ABC01199CT

3-(Isonicotinoylhydrazonomethyl) Rifamycin

3-(Isonicotinoylhydrazonomethyl) Rifamycin is a macrocyclic antibiotic derivative featuring a 16-membered rifamycin scaffold substituted at the C3 position with an isonicotinoylhydrazonomethyl group. The structure incorporates a hydrazine linkage between the isonicotinoyl moiety and the rifamycin core, introducing a hydrazonomethyl bridge. This modification alters the parent drug's pharmacokinetic profile and stability. The compound arises as a synthetic byproduct during rifamycin derivatization processes, specifically during hydrazide coupling reactions. It serves as a critical HPLC reference standard for quantifying process-related impurities in rifamycin-based pharmaceuticals.

On Request
Molecular Formula C44H52N4O13
Molecular Weight 844.9000
CAS Number 13292-53-0
PubChem CID 135459684 ↗
Purity N/A
Product Type API Impurity
Parent Drug Rifamycin
Lead Time On Request
IUPAC Name [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-26-[(E)-(pyridine-4-carbonylhydrazinylidene)methyl]-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

📝 Synonyms

3-Formylrifamycin Isonicotinylhydrazone Isoniazide+Rifapentine Impurity 3-(Isonicotinoylhydrazonomethyl) Rifamycin 13292-53-0 (2S,16S,17S,18R,19R,20R,21S,22R,23S)-5,6,9,17,19-Pentahydroxy-8-[(E)-(isonicotinoylhydrazono)methyl]-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxy[1,11,13]pentadecatrienoimino)naphtho[2,1-b]furan-21-yl acetate [pentahydroxy-methoxy-heptamethyl-dioxo-[(E)-(pyridine-4-carbonylhydrazono)methyl][?]yl] acetate

🔬 Chemical Identifiers

CO[C@H]1/C=C/O[C@]2(OC3=C(C2=O)C4=C(O)C(/C=N/NC(C5=CC=NC=C5)=O)=C(NC(/C(C)=C\C=C\[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(C)=O)C)O)C)O)C)=O)C(O)=C4C(O)=C3C)C
InChI=1S/C44H52N4O13/c1-20-11-10-12-21(2)42(56)47-33-28(19-46-48-43(57)27-13-16-45-17-14-27)37(53)30-31(38(33)54)36(52)25(6)40-32(30)41(55)44(8,61-40)59-18-15-29(58-9)22(3)39(60-26(7)49)24(5)35(51)23(4)34(20)50/h10-20,22-24,29,34-35,39,50-54H,1-9H3,(H,47,56)(H,48,57)/b11-10+,18-15+,21-12-,46-19+/t20-,22+,23+,24+,29-,34-,35+,39+,44-/m0/s1
CKQBSBZAUBPDQB-QPZJDASESA-N

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