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94659-47-9Amoxicillin EP Impurity C
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| Catalogue No.: | VL1970004 |
|---|---|
| CAS No.: | 94659-47-9 |
| Mol. Formula: | C16H19N3O5S |
| Mol. Weight: | 365.4 g/mol |
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Additional information on CAS 94659-47-9
Parent drug
AmoxicillinIUPAC Name
(4S)-2-[5-(4-Hydroxyphenyl)-3,6-dioxopiperazin-2-yl]-5,5-dimethylthiazolidine-4-carboxylic acidPharmacopoeial Synonyms
Amoxicillin Related Compound C; Amoxicillin DiketopiperazineOther Synonyms
Amoxicillin Piperazine-2,5-dione; 2-[5-(4-hydroxyphenyl)-3,6-dioxopiperazin-2-yl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acidSmiles
OC1=CC=C(C2NC(C(C3SC(C)(C)[C@]([H])(C(O)=O)N3)NC2=O)=O)C=C1InChI
InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-14(25-16)10-13(22)17-9(12(21)18-10)7-3-5-8(20)6-4-7/h3-6,9-11,14,19-20H,1-2H3,(H,17,22)(H,18,21)(H,23,24)Description
Amoxicillin EP Impurity C, also designated Amoxicillin Related Compound C or amoxicillin diketopiperazine, is a defined β-lactam degradation product formed by intramolecular cyclization of amoxicillin during storage, processing, or stressed hydrolytic conditions. With CAS 94659-47-9, formula C16H19N3O5S, and molecular weight 365.4 g/mol, it retains the thiazolidine and aromatic side chain while losing the native open-chain amino functionality. Its characterization typically requires orthogonal HPLC with UV detection, LC-MS/MS for exact-mass confirmation, and, where needed, NMR for structural assignment. Regulatory assessment focuses on degradant profiling rather than ICH M7 genotoxic impurity classification.References
Valvo, L., et al. Development of a Simple Liquid Chromatographic Method with UV and Mass Spectrometric Detection for the Separation of Substances Related to Amoxicillin Sodium.†Journal of Chromatography A, vol. 797, no. 1-2, Feb. 1998, pp. 311–16, https://doi.org/10.1016/s0021-9673(97)00952-7 Zhu, Yongxin, et al. Evaluation of Liquid Chromatography Methods for the Separation of Ampicillin and Its Related Substances.†Journal of Pharmaceutical and Biomedical Analysis, vol. 14, no. 5, Mar. 1996Request a Quote
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