Identification of the Secondary Degradates of L-648,548 in an Animal Health Formulation
| Autor: | Qingxi Wang, John M. Ballard, J.-S.K. Shim, Joan S. Murphy, Pierre DeMontigny, Arthur J. Faulkner, John D. Stong |
|---|---|
| Rok vydání: | 1996 |
| Předmět: |
chemistry.chemical_classification
Insecticides Ivermectin Base (chemistry) Animal health Photodissociation Pharmaceutical Science medicine.disease Tautomer chemistry.chemical_compound Drug Stability chemistry medicine Organic chemistry Phenol Dehydration Drug Contamination Avermectin E1cB-elimination reaction |
| Zdroj: | Journal of Pharmaceutical Sciences. 85:446-450 |
| ISSN: | 0022-3549 |
| DOI: | 10.1021/js950483i |
| Popis: | L-648,548 is a semisynthetic analog of avermectin. During stability investigations of this compound in an animal health formulation, two new degradates were discovered. These degradates (L-648,548 phenol and its 8,9-Z isomer) were identified as the reaction products of 5-oxo-L-648,548 formed by oxidation of L-648,548. Addition of base to the reaction medium containing 5-oxo-L-648,548 was found to catalyze the formation of L-648,548 phenol via a postulated dehydration by an E1cb elimination followed by the rapid tautomerization of the C5 carbonyl. Photolysis of L-648,548 phenol with visible light (including ambient laboratory lighting) was found to readily produce 8,9-Z-L-648,548 phenol. This transformation was confirmed to be exclusively a photoinduced process. |
| Databáze: | OpenAIRE |
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