43168-51-0Minocycline EP Impurity A

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Catalogue No.:	VE0017078
CAS No.:	43168-51-0
Mol. Formula:	C23H27N3O7
Mol. Weight:	457.48 g/mol

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Additional information on CAS 43168-51-0

Parent drug

Minocycline

IUPAC Name

(4R,4aS,5aR,12aS)-4,7-bis(dimethylamino)-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

Pharmacopoeial Synonyms

4-Epi Minocycline

Other Synonyms

2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4R,4aS,5aR,12aS)-

Smiles

CN(C)[C@@H]1[C@@H]2C[C@@H]3CC4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)N(C)C

InChI

InChI=1S/C23H27N3O7/c1-25(2)12-5-6-13(27)15-10(12)7-9-8-11-17(26(3)4)19(29)16(22(24)32)21(31)23(11,33)20(30)14(9)18(15)28/h5-6,9,11,17,27-28,31,33H,7-8H2,1-4H3,(H2,24,32)/t9-,11-,17+,23-/m0/s1

Description

Minocycline EP Impurity A, identified as 4-Epi Minocycline (CAS 43168-51-0), is a stereochemical epimer of the tetracycline-class antibiotic minocycline rather than a new covalent degradant. The impurity arises through epimerization at the C-4 dimethylamino-bearing center under acidic, thermal, or aqueous stress, yielding a closely related diastereomer with altered chromatographic and pharmacological behavior. Its molecular formula is C23H27N3O7 and molecular weight is 457.48 g/mol. Because of its structural similarity to the active drug, separation and quantification commonly require high-resolution RP-HPLC with UV or MS detection, and confirmation by LC-MS/MS or NMR. Regulatory assessment focuses on process- and stability-related impurity control.