Recent advances in co-amorphous drug formulations

Advanced Drug Delivery Reviews

Volumn 100, Issue , 2016, Pages 116-125

  Dengale, Swapnil Jayant ^a   Grohganz, Holger ^b   Rades, Thomas ^b   Löbmann, Korbinian ^b  

^a MANIPAL COLLEGE OF PHARMACEUTICAL SCIENCES   (India)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Co amorphous; Increased dissolution; Molecular interactions; Poorly soluble drugs; Solid dispersion

Indexed keywords

BIOCHEMISTRY; DISPERSIONS; MICROCRYSTALS; MOLECULAR INTERACTIONS; MOLECULAR WEIGHT; STABILIZATION;

LOW MOLECULAR WEIGHT; ORAL BIOAVAILABILITIES; PHARMACEUTICAL FIELDS; POORLY SOLUBLE DRUGS; POORLY WATER-SOLUBLE DRUGS; SCIENTIFIC PUBLICATIONS; SOLID DISPERSION; STABILIZATION TECHNIQUES;

DISSOLUTION;

ACICLOVIR; ATORVASTATIN; CARBAMAZEPINE; CIMETIDINE; CITRIC ACID; CURCUMIN; DIFLUNISAL; FUROSEMIDE; GLIPIZIDE; INDOMETACIN; LURASIDONE; NAPROXEN; PARACETAMOL; PIROXICAM; POLYMER; RANITIDINE; REPAGLINIDE; RITONAVIR; SIMVASTATIN; DRUG;

DISPERSION; DISSOLUTION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; MOLECULAR INTERACTION; MOLECULAR WEIGHT; PRIORITY JOURNAL; REVIEW; BIOAVAILABILITY; MEDICINAL CHEMISTRY; SOLUBILITY;

BIOLOGICAL AVAILABILITY; CHEMISTRY, PHARMACEUTICAL; DRUG COMPOUNDING; PHARMACEUTICAL PREPARATIONS; SOLUBILITY;

EID: 84955574492     PISSN: 0169409X     EISSN: 18728294     Source Type: Journal    
DOI: 10.1016/j.addr.2015.12.009     Document Type: Review

References (80)

