Crystal engineering of the composition of pharmaceutical phases. 3. Primary amide supramolecular heterosynthons and their role in the design of pharmaceutical co-crystals

Abstract

A Cambridge Structural Database study of supramolecular synthons involving primary amides reveals that 84% form amide-amide dimers, whereas 14% form catemers in the absence of other competing hydrogen bond donors and/or acceptors. However in the presence of chemically different but complementary functional groups,

The Co‐Crystal Approach to Improve the Exposure of a Water‐Insoluble Compound: AMG 517 Sorbic Acid Co‐Crystal Characterization and Pharmacokinetics

“…Zaworotko et al described in a recent article the successful use of the CSD (Cambridge Structural Database), a database containing structural data based on X-ray and neutron diffraction data, to search for cocrystal formers for Carbamazepine. 25,26 How could co-crystals be of interest to the pharmaceutical industry? In the early 1990s there was a change in the in vitro biology screening paradigm in the pharmaceutical industry going from aqueous based manual screening to high throughput screening starting with the compound solubilized in DMSO.…”

Novel drug–drug cocrystals of carbamazepine with para-aminosalicylic acid: screening, crystal structures and comparative study of carbamazepine cocrystal formation thermodynamics

“…In this case, the crystal structure of [CBZ + PASA + H 2 O] shows the same packing arrangement as that of the carbamazepine cocrystal monohydrate with PABA in a 2 : 1 molar ratio (CSD refcode XAQREN). 32 The crystal structure of [CBZ + PASA + H 2 O] forms an 8-membered supramolecular discrete unit consisting of four carbamazepine molecules, two para-aminosalicylic acid molecules and two water molecules (Fig. 6b).…”

Covalent-Assisted Supramolecular Synthesis: Masking of Amides in Co-Crystal Synthesis using Benzophenone Derivatives

“…1 A prime example of such functionality can be found in the carboxylic acid···pyridine hydrogen bond. The robustness of the functionality has been illustrated by the consistent hydrogen bonding pattern that occurs between the COOH···N bond of carboxylic acid groups and the pyridine nitrogen atom of isonicotinic acid hydrazide (isoniazid).…”