125833-03-6Rifampicin EP Impurity B

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Catalogue No.:	VL2760001
CAS No.:	125833-03-6
Mol. Formula:	C43H58N4O13
Mol. Weight:	838.94 g/mol

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Additional information on CAS 125833-03-6

Parent drug

Rifampicin

IUPAC Name

(4-({[(2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-21-Acetoxy-5,6,9,17,19-pentahydroxy-23-methoxy2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2,6,9-tetrahydro-2,7- (epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-8-yl]methylene}amino)-1-methylpiperazine 1-oxide)

Synonyms

N/A

Smiles

O=C1NC2=C(/C=N/N3CCN(C)CC3)C(O)=C4C(C(O)=C(C)C(O[C@]5(C)O/C=C/[C@]([H])(OC)[C@](C)([H])[C@](OC(C)=O)([H])[C@@](C)([H])[C@]([H])(O)[C@]([H])(C)[C@@]([H])(O)[C@](C)([H])/C=C/C=C1/C)=C4C5=O)=C2O>>[O]

InChI

InChI=1S/C43H58N4O12.O/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49;/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55);/b12-11+,19-14+,22-13-,44-20+;/t21-,23+,24+,25+,29?,34-,35+,39+,43-;/m0./s1

Description

Rifampicin EP Impurity B, CAS 125833-03-6, is rifampicin N-oxide, a tertiary amine oxidation product of the ansamycin macrocycle rather than a structural rearrangement impurity. Its molecular formula, C43H58N4O13, and molecular weight, 838.94 g/mol, reflect insertion of a single oxygen atom relative to rifampicin. Formation is typically associated with oxidative degradation during manufacture, storage, or sample handling under light or peroxide exposure. Because the parent scaffold is highly conjugated and prone to epimerization and redox interconversion, characterization commonly requires LC-MS/MS, high-resolution LC-HRMS, and diode array detection, with chromatographic resolution from rifampicin and related oxidative species.