Pharmaceutical salt formation guided by phase diagrams

Industrial and Engineering Chemistry Research

Volumn 49, Issue 24, 2010, Pages 12503-12512

  Lam, Ka W ^a   Xu, Jinjie ^a   Ng, Ka M ^a   Wibowo, Christianto ^b   Lin, Ge ^c   Luo, Kathy Q ^d  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b ClearWaterBay Technology Inc   (United States)

^c CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^d Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

CACO-2 CELLS; DISODIUM SALT; IONIZABLE GROUPS; PHARMACEUTICAL COMPOUNDS; POORLY WATER-SOLUBLE DRUGS; SALT FORMATION; SOLID LIQUID EQUILIBRIUM;

BIOCHEMISTRY; SOLUBILITY;

PHASE DIAGRAMS;

EID: 78650147283     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie902080k     Document Type: Article

References (49)

1. Serajuddin, A. T. M. Salt Formation to Improve Drug Solubility Adv. Drug Delivery Rev. 2007, 59, 603
2. Berge, S. M.; Bighley, L. D.; Monkhouse, D. C. Pharmaceutical Salts J. Pharm. Sci. 1977, 66, 1
3. Stahl, P. H.; Wermuth, C. G., Eds. Handbook of Pharmaceutical Salts; VHAC, Wiley-VCH: New York, 2002.
4. Paulekuhn, G. S.; Dressman, J. B.; Saal, C. Trends in Active Pharmaceutical Ingredient Salt Selection based on Analysis of the Orange Book Database J. Med. Chem. 2007, 50, 6665
5. Gwak, H. S.; Choi, J. S.; Choi, H. K. Enhanced Bioavailability of Piroxicam via Salt Formation with Ethanolamines Int. J. Pharm. 2005, 297, 156
6. Banerjee, R.; Bhatt, P. M.; Ravindra, N. V.; Desiraju, G. R. Saccharin Salts of Active Pharmaceutical Ingredients, Their Crystal Structures, and Increased Water Solubilities Cryst. Growth Des. 2005, 5, 2299
7. Bani-Jaber, A.; Hamdan, I.; Al-Khalidi, B. Sodium Mefenamate as a Solution for the Formulation and Dissolution Problems of Mefenamic Acid Chem. Pharm. Bull. 2007, 55, 1136
8. Sádaba, B.; Campanero, M. A.; Muñoz-Juarez, M. J.; Gil-Aldea, I.; García-Quetglas, E.; Esteras, A.; Azanza, J. R. A Comparative Study of the Pharmacokinetics of Ibuprofen Arginate versus Dexibuprofen in Healthy Volunteers Eur. J. Clin. Pharmacol. 2006, 62, 849
9. Furesz, S. Blood Levels Following Oral Administration of Different Preparations of Novobiocin Antibiot. Chemother. 1958, 8, 446
10. Nelson, E.; Knoechel, E. L.; Hamlin, W. E.; Wagner, J. G. Influence of Absorption Rate of Tolbutamide on Rate of Decline of Blood Sugar Levels in Normal Humans J. Pharm. Sci. 1962, 51, 509
11. Rubino, J. T. Soluibilities and Solid State Properties of Sodium Salts of Drugs J. Pharm. Sci. 1989, 78, 485
12. Agharkar, S.; Lindenbaum, S.; Higuchi, T. Enhancement of Solubility of Drug Salts by Hydrophilic Counterions: Properties of Organic Salts of an Antimalarial Drug J. Pharm. Sci. 1976, 65, 747
13. Engel, G. L.; Farid, N. A.; Faul, M. M.; Richardson, L. A.; Winneroski, L. L. Salt Form Selection and Characterization of LY333531 Mesylate Monohydrate Int. J. Pharm. 2000, 198, 239
