Characterization of two new degradation products of atorvastatin calcium formed upon treatment with strong acids
| Autor: | Markus Luber, Franz Bracher, Jürgen Kraus, Peter Mayer, Monika Klimt |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
crystal structure
cyclization Hydrochloric acid 01 natural sciences Medicinal chemistry Full Research Paper lcsh:QD241-441 Residue (chemistry) chemistry.chemical_compound lcsh:Organic chemistry degradation products fragmentation Moiety lcsh:Science Pyrrole chemistry.chemical_classification 010405 organic chemistry 010401 analytical chemistry Organic Chemistry Sulfuric acid atorvastatin Nuclear magnetic resonance spectroscopy 0104 chemical sciences Chemistry chemistry stress test lcsh:Q Isopropyl Lactone |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 15, Iss 1, Pp 2085-2091 (2019) |
| ISSN: | 1860-5397 |
| Popis: | Atorvastatin calcium (Lipitor®, Sortis®) is a well-established cholesterol synthesis enzyme (CSE) inhibitor commonly used in the therapy of hypercholesterolemia. This drug is known to be sensitive to acid treatment, but only little data has been published on the structures of the degradation products. Here we report the identification of two novel degradation products of atorvastatin, which are formed only under drastic acidic conditions. While treatment with conc. sulfuric acid led to a loss of the carboxanilide residue (accompanied by an expectable lactonization/dehydration process in the side chain), treatment with conc. aqueous hydrochloric acid gave a complex, bridged molecule under C–C-bond formation of the lactone moiety with the pyrrole, migration of the isopropyl group and loss of the carboxanilide residue. The novel degradation products were characterized by NMR spectroscopy, HRMS data and X-ray crystal structure analysis. |
| Databáze: | OpenAIRE |
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