Desmethyl Rifampicin
Desmethyl Rifampicin is a rifamycin-derived impurity arising from demethylation of the methyl group at the C-17 position of Rifampicin. It retains the naphthoquinone core, enediyne chromophore, and cyclohexadecyl side chain but lacks the terminal methyl substitution critical for macrocyclic lactam formation. This structural modification reduces its antibiotic activity while preserving chromatographic similarity to the parent compound. It functions as an HPLC reference standard for quantifying process-related impurities in Rifampicin formulations.
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Molecular Formula
C42H56N4O12
Molecular Weight
808.9000
CAS Number
13292-45-0
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PubChem CID
135554537 ↗
IUPAC Name
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21E)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-26-[(E)-piperazin-1-yliminomethyl]-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate
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📝 Synonyms
N-Demethyl Rifampin
Demethylrifampicin
13292-45-0
Rifampicin AF/AP
4-N-Demethylrifampicin
N-Demethyl Rifampicin
Rifampicin, D-methyl
N-Demethylrifampin
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21E)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-26-[(E)-piperazin-1-yliminomethyl]-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate
AF/AP
🔬 Chemical Identifiers
C[C@H]1/C=C/C=C(/C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C=N/N5CCNCC5)\C
InChI=1S/C42H56N4O12/c1-20-11-10-12-21(2)41(54)45-32-27(19-44-46-16-14-43-15-17-46)36(51)29-30(37(32)52)35(50)25(6)39-31(29)40(53)42(8,58-39)56-18-13-28(55-9)22(3)38(57-26(7)47)24(5)34(49)23(4)33(20)48/h10-13,18-20,22-24,28,33-34,38,43,48-52H,14-17H2,1-9H3,(H,45,54)/b11-10+,18-13+,21-12+,44-19+/t20-,22+,23+,24+,28-,33-,34+,38+,42-/m0/s1
FKKVFHDDYXJFFL-MOSFFKILSA-N
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