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Methyl Ester of Nafcilloic Acid

The Methyl Ester of Nafcilloic Acid is a degradation derivative of Nafcillin Sodium, characterized by a beta-lactam-thiazole core fused to a substituted pyrrolidone ring, with a terminal methyl ester group replacing the parent compound's carboxylic acid functionality. Its structure retains the sulfur-containing side chain and amide linkage critical to penicillin's pharmacophore but features esterification at the C-3 position of the uronic acid moiety. This compound arises via hydrolytic cleavage followed by methylation, yielding a stable, non-reactive analog. It serves as an HPLC reference standard for quantifying process-related impurities in Nafcillin Sodium formulations.

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Molecular Formula C22H26N2O6S
Molecular Weight 446.5200
CAS Number N/A
PubChem CID 139025575 ↗
Purity 95%
Product Type API Impurity
Parent Drug Nafcillin Sodium
Lead Time 14 Days
IUPAC Name (2R,4S)-2-((R)-1-(2-ethoxy-1-naphthamido)-2-methoxy-2-oxoethyl)-5,5-dimethylthiazolidine-4-carboxylic acid

📝 Synonyms

Nafcillin Penilloic Acid Methyl Ester (2S,4S)-2-((R)-1-(2-Ethoxy-1-naphthamido)-2-methoxy-2-oxoethyl)-5,5-dimethylthiazolidine-4-carboxylic Acid;

🔬 Chemical Identifiers

C(C)OC1=C(C2=CC=CC=C2C=C1)C(=O)N[C@H](C(=O)OC)[C@H]1SC([C@@H](N1)C(=O)O)(C)C
InChI=1S/C22H26N2O6S/c1-5-30-14-11-10-12-8-6-7-9-13(12)15(14)18(25)23-16(21(28)29-4)19-24-17(20(26)27)22(2,3)31-19/h6-11,16-17,19,24H,5H2,1-4H3,(H,23,25)(H,26,27)/t16-,17-,19+/m0/s1
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