Issue 13, 2019

Stanozolol–aromatic carboxylic acid crystalline complexes: flexible tautomeric/ionization states and supramolecular synthons

Abstract

Stanozolol (STAN) is an androgenic and anabolic steroid medication used for the treatment of anemia, osteoporosis, and hereditary angioedema. This weakly basic compound possesses two energy-equivalent tautomers. These tautomeric forms and neutral/cationic states of STAN allow the presence of diverse intermolecular interactions in its crystalline complexes. Two salts and five cocrystals of STAN have been reported with acidic guest molecules. Here, five novel crystalline complexes of STAN with benzoic acid derivatives, 2,6-dihydroxybenzoic acid (DBA), 2,5-dihydroxybenzoic acid (DHA), 1,2-benzenedicarboxylic acid (PHA), and gallic acid (GA), were successfully prepared. The molecular states of STAN and supramolecular synthons in these solid forms were disclosed via the solved single crystal structures and the 13C solid state NMR spectra. Additionally, all the new anhydrous crystalline phases demonstrated favourable thermal stability and physical stability against hydration.

Graphical abstract: Stanozolol–aromatic carboxylic acid crystalline complexes: flexible tautomeric/ionization states and supramolecular synthons

Supplementary files

Article information

Article type
Paper
Submitted
27 Aug. 2018
Accepted
30 Nov. 2018
First published
03 Dec. 2018

CrystEngComm, 2019,21, 2144-2153

Stanozolol–aromatic carboxylic acid crystalline complexes: flexible tautomeric/ionization states and supramolecular synthons

X. Wang, M. Kong, D. Li, J. Fang, Z. Deng and H. Zhang, CrystEngComm, 2019, 21, 2144 DOI: 10.1039/C8CE01439F

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