14. Anderson, B. D.; Conradi, R. A. Predictive Relationships in the Water Solubility of Salts of a Non-Steroidal Anti-Inflammatory Drug J. Pharm. Sci. 1985, 74, 815
15. O'Connor, K. M.; Corrigan, O. I. Preparation and Characterization of a Range of Diclofenac Salts Int. J. Pharm. 2001, 226, 163
16. Maurin, M. B.; Rowe, S. M.; Koval, C. A.; Hussain, M. A. Solubilization of Nicardipine Hydrochloride via Complexation and Salt Formation J. Pharm. Sci. 1994, 83, 1418
17. Fawzi, M. B.; Mahjour, M. Salts/Ion pairs of Non-Steroidal Anti-Inflammatory Drugs in Various Dosage Forms. U.S. Patent 5,373,022.
18. Rafati, H.; Ghassempour, A.; Barzegar-Jalali, M. A. New Solution for a Chronic Problem; Aqueous Enteric Coating J. Pharm. Sci. 2006, 95, 2432
19. Khalil, E.; Najjar, S.; Sallam, A. Aqueous Solubility of Diclofenac Diethylamine in the Presence of Pharmaceutical Additives: A Comparative Study with Diclofenac Sodium Drug Dev. Ind. Pharm. 2000, 26, 375
20. Guthmann, C.; Lipp, R.; Wagner, T.; Kranz, H. Development of a Multiple Unit Pellet Formulation for a Weakly Basic Drug Drug Dev. Ind. Pharm. 2007, 33, 341
21. Badman, A. Controlled Release Oral Drug Delivery System. European Patent, Application Number 05010202.9.
22. Gould, P. L. Salt Selection for Basic Drugs Int. J. Pharm. 1986, 33, 201
23. Remenar, J. F.; MacPhee, J. M.; Larson, B. K.; Tyagi, V. A.; Ho, J. H.; McIlroy, D. A.; Hickey, M. B.; Shaw, P. B.; Almarsson, O. Salt Selection and Simultaneous Polymorphism Assessment via High-Throughput Crystallization: The Case of Sertraline Org. Process Res. Dev. 2003, 7, 990
24. Morris, K. R.; Fakes, M. G.; Thakur, A. B.; Newman, A. W.; Singh, A. K.; Venit, J. J.; Spagnuolo, C. J.; Serajuddin, A. T. M. An Integrated Approach to the Selection of Optimal Salt Form for a New Drug Candidate Int. J. Pharm. 1994, 105, 209
25. Lin, Z.; Zhou, L.; Mahajan, A.; Song, S.; Wang, T.; Ge, Z.; Ellison, D. Real-Time Endpoint Monitoring and Determination for a Pharmaceutical Salt Formation Process with In-Line FT-IR Spectroscopy J. Pharm. Biomed. Anal. 2006, 41, 99
26. 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, 1053
27. Berry, D. A.; Ng, K. M. Synthesis of Reactive Crystallization Processes AIChE J. 1997, 43, 1737
28. MarvinSketch. Available at: http://www.chemaxon.com/marvin/sketch/index. jsp, 2008.
29. Barnett, C. J.; Wilson, T. M.; Kobierski, M. E. A. Practical Synthesis of Multitargeted Antifolate LY231514 Org. Process Res. Dev. 1999, 3, 184
30. Busolli, J.; Diulgheroff, N.; Racz, C. N.; Pirkes, M.; Pontiroli, A.; Villa, M.; Aronhime, J. Crystalline Forms of Pemetrexed Diacid and Processes for the Preparation Thereof. U.S. Patent US 2008/0045711 A1.
31. Chelius, E. C.; Reutzel-Edens, S. M.; den Berghe Snorek, S. V. Crystalline of N -[4-[2-(2-Amino-4,7-dihydro-4oxo-3H-pyrrolo[2,3-D]Pyrimidin-5- yl)ethylbenzoyl]-L-Glutamic Acid and Process Thereof. U.S. Patent US 7,138,521 B2.
