Article ; Online: Polymorphism in sulfadimidine/4-aminosalicylic acid cocrystals: solid-state characterization and physicochemical properties.
Journal of pharmaceutical sciences
2015 Volume 104, Issue 4, Page(s) 1385–1398
Abstract: Polymorphism of crystalline drugs is a common phenomenon. However, the number of reported polymorphic cocrystals is very limited. In this work, the synthesis and solid-state characterization of a polymorphic cocrystal composed of sulfadimidine (SD) and 4- ...
| Abstract | Polymorphism of crystalline drugs is a common phenomenon. However, the number of reported polymorphic cocrystals is very limited. In this work, the synthesis and solid-state characterization of a polymorphic cocrystal composed of sulfadimidine (SD) and 4-aminosalicylic acid (4-ASA) is reported for the first time. By liquid-assisted milling, the SD:4-ASA 1:1 form I cocrystal, the structure of which has been previously reported, was formed. By spray drying, a new polymorphic form (form II) of the SD:4-ASA 1:1 cocrystal was discovered which could also be obtained by solvent evaporation from ethanol and acetone. Structure determination of the form II cocrystal was calculated using high-resolution X-ray powder diffraction. The solubility of the SD:4-ASA 1:1 cocrystal was dependent on the pH and predicted by a model established for a two amphoteric component cocrystal. The form I cocrystal was found to be thermodynamically more stable in aqueous solution than form II, which showed transformation to form I. Dissolution studies revealed that the dissolution rate of SD from both cocrystals was enhanced when compared with a physical equimolar mixture and pure SD. © 2015 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 104:1385-1398, 2015. |
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| MeSH term(s) | Acetone/chemistry ; Aminosalicylic Acid/chemistry ; Anti-Bacterial Agents/chemistry ; Anti-Inflammatory Agents/chemistry ; Chemistry, Pharmaceutical ; Crystallization ; Crystallography, X-Ray ; Drug Combinations ; Drug Stability ; Ethanol/chemistry ; Hydrogen-Ion Concentration ; Kinetics ; Magnetic Resonance Spectroscopy ; Models, Chemical ; Models, Molecular ; Powder Diffraction ; Solubility ; Solvents/chemistry ; Spectroscopy, Fourier Transform Infrared ; Sulfamethazine/chemistry ; Technology, Pharmaceutical/methods ; Temperature | |||||
| Chemical Substances | Anti-Bacterial Agents ; Anti-Inflammatory Agents ; Drug Combinations ; Solvents ; Acetone (1364PS73AF) ; Ethanol (3K9958V90M) ; Sulfamethazine (48U51W007F) ; Aminosalicylic Acid (5B2658E0N2) | |||||
| Language | English | |||||
| Publishing date | 2015-04 | |||||
| Publishing country | United States | |||||
| Document type | Comparative Study ; Journal Article ; Research Support, Non-U.S. Gov't | |||||
| ZDB-ID | 3151-3 | |||||
| ISSN | 1520-6017 ; 0022-3549 | |||||
| ISSN (online) | 1520-6017 | |||||
| ISSN | 0022-3549 | |||||
| DOI | 10.1002/jps.24345 | |||||
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| Database | MEDical Literature Analysis and Retrieval System OnLINE |
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