94703-34-1Amoxicillin Trimer Impurity

● Under Development

Catalogue No.:	VL1970019
CAS No.:	94703-34-1
Mol. Formula:	C48H54N9Na3O15S3 .
Mol. Weight:	1162.16

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Additional information on CAS 94703-34-1

Parent drug

Amoxicillin

IUPAC Name

(2R,2’R,4S,4’S)-2,2′-((1R,4S,7R,10R)-1-amino-14-(((2S,5R,6R)-2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl)amino)-1,7,13-tris(4-hydroxyphenyl)-2,5,8,11,14-pentaoxo-3,6,9,12-tetraazatetradecane-4,10-diyl)bis(5,5-dimethylthiazolidine-4-carboxylic acid) Trisodium Salt

Pharmacopeial Synonyms

N/A

Synonyms

N/A

Smiles

O=C(N[C@H]1[C@@]2([H])SC(C)(C)[C@H](C([O-])=O)N2C1=O)C(C3=CC=C(O)C=C3)NC([C@H]([C@H]4SC(C)(C)[C@H](C([O-])=O)N4)NC([C@@H](C5=CC=C(O)C=C5)NC([C@@H]([C@H]6SC(C)(C)[C@H](C([O-])=O)N6)NC([C@H](N)C7=CC=C(O)C=C7)=O)=O)=O)=O.[Na+].[Na+].[Na+]

InChI

InChI=1S/C48H57N9O15S3.3Na/c1-46(2)31(43(67)68)55-39(73-46)28(52-34(61)25(49)19-7-13-22(58)14-8-19)37(64)50-26(20-9-15-23(59)16-10-20)35(62)53-29(40-56-32(44(69)70)47(3,4)74-40)38(65)51-27(21-11-17-24(60)18-12-21)36(63)54-30-41(66)57-33(45(71)72)48(5,6)75-42(30)57;;;/h7-18,25-33,39-40,42,55-56,58-60H,49H2,1-6H3,(H,50,64)(H,51,65)(H,52,61)(H,53,62)(H,54,63)(H,67,68)(H,69,70)(H,71,72);;;/q;3*+1/p-3/t25-,26-,27?,28+,29-,30-,31+,32+,33+,39-,40-,42-;;;/m1…/s1

Description

Amoxicillin Trimer Impurity (CAS 94703-34-1) is a multimeric degradation product formed by condensation and trimerization of amoxicillin under thermal, acidic or aqueous stress conditions, posing risks to potency and stability. Analytical characterization requires sensitive LC-MS and HPLC methods with validated limits of detection and quantification, supported by NMR and HRMS for structural confirmation. Control strategies include optimized synthesis and purification, stringent solvent selection, and in-process monitoring to limit formation. Accurate impurity profiling and specification setting in line with ICH guidelines enable risk assessment, batch release decisions and regulatory compliance for amoxicillin drug substance manufacture.

References

Huttner, A., et al. Oral Amoxicillin and Amoxicillinâ€“Clavulanic Acid: Properties, Indications and Usage.â€ Clinical Microbiology and Infection, vol. 26, no. 7, July 2020, pp. 871â€“879, 10.1016/j.cmi.2019.11.028.