1. Aaltonen J., Rades T. Towards physico-relevant dissolution testing: the importance of solid-state analysis in dissolution. Dissolut. Technol. 2009, 16:47-54.
2. Hancock B.C., Zografi G. Characteristics and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci. 1997, 86:1-12.
3. Chiou W.L., Riegelman S. Pharmaceutical applications of solid dispersion systems. J. Pharm. Sci. 1971, 60:1281-1302.
4. Laitinen R., Priemel P.A., Surwase S., Graeser K., Strachan C.J., Grohganz H., Rades T. Theoretical considerations in developing amorphous solid dispersions. Amorphous Solid Dispersions 2014, 35-90. Springer, New York. N. Shah, H. Sandhu, D.S. Choi, H. Chokshi, A.W. Malick (Eds.).
5. Vaka S.R.K., Bommana M.M., Desai D., Djordjevic J., Phuapradit W., Shah N. Excipients for amorphous solid dispersions. Amorphous Solid Dispersions 2014, 123-161. Springer, New York. N. Shah, H. Sandhu, D.S. Choi, H. Chokshi, A.W. Malick (Eds.).
6. Van den Mooter G. The use of amorphous solid dispersions: a formulation strategy to overcome poor solubility and dissolution rate. Drug Discovery Today: Technologies 2012, 9:e79-e85.
7. Marsac P.J., Shamblin S.L., Taylor L.S. Theoretical and practical approaches for prediction of drug-polymer miscibility and solubility. Pharm. Res. 2006, 23:2417-2426.
8. Leuner C., Dressman J. Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 2000, 50:47-60.
9. Hancock B.C., Shamblin S.L., Zografi G. Molecular mobility of amorphous pharmaceutical solids below their glass transition temperatures. Pharm. Res. 1995, 12:799-806.
10. Janssens S., Van den Mooter G. Review: physical chemistry of solid dispersions. J. Pharm. Pharmacol. 2009, 61:1571-1586.
11. Lu Q., Zografi G. Phase behavior of binary and ternary amorphous mixtures containing indomethacin, citric acid, and PVP. Pharm. Res. 1998, 15:1202-1206.
12. Serajuddin A.T.M. Solid dispersion of poorly water-soluble drugs: early promises, subsequent problems, and recent breakthroughs. J. Pharm. Sci. 1999, 88:1058-1066.
13. Vasconcelos T., Sarmento B., Costa P. Solid dispersions as strategy to improve oral bioavailability of poor water soluble drugs. Drug Discov. Today 2007, 12:1068-1075.
14. Brown C., DiNunzio J., Eglesia M., Forster S., Lamm M., Lowinger M., Marsac P., McKelvey C., Meyer R., Schenck L., Terife G., Troup G., Smith-Goettler B., Starbuck C. Hot-melt extrusion for solid dispersions: composition and design considerations. Amorphous Solid Dispersions 2014, 197-230. Springer, New York. N. Shah, H. Sandhu, D.S. Choi, H. Chokshi, A.W. Malick (Eds.).
15. Choudhari Y., Hoefer H., Libanati C., Monsuur F., McCarthy W. Mesoporous silica drug delivery systems. Amorphous Solid Dispersions 2014, 665-693. Springer, New York. N. Shah, H. Sandhu, D.S. Choi, H. Chokshi, A.W. Malick (Eds.).
16. Wang F., Hui H., Barnes T.J., Barnett C., Prestidge C.A. Oxidized mesoporous silicon microparticles for improved oral delivery of poorly soluble drugs. Mol. Pharm. 2010, 7:227-236.
17. Song S.W., Hidajat K., Kawi S. Functionalized SBA-15 materials as carriers for controlled drug delivery: influence of surface properties on matrix-drug interactions. Langmuir 2005, 21:9568-9575.
18. Qian K.K., Bogner R.H. Application of mesoporous silicon dioxide and silicate in oral amorphous drug delivery system. J. Pharm. Sci. 2011, 101:444-463.
19. Prestidge C.A., Barnes T.J., Lau C.-H., Barnett C., Loni A., Canham L. Mesoporous silicon: a platform for the delivery of therapeutics. Expert Opin. Drug Deliv. 2007, 4:101-110.
20. Laitinen R., Löbmann K., Strachan C.J., Grohganz H., Rades T. Emerging trends in the stabilization of amorphous drugs. Int. J. Pharm. 2013, 453:65-79.
21. Löbmann K., Jensen K.T., Laitinen R., Rades T., Strachan C.J., Grohganz H. Stabilized amorphous solid dispersions with small molecule excipients. Amorphous Solid Dispersions 2014, 613-636. Springer, New York. N. Shah, H. Sandhu, D.S. Choi, H. Chokshi, A.W. Malick (Eds.).
