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156263-28-49-Chloroacetamidominocycline

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Catalogue No.:	VE0010327
CAS No.:	156263-28-4
Mol. Formula:	C₂₅H₂₉ClN₄O₈
Mol. Weight:	548.97 g/mol

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Additional information on CAS 156263-28-4

Parent drug

Minocycline

IUPAC Name

(4S,4aS,5aR,12aS)-9-[(2-Chloroacetyl)amino]-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

Synonyms

Minocycline impurity 73;(4S,4aS,5aR,12aS)-9-[(2-Chloroacetyl)amino]-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

Smiles

O=C(C(C1=O)=C(O)[C@@H](N(C)C)[C@]2([H])C[C@]3([H])CC4=C(C(C3=C(O)[C@@]21O)=O)C(O)=C(NC(CCl)=O)C=C4N(C)C)N

InChI

InChI=1S/C25H29ClN4O8/c1-29(2)13-7-12(28-14(31)8-26)19(32)16-10(13)5-9-6-11-18(30(3)4)21(34)17(24(27)37)23(36)25(11,38)22(35)15(9)20(16)33/h7,9,11,18,32,34-35,38H,5-6,8H2,1-4H3,(H2,27,37)(H,28,31)/t9-,11-,18-,25-/m0/s1

Description

9-Chloroacetamidominocycline (CAS 156263-28-4) is a chlorinated acetamido tetracycline-related impurity with molecular formula C25H29ClN4O8 and molecular weight 548.97 g/mol. The presence of the chloroacetamide substituent suggests formation during semisynthetic derivatization or as a process-related side product from acylation chemistry, rather than simple oxidative degradation. Its polarity and ionizable functional groups complicate chromatographic resolution from closely related tetracycline analogues. Quantification typically requires reversed-phase LC-MS/MS with high-resolution MS confirmation, and orthogonal LC-UV or LC-HRMS methods for peak assignment. From a regulatory perspective, this impurity is evaluated as a structurally alerting small molecule under impurity control and genotoxicity assessment frameworks when appropriate.