisture. - AAPS PharmSciTech, 12(4), 1209-1219, 2011.
30. Greenhalgh D. J., Williams A. C., Timmins P., York P. - Solubility parameters as predictors of miscibility in solid dispersions. - J. Pharm. Sci., 88(11), 1182-1190, 1999. (Pubitemid 29526305)
31. Marsac P., Shamblin S., Taylor L. - Theoretical and practical approaches for prediction of drug-polymer miscibility and solubility. - Pharm. Res., 23(10), 2417-2426, 2006. (Pubitemid 44511522)
32. Newman A., Engers D., Bates S., Ivanisevic I., Kelly R. C., Zografi G. - Characterization of amorphous APhPolymer mixtures using X-ray powder diffraction. - J. Pharm. Sci., 97(11), 4840-4856, 2008.
33. Van den Mooter G., Wuyts M., Blaton N., Busson R., Grabet P., Augustijns P., Kinget R. - Physical stabilisation of amorphous ketoconazole in solid dispersions with polyvinylpyrrolidone K25. - Eur. J. Pharm. Sci., 12(3), 261-269, 2001.
34. Janssens S., Van den Mooter G. - Review: physical chemistry of solid dispersions. - J. Pharm. Pharmacol., 61(12), 1571-1586, 2009.
35. Nielsen L. H., Keller S. S., Gordon K. C., Boisen A., Rades T., Mullertz A. - Spatial confinement can lead to increased stability of amorphous indomethacin. - Eur. J. Pharm. Biopharm., 81(2), 418-425, 2012.
36. Andronis V., Yoshioka M., Zografi G. - Effects of sorbed water on the crystallization of indomethacin from the amorphous state. - J. Pharm. Sci., 86(3), 346-351, 1997.
37. Wu T., Sun Y., Li N., de Villiers M. M., Yu L. - Inhibiting surface crystallization of amorphous indomethacin by nanocoating. - Langmuir, 23(9), 5148-5153, 2007. (Pubitemid 46732007)
38. Zhu L., Jona J., Nagapudi K., Wu T. - Fast surface crystallization of amorphous griseofulvin below Tg. - Pharm. Res., 27(8), 1558-1567, 2010.
39. Zhu L., Wong L., Yu L. - Surface-enhanced crystallization of amorphous nifedipine. - Mol. Pharm., 5(6), 921-926, 2008.
40. Puri V., Dantuluri A. K., Bansal A. K. - Barrier coated drug layered particles for enhanced performance of amorphous solid dispersion dosage form. - J. Pharm. Sci., 101(1), 342-353, 2012.
41. Ahuja N., Katare O. P., Singh B. - Studies on dissolution enhancement and mathematical modeling of drug release of a poorly water-soluble drug using water-soluble carriers. - Eur. J. Pharm. Biopharm., 65(1), 26-38, 2007. (Pubitemid 44827692)
42. Descamps M., Willart J. F., Dudognon E., Caron V. - Transformation of pharmaceutical compounds upon milling and comilling: the role of Tg. - J. Pharm. Sci., 96(5), 1398-1407, 2007. (Pubitemid 46797497)
43. Masuda T., Yoshihashi Y., Yonemochi E., Fujii K., Uekusa H., Terada K. - Cocrystallization and amorphization induced by drug-excipient interaction improves the physical properties of acyclovir. - Int. J. Pharm., 422(1-2), 160-169, 2012.
44. Hoppu P., Jouppila K., Rantanen J., Schantz S., Juppo A. M. - Characterisation of blends of paracetamol and citric acid. - J. Pharm. Pharmacol., 59(3), 373-381, 2007. (Pubitemid 47050901)
45. Schantz S., Hoppu P., Juppo A. M. - A solid-state NMR study of phase structure, molecular interactions, and mobility in blends of citric acid and paracetamol. - J. Pharm. Sci., 98(5), 1862-1870, 2009.
46. Chieng N., Aaltonen J., Saville D., Rades T. - Physical characterization and stability of amorphous indomethacin and ranitidine hydrochloride binary systems prepared by mechanical activation. - Eur. J. Pharm. Biopharm., 71(1), 47-54, 2009.
47. Alleso M., Chieng N., Rehder S., Rantanen J., Rades T., Aaltonen J. - Enhanced dissolution rate and synchronized release of drugs in binary systems through formulation: Amorphous naproxen-cimetidine mixtures prepared by mechanical activation. - J. Control. Release, 136(1), 45-53, 2009.
48. Lobmann K., Laitinen R., Grohganz H., Gordon K. C., Strachan C., Rades T. - Coamorphous drug systems: enhanced physical stability and dissolution rate of indomethacin and naproxen. - Mol. Pharm., 8(5), 1919-1928, 2011.
49. Löbmann K., Strachan C., Grohganz H., Rades T., Korhonen O., Laitinen R. - Co-amorphous simvastatin and glipizide combinations show improved physical stability without evidence of intermolecular interactions. - Eur. J. Pharm. Biopharm., 81(1), 159-169, 2012.
50. Löbmann K., Laitinen R., Grohganz H., Strachan C., Rades T., Gordon K. C. - A theoretical and spectroscopic study of coamorphous naproxen and indomethacin. - Int. J. Pharm., doi: 10.1016/j.ijpharm.2012.05.016(0), 2012.
51. Lobmann K., Grohganz H., Laitinen R., Strachan C. J., Rades T. - Amino acids as co-amorphous stabilisers for poorly water soluble drugs - Part 1: Preparation, stability and dissolution enhancement. - Eur. J. Pharm. Biopharm., under revision 2013.
52. Lobmann K., Laitinen R., Strachan C. J., Rades T., Grohganz H. - Amino acids as co-amorphous stabilisers for poorly water soluble drugs - Part 2: Molecular Interactions. - Eur. J. Pharm. Biopharm., under revision 2013.
53. Rowlinson S. W., Kiefer J. R., Prusakiewicz J. J., Pawlitz J. L., Kozak K. R., Kalgutkar A. S., Stallings W. C., Kurumbail R. G., Marnett L. J. - A novel mechanism of cyclooxygenase-2 inhibition involving interactions with Ser-530 and Tyr-385. - J. Biol. Chem., 278(46), 45763-45769, 2003. (Pubitemid 37432720)
54. Yang Y.-C., Huang C.-S., Kuo C.-C. - Lidocaine, carbamazepine, and imipramine have partially overlapping binding sites and additive inhibitory effect on neuronal Na+ channels. - Anesthesiology, 113(1), 160-174 2010.