22. 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. 2009, 71:47-54.
23. Bates S., Zografi G., Engers D., Morris K., Crowley K., Newman A. Analysis of amorphous and nanocrystalline solids from their X-ray diffraction patterns. Pharm. Res. 2006, 23:2333-2349.
24. Rades T., Gordon K.C., Graeser K. Molecular structure, properties, and states of matter. Remington - The Science and Practise of Pharmacy 2013, 541-570. Pharmaceutical Press, London, United Kingdom. L.V. Allen (Ed.).
25. Craig D.Q.M., Royall P.G., Kett V.L., Hopton M.L. The relevance of the amorphous state to pharmaceutical dosage forms: glassy drugs and freeze dried systems. Int. J. Pharm. 1999, 179:179-207.
26. Sandhu H., Shah N., Chokshi H., Malick A.W. Overview of amorphous solid dispersion technologies. Amorphous Solid Dispersions 2014, 91-122. Springer, New York. N. Shah, H. Sandhu, D.S. Choi, H. Chokshi, A.W. Malick (Eds.).
27. Fukuoka E., Makita M., Yamamura S. Glassy state of pharmaceuticals. III.: thermal properties and stability of glassy pharmaceuticals and their binary glass systems. Chem. Pharm. Bull. 1989, 37:1047-1050.
28. Martínez L.M., Videa M., López-Silva G.A., de los Reyes C.A., Cruz-Angeles J., González N. Stabilization of amorphous paracetamol based systems using traditional and novel strategies. Int. J. Pharm. 2014, 477:294-305.
29. Johari G.P., Kim S., Shanker R.M. Dielectric study of equimolar acetaminophen-aspirin, acetaminophen-quinidine, and benzoic acid-progesterone molecular alloys in the glass and ultraviscous states and their relevance to solubility and stability. J. Pharm. Sci. 2010, 99:1358-1374.
30. Hoppu P., Jouppila K., Rantanen J., Schantz S., Juppo A.M. Characterisation of blends of paracetamol and citric acid. J. Pharm. Pharmacol. 2007, 59:373-381.
31. Hoppu P., Hietala S., Schantz S., Juppo A.M. Rheology and molecular mobility of amorphous blends of citric acid and paracetamol. Eur. J. Pharm. Biopharm. 2009, 71:55-63.
32. 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. 2009, 98:1862-1870.
33. Shimada Y., Goto S., Uchiro H., Hirabayashi H., Yamaguchi K., Hirota K., Terada H. Features of heat-induced amorphous complex between indomethacin and lidocaine. Colloids Surf. B: Biointerfaces 2013, 102:590-596.
34. Shimada Y., Goto S., Uchiro H., Hirota K., Terada H. Characteristics of amorphous complex formed between indomethacin and lidocaine hydrochloride. Colloids Surf. B: Biointerfaces 2013, 105:98-105.
35. Pajula K., Wittoek L., Lehto V.-P., Ketolainen J., Korhonen O. Phase separation in coamorphous systems: in silico prediction and the experimental challenge of detection. Mol. Pharm. 2014, 11:2271-2279.
36. Löbmann 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. 2011, 8:1919-1928.
37. Löbmann K., Laitinen R., Grohganz H., Strachan C., Rades T., Gordon K.C. A theoretical and spectroscopic study of co-amorphous naproxen and indomethacin. Int. J. Pharm. 2013, 453:80-87.
38. Yamamura S., Gotoh H., Sakamoto Y., Momose Y. Physicochemical properties of amorphous salt of cimetidine and diflunisal system. Int. J. Pharm. 2002, 241:213-221.
39. Yamamura S., Gotoh H., Sakamoto Y., Momose Y. Physicochemical properties of amorphous precipitates of cimetidine-indomethacin binary system. Eur. J. Pharm. Biopharm. 2000, 49:259-265.
40. Shayanfar A., Jouyban A. Drug-drug coamorphous systems: characterization and physicochemical properties of Coamorphous atorvastatin with carvedilol and glibenclamide. J. Pharm. Innov. 2013, 8:218-228.
41. 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. 2012, 422:160-169.
42. Tantishaiyakul V., Suknuntha K., Vao-Soongnern V. Characterization of cimetidine-piroxicam coprecipitate interaction using experimental studies and molecular dynamic simulations. AAPS PharmSciTech 2010, 11:952-958.
