297175-66-7Amoxicilloic Acid Dimer (Mixture of Diastereomers)

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Catalogue No.:	VE0011134
CAS No.:	297175-66-7
Mol. Formula:	C31H40N6O9S2
Mol. Weight:	704.81 g/mol

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Additional information on CAS 297175-66-7

Parent drug

Amoxicillin

IUPAC Name

(2S,4S)-2-((R)-1-((R)-2-Amino-2-(4-hydroxyphenyl)acetamido)-2-(((R)-2-((((2S,4S)-4-carboxy-5,5-dimethylthiazolidin-2-yl)methyl)amino)-1-(4-hydroxyphenyl)-2-oxoethyl)amino)-2-oxoethyl)-5,5-dimethylthiazolidine-4-carboxylic Acid

Pharmacopoeial Synonyms

N/A

Other Synonyms

N/A

InChI

InChI=1S/C31H40N6O9S2/c1-30(2)22(28(43)44)34-18(47-30)13-33-25(41)20(15-7-11-17(39)12-8-15)35-26(42)21(27-37-23(29(45)46)31(3,4)48-27)36-24(40)19(32)14-5-9-16(38)10-6-14/h5-12,18-23,27,34,37-39H,13,32H2,1-4H3,(H,33,41)(H,35,42)(H,36,40)(H,43,44)(H,45,46)/t18-,19+,20+,21+,22-,23-,27-/m0/s1

Smiles

O=C([C@@H]1N[C@H]([C@H](NC([C@H](N)C2=CC=C(O)C=C2)=O)C(N[C@H]C3=CC=C(O)C=C3)C(NC[C@@H]4SC(C)(C)[C@H](C(O)=O)N4)=O)=O)SC1(C)C)O

Description

Amoxicilloic Acid Dimer (Mixture of Diastereomers), also described as Amoxicilloic Amoxilloic Acid Dimers 1, 2, 3, and 4, CAS 297175-66-7, is a penicillanic acid dimer related to amoxicillin hydrolytic degradation. The molecular formula C31H40N6O9S2 and molecular weight 704.81 g/mol indicate a sulfur containing, β-lactam derived impurity with multiple stereogenic centers, hence diastereomeric complexity. Formation is consistent with acyl side chain coupling after β-lactam ring opening during storage or processing under aqueous stress. Characterization typically requires LC-MS/MS with high resolution MS and orthogonal reversed phase or chiral LC to resolve isomers; NMR may support structural assignment. The impurity is of regulatory interest because degradants from penicillins may affect product stability profiles.