Product Number: C041058
English Name: Clindamycin Sulfoxide
English Alias: (2S,4R)-N-((1S,2S)-2-chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfinyl)tetrahydro-2H-pyran-2-yl)propyl)-1-methyl-4-propylpyrrolidine-2-carboxamide
CAS Number: 22431-46-5
Molecular Formula: C₁₈H₃₃ClN₂O₆S
Molecular Weight: 440.98
As a sulfoxide impurity of Clindamycin, this compound has the following advantages:
Well-defined and distinct structure: Retains clindamycin’s pyrrolidine carboxamide, chloropropyl, and pyranose skeletons, with methyl sulfide (-S-CH₃) oxidized to methyl sulfoxide (-S(O)-CH₃). Significant polarity difference from clindamycin enables accurate identification via HPLC and LC-MS as a specific impurity marker;
High stability and traceability: Sulfoxide group (-S(O)-) is stable under neutral conditions. As the major oxidation product of clindamycin sulfide during storage, it directly reflects oxidative deterioration, improving quality tracing accuracy;
High detection sensitivity: Enhanced chromatographic retention from sulfoxide polarity and pyranose hydroxyls, combined with chlorine isotope pattern (³⁵Cl/³⁷Cl, 3:1) and mass response (m/z 441/443 [M+H]⁺), enables trace analysis via LC-MS (ppb level), compatible with lincosamide antibiotic detection systems.
Pharmaceutical quality control: Used as an impurity reference standard to quantify Clindamycin Sulfoxide in APIs and formulations, ensuring residual sulfoxide impurities meet quality standards;
Stability evaluation: Assessing oxidative stability of clindamycin formulations under light/high temperature by monitoring impurity levels to guide storage conditions (e.g., light protection);
Metabolic profiling: Serving as a major oxidative metabolite to trace clindamycin’s in vivo clearance pathways in biological samples (plasma, urine).
Clindamycin, a lincosamide antibiotic for gram-positive infections (e.g., staphylococci), inhibits bacterial protein synthesis. Its sulfide group (-S-CH₃) is prone to oxidation during storage (especially under air/light) to form Clindamycin Sulfoxide. This impurity has significantly lower antibacterial activity and may affect stability, making its control critical for clindamycin quality assurance.
Current research focuses on:
Analytical method validation: Developing UPLC-MS/MS assays with optimized fragment selection (e.g., m/z 126) for simultaneous quantification of impurity and clindamycin, achieving 0.1 ppb detection limits;
Oxidation kinetics: Studying impurity formation under varying oxidant conditions to clarify sulfide oxidation mechanisms (e.g., metal ion catalysis);
Antibacterial activity comparison: Evaluating MIC differences between impurity and clindamycin against S. aureus to establish scientifically based limits;
Formulation stabilization: Incorporating antioxidants (e.g., sulfites) or gas-flushed packaging to minimize sulfoxide formation in clindamycin products.
China