43. Gao Y., Liao J., Qi X., Zhang J. Coamorphous repaglinide-saccharin with enhanced dissolution. Int. J. Pharm. 2013, 450:290-295.
44. Suresh K., Mannava M.K.C., Nangia A. A novel curcumin-artemisin coamorphous solid: physical properties and pharmacokinetic profile. RCS Adv. 2014, 4:58357-58361.
45. Dengale S.J., Ranjan O.P., Hussen S.S., Krishna B.S.M., Musmade P.B., Gautham Shenoy G., Bhat K. Preparation and characterization of co-amorphous ritonavir-indomethacin systems by solvent evaporation technique: improved dissolution behavior and physical stability without evidence of intermolecular interactions. Eur. J. Pharm. Sci. 2014, 62:57-64.
46. Dengale S.J., Hussen S.S., Krishna B.S.M., Musmade P.B., Gautham Shenoy G., Bhat K. Fabrication, solid state characterization and bioavailability assessment of stable binary amorphous phases of ritonavir with quercetin. Eur. J. Pharm. Biopharm. 2015, 89:329-338.
47. Qian S., Heng W., Wei Y., Zhang J., Gao Y. Coamorphous lurasidone hydrochloride-saccharin with charge-assisted hydrogen bonding interaction shows improved physical stability and enhanced dissolution with pH-independent solubility behavior. Cryst. Growth Des. 2015, 15:2920-2928.
48. Descamps M., Willart J.F., Dudognon E., Caron V. Transformation of pharmaceutical compounds upon milling and comilling: the role of Tg. J. Pharm. Sci. 2007, 96:1398-1407.
49. Hu Y., Gniado K., Erxleben A., McArdle P. Mechanochemical reaction of sulfathiazole with carboxylic acids: formation of a cocrystal, a salt, and coamorphous solids. Cryst. Growth Des. 2014, 14:803-813.
50. 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. 2012, 81:159-169.
51. Löbmann K., Grohganz H., Laitinen R., Strachan C., Rades T. Amino acids as co-amorphous stabilizers for poorly water soluble drugs - part 1: preparation, stability and dissolution enhancement. Eur. J. Pharm. Biopharm. 2013, 85:873-881.
52. Jensen K.T., Löbmann K., Rades T., Grohganz H. Improving co-amorphous drug formulations by the addition of the highly water soluble amino acid proline. Pharmaceutics 2014, 6:416-435.
53. Löbmann K., Laitinen R., Strachan C., Rades T., Grohganz H. Amino acids as co-amorphous stabilizers for poorly water-soluble drugs - part 2: molecular interactions. Eur. J. Pharm. Biopharm. 2013, 85:882-888.
54. Laitinen R., Löbmann K., Grohganz H., Strachan C., Rades T. Amino acids as co-amorphous excipients for simvastatin and glibenclamide: physical properties and stability. Mol. Pharm. 2014, 11:2381-2389.
55. Heikkinen A.T., DeClerck L., Löbmann K., Grohganz H., Rades T., Laitinen R. Dissolution properties of co-amorphous drug-amino acid formulations in buffer and biorelevant media. Pharmazie 2015, 70:452-457.
56. Jensen K.T., Larsen F.H., Cornett C., Löbmann K., Grohganz H., Rades T. Formation mechanism of coamorphous drug-amino acid mixtures. Mol. Pharm. 2015, 12:2484-2492.
57. Allesø 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 2009, 136:45-53.
58. Lenz E., Jensen K.T., Blaabjerg L.I., Knop K., Grohganz H., Löbmann K., Rades T., Kleinebudde P. Solid-state properties and dissolution behaviour of tablets containing co-amorphous indomethacin-arginine. Eur. J. Pharm. Biopharm. 2015, 96:44-52.
59. Shamblin S.L., Taylor L.S., Zografi G. Mixing behavior of colyophylized binary systems. J. Pharm. Sci. 1998, 87:694-701.
60. Hoppu P., Grönroos A., Schantz S., Juppo A.M. New processing technique for viscous amorphous materials and characterisation of their stickiness and deformability. Eur. J. Pharm. Biopharm. 2009, 72:183-188.
61. Hoppu P., Virpioja J., Schantz S., Juppo A.M. Characterization of ultrasound extrudated and cut citric acid/paracetamol blends. J. Pharm. Sci. 2009, 98:2140-2148.
