Relationships between structural and thermal properties of anhydrous and solvated crystalline forms of brodimoprim

Mino R. Caira, Giampiero Bettinetti, Milena Sorrenti, Laura Catenacci

Research output: Contribution to journalArticle

Abstract

The isolation and physicochemical characterization of four crystalline modifications of brodimoprim (5-[(4-bromo-3,5-dimethoxyphenyl)methyl]-2,4- pyrimidinediamine, hereinafter BMP), a structural analog of trimethoprim (TMP), are reported. These phases include an unsolvated form of BMP, a hemihydrate (BMP·0.5H2O), a 1:1 solvate containing isopropanol (BMP·C3H7OH(iso)), and a hemichloroformate (BMP·0.5CHC13). Unsolvated BMP was isolated both by recrystallization from a range of common solvents as well as by thermal decomposition of the above solvates and no evidence for polymorphism was found. PXRD data indicated that the three solvates crystallize in different arrangements. Data from thermal analysis (thermogravimetry (TGA), hot stage microscopy (HSM), differential scanning calorimetry (DSC)) of the solvates containing water and iso-propanol were interpreted on the basis of their single-crystal X-ray structures which revealed that the modes of solvent inclusion in BMP·0.5H2O and BMP·C3H 7OH(iso) may be described as 'isolated site' and 'lattice channel' type inclusions, respectively.

Original languageEnglish
Pages (from-to)996-1007
Number of pages12
JournalJournal of Pharmaceutical Sciences
Volume96
Issue number5
DOIs
Publication statusPublished - May 2007

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Structural properties
Thermodynamic properties
Hot Temperature
Thermogravimetry
Crystalline materials
1-Propanol
Trimethoprim
2-Propanol
Differential Scanning Calorimetry
Polymorphism
Thermoanalysis
Thermogravimetric analysis
Microscopy
Differential scanning calorimetry
Microscopic examination
Pyrolysis
X-Rays
Single crystals
X rays
Water

Keywords

  • Brodimoprim
  • Drug solvates
  • Thermal analysis
  • X-ray diffraction

ASJC Scopus subject areas

  • Molecular Medicine
  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Pharmacology

Cite this

Relationships between structural and thermal properties of anhydrous and solvated crystalline forms of brodimoprim. / Caira, Mino R.; Bettinetti, Giampiero; Sorrenti, Milena; Catenacci, Laura.

In: Journal of Pharmaceutical Sciences, Vol. 96, No. 5, 05.2007, p. 996-1007.

Research output: Contribution to journalArticle

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