32. Diulgheroff, N.; Pirkes, M.; Pontiroli, A.; Villa, M.; Busolli, J.; Casalone, R. Highly Pure Pemetrexed Diacid and Processes for the Preparation Thereof. World Intellectual Property Organization, Int. Bureau, Int. Publication Number WO 2008/021410 A2.
33. Premetrexed Disodium for Injection 100 mg or 500 mg Pemetrexed per Vial, Alimta Product Monograph, 2008.
34. Busolli, J.; Diulgheroff, N.; Pirkes, M.; Pontiroli, A.; Villa, M. Processes for the Preparation of Lyophilized Pharmaceutically Acceptable Salts of Pemetrexed Diacid. U.S. Patent US 2008/0139810 A1.
35. Harjo, B.; Ng, K. M.; Wibowo, C. Development of Amino Acid Crystallization Processes: L-Glutamic Acid Ind. Eng. Chem. Res. 2007, 46, 2814
36. Wibowo, C.; Ng, K. M. Visualization of High-Dimensional Phase Diagrams of Molecular and Ionic Mixtures AIChE J. 2002, 45, 991
37. Pochopin, N. L.; Charman, W. N.; Stella, V. J. Amino Acid Derivatives of Dapsone as Water-Soluble Prodrugs Int. J. Pharm. 1995, 121, 157
38. Pochopin, N. L.; Charman, W. N.; Stella, V. J. Pharmacokinetics of Dapsone and Amino Acid Prodrugs of Dapsone Drug Metab. Dispos. 1994, 22, 770
39. Kulkarni, V. M.; Mishra, D. S. Chemical Drug Delivery System: I Preparation and Evaluation of Prodrugs of Dapsone Indian J. Leprosy 1985, 57, 756
40. Prabhakaran, K.; Harris, E. B.; Kirchhcimer, W. F. A Possible Method for Improving the Efficacy of Dapsone Cell. Mol. Life Sci. 1980, 36, 1350
41. Tsong, T. Y.; Swarbrick, J. Sustained-Release Delivery System, I: Phase Diagram Studies of Dapsone and Selected Derivatives J. Pharm. Sci. 1986, 75, 53
42. Tsong, T. Y.; Swarbrick, J. Sustained-Release Delivery Systems, II: In Vitro Dissolution of 4,4′-sulfonylbisbenzamine (dapsone)-N-dodecanoyl- 4,4′-sulfonylbisbenzamineComelts J. Pharm. Sci. 1986, 75, 264
43. Barthe, L.; Woodley, J.; Houin, G. Gastrointestinal Absorption of Drugs: Methods and Studies Fundam. Clin. Pharmacol. 1999, 13, 154
44. Spernath, A.; Aserin, A.; Ziserman, L.; Danino, D.; Garti, N. Phosphatidylcholine Embedded Microemulsions: Physical Properties and Improved Caco-2 Cell Permeability J. Controlled Release 2007, 119, 279
45. Sambuy, Y.; De Angelis, I.; Ranaldi, G.; Scarino, M. L.; Stammati, A.; Zucco, F. The Caco-2 Cell Line as a Model of the Intestinal Barrier: Influence of Cell and Culture-Related Factors on Caco-2 Cell Functional Characteristics Cell Biol. Toxicol. 2006, 21, 1
46. Artursson, P.; Palm, K.; Luthman, K. Caco-2 Monolayers in Experimental and Theoretical Predictions of Drug Transport Adv. Drug Delivery Rev. 2001, 46, 27
47. Shah, P.; Jogani, V.; Bagchi, T.; Misra, A. Role of Caco-2 Cell Monolayers in Prediction of Intestinal Drug Absorption Biotechnol. Prog. 2006, 22, 186
48. Artursson, P.; Karlsson, J. Correlation between Oral Drug Absorption in Humans and Apparent Drug Permeability Coefficients in Human Intestinal Epithelial (Caco-2) Cell Biochem. Biophys. Res. Commun. 1991, 175, 880
49. Cheng, Y. S.; Lam, K. W.; Ng, K. M.; Wibowo, C. Workflow for Managing Impurities in an Integrated Crystallization Process AIChE J. 2008, 56, 633