62. Wickström H., Palo M., Rijckaert K., Kolakovic R., Nyman J.O., Määttänen A., Ihalainen P., Peltonen J., Genina N., de Beer T., Löbmann K., Rades T., Sandler N. Improvement of dissolution rate of indomethacin by inkjet printing. Eur. J. Pharm. Sci. 2015, 75:91-100.
63. Marsac P., Li T., Taylor L. Estimation of drug-polymer miscibility and solubility in amorphous solid dispersions using experimentally determined interaction parameters. Pharm. Res. 2009, 26:139-151.
64. Baird J.A., Taylor L.S. Evaluation of amorphous solid dispersion properties using thermal analysis techniques. Adv. Drug Deliv. Rev. 2012, 64:396-421.
65. Kawakami K. Modification of physicochemical characteristics of active pharmaceutical ingredients and application of supersaturatable dosage forms for improving bioavailability of poorly absorbed drugs. Adv. Drug Deliv. Rev. 2012, 64:480-495.
66. Yu L. Amorphous pharmaceutical solids: preparation, characterization and stabilization. Adv. Drug Deliv. Rev. 2001, 48:27-42.
67. van Drooge D.J., Hinrichs W.L.J., Visser M.R., Frijlink H.W. Characterization of the molecular distribution of drugs in glassy solid dispersions at the nano-meter scale, using differential scanning calorimetry and gravimetric water vapour sorption techniques. Int. J. Pharm. 2006, 310:220-229.
68. Knopp M.M., Tajber L., Tian Y., Olesen N.E., Jones D.S., Kozyra A., Löbmann K., Paluch K., Brennan C.M., Holm R., Healy A.M., Andrews G.P., Rades T. Comparative study of different methods for the prediction of drug-polymer solubility. Mol. Pharm. 2015, 12:3408-3419.
69. Shamblin S.L., Tang X., Chang L., Hancock B.C., Pikal M.J. Characterization of the time scales of molecular motion in pharmaceutically important glasses. J. Phys. Chem. B 1999, 103:4113-4121.
70. Jensen K.T., Blaabjerg L.I., Lenz E., Bohr A., Grohganz H., Kleinebudde P., Rades T., Löbmann K. Preparation and characterization of spray-dried co-amorphous drug-amino acid salts. J. Pharm. Pharmacol. 2015, 10.1111/jphp.12458.
71. Teja A., Musmade P.B., Khade A.B., Dengale S.J. Simultaneous improvement of solubility and permeability by fabricating binary glassy materials of Talinolol with Naringin: Solid state characterization, in-vivo in-situ evaluation. Eur. J. Pharm. Sci. 2015, 78:234-244.
72. Brostow W., Chiu R., Kalogeras I.M., Vassilikou-Dova A. Prediction of glass transition temperatures: binary blends and copolymers. Mater. Lett. 2008, 62:3152-3155.
73. Moynihan C.T. Correlation between the width of the glass transition region and the temperature dependence of the viscosity of high-Tg glasses. J. Am. Ceram. Soc. 1993, 76:1081-1087.
74. Painter P.C., Graf J.F., Coleman M.M. Effect of hydrogen bonding on the enthalpy of mixing and the composition dependence of the glass transition temperature in polymer blends. Macromolecules 1991, 24:5630-5638.
75. Lu X., Weiss R.A. Relationship between the glass transition temperature and the interaction parameter of miscible binary polymer blends. Macromolecules 1992, 25:3242-3246.
76. Alonzo D., Zhang G.Z., Zhou D., Gao Y., Taylor L. Understanding the behavior of amorphous pharmaceutical systems during dissolution. Pharm. Res. 2010, 27:608-618.
77. Lipinski C.A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2000, 44:235-249.
78. Wagner D., Spahn-Langguth H., Hanafy A., Koggel A., Langguth P. Intestinal drug efflux: formulation and food effects. Adv. Drug Deliv. Rev. 2001, 50(Suppl. 1):S13-S31.
79. Akbuga J., Gürsoy A., Yetimoĝlu F. Preparation and properties of tablets prepared from furosemide-PVP solid dispersion systems. Drug Dev. Ind. Pharm. 1988, 14:2091-2108.
80. Owusu-Ababio G., Ebube N.K., Reams R., Habib M. Comparative dissolution studies for mefenamic acid-polyethylene glycol solid dispersion systems and tablets. Pharm. Dev. Technol. 1998, 3:405-412.