Novel pharmaceutical salts of albendazole
Albendazole (ABZ) is a class II safe and effective antihelmintic drug in the benzimidazole group according to the BCS (Biopharmaceutics Classification System) with low solubility (9 mg L-1) and high permeability (logP 2.54). Novel salts and salt hydrates of ABZ are reported with benzene and p-toluen...
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| Format: | Article |
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Royal Society of Chemistry (RSC)
2018
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| Online Access: | http://hdl.handle.net/1721.1/119185 |
| _version_ | 1811080924955148288 |
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| author | Bolla, Geetha Nangia, Ashwini |
| author2 | Massachusetts Institute of Technology. Department of Chemical Engineering |
| author_facet | Massachusetts Institute of Technology. Department of Chemical Engineering Bolla, Geetha Nangia, Ashwini |
| author_sort | Bolla, Geetha |
| collection | MIT |
| description | Albendazole (ABZ) is a class II safe and effective antihelmintic drug in the benzimidazole group according to the BCS (Biopharmaceutics Classification System) with low solubility (9 mg L-1) and high permeability (logP 2.54). Novel salts and salt hydrates of ABZ are reported with benzene and p-toluene sulfonic acid (BSA, PTSA), as well as carboxylic acids such as oxalic acid (OA), maleic acid (MLE), l-tartaric acid (LTA), 2,6-dihydroxybenzoic acid (2,6-DHBA), and 2,4,6-trihydroxybenzoic acid (2,4,6-THBA). The products ABZ-BSA, ABZ-BSA-H, ABZ-PTSA, ABZ-PTSA-H, ABZ-OA-H and ABZ-2,6-DHBA were confirmed by single crystal X-ray diffraction. In the hydrate structures (designated as -H), the water molecule acts as a bridge in the hydrogen bonding network. The salt formation of ABZ-MLE, ABZ-LTA, and ABZ-2,4,6-THBA was confirmed by 15N ss-NMR based on the chemical shift change of ca. 50 ppm. The sulfonate salt hydrates exhibit 2D isostructurality, and position disorder in the thiopropyl group in the drug crystal structure was not observed in the salts. Crystal lattice energies were calculated for the MLE, LTA, and 2,4,6-THBA complexes of ABZ to confirm the molecular salt formation. The cocrystals of ABZ with the hydroxybenzene carboxylic acids are novel salts in the benzimidazole drugs class. |
| first_indexed | 2024-09-23T11:39:01Z |
| format | Article |
| id | mit-1721.1/119185 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2024-09-23T11:39:01Z |
| publishDate | 2018 |
| publisher | Royal Society of Chemistry (RSC) |
| record_format | dspace |
| spelling | mit-1721.1/1191852022-09-27T20:59:40Z Novel pharmaceutical salts of albendazole Bolla, Geetha Nangia, Ashwini Massachusetts Institute of Technology. Department of Chemical Engineering Bolla, Geetha Albendazole (ABZ) is a class II safe and effective antihelmintic drug in the benzimidazole group according to the BCS (Biopharmaceutics Classification System) with low solubility (9 mg L-1) and high permeability (logP 2.54). Novel salts and salt hydrates of ABZ are reported with benzene and p-toluene sulfonic acid (BSA, PTSA), as well as carboxylic acids such as oxalic acid (OA), maleic acid (MLE), l-tartaric acid (LTA), 2,6-dihydroxybenzoic acid (2,6-DHBA), and 2,4,6-trihydroxybenzoic acid (2,4,6-THBA). The products ABZ-BSA, ABZ-BSA-H, ABZ-PTSA, ABZ-PTSA-H, ABZ-OA-H and ABZ-2,6-DHBA were confirmed by single crystal X-ray diffraction. In the hydrate structures (designated as -H), the water molecule acts as a bridge in the hydrogen bonding network. The salt formation of ABZ-MLE, ABZ-LTA, and ABZ-2,4,6-THBA was confirmed by 15N ss-NMR based on the chemical shift change of ca. 50 ppm. The sulfonate salt hydrates exhibit 2D isostructurality, and position disorder in the thiopropyl group in the drug crystal structure was not observed in the salts. Crystal lattice energies were calculated for the MLE, LTA, and 2,4,6-THBA complexes of ABZ to confirm the molecular salt formation. The cocrystals of ABZ with the hydroxybenzene carboxylic acids are novel salts in the benzimidazole drugs class. 2018-11-19T15:57:06Z 2018-11-19T15:57:06Z 2018-11 2018-08 2018-11-14T14:16:32Z Article http://purl.org/eprint/type/JournalArticle 1466-8033 http://hdl.handle.net/1721.1/119185 Bolla, Geetha and Ashwini Nangia. “Novel Pharmaceutical Salts of Albendazole.” CrystEngComm 20, 41 (2018): 6394–6405 © 2018 The Royal Society of Chemistry http://dx.doi.org/10.1039/c8ce01311j CrystEngComm Creative Commons Attribution-NonCommercial 3.0 Unported https://creativecommons.org/licenses/by-nc/3.0/ application/pdf Royal Society of Chemistry (RSC) Royal Society of Chemistry |
| spellingShingle | Bolla, Geetha Nangia, Ashwini Novel pharmaceutical salts of albendazole |
| title | Novel pharmaceutical salts of albendazole |
| title_full | Novel pharmaceutical salts of albendazole |
| title_fullStr | Novel pharmaceutical salts of albendazole |
| title_full_unstemmed | Novel pharmaceutical salts of albendazole |
| title_short | Novel pharmaceutical salts of albendazole |
| title_sort | novel pharmaceutical salts of albendazole |
| url | http://hdl.handle.net/1721.1/119185 |
| work_keys_str_mv | AT bollageetha novelpharmaceuticalsaltsofalbendazole AT nangiaashwini novelpharmaceuticalsaltsofalbendazole |