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CHEBI:231680 - aldoxorubicin

Default Structure
ChEBI IDCHEBI:231680
ChEBI Namealdoxorubicin
Stars
DefinitionAldoxorubicin is a 6-maleimidocaproyl hydrazone derivative prodrug of the anthracycline antibiotic doxorubicin (DOXO-EMCH) with antineoplastic activity. Following intravenous administration, aldoxorubicin binds selectively to the cysteine-34 position of albumin via its maleimide moiety. Doxorubicin is released from the albumin carrier after cleavage of the acid-sensitive hydrazone linker within the acidic environment of tumors and, once located intracellularly, intercalates DNA, inhibits DNA synthesis, and induces apoptosis. Albumin tends to accumulate in solid tumors as a result of high metabolic turnover, rapid angiogenesis, hypervasculature, and impaired lymphatic drainage. Because of passive accumulation within tumors, this agent may improve the therapeutic effects of doxorubicin while minimizing systemic toxicity. (NCIt)
Submitteramillett1
DownloadsMolfile
FormulaC37H42N4O13
Net Charge0
Average Mass750.758
Monoisotopic Mass750.27484
SMILESCOc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)CC(O)(/C(CO)=N/NC(=O)CCCCCN1C(=O)C=CC1=O)CC3OC1CC(N)C(O)C(C)O1
InChIInChI=1S/C37H42N4O13/c1-17-32(46)20(38)13-27(53-17)54-22-15-37(51,23(16-42)39-40-24(43)9-4-3-5-12-41-25(44)10-11-26(41)45)14-19-29(22)36(50)31-30(34(19)48)33(47)18-7-6-8-21(52-2)28(18)35(31)49/h6-8,10-11,17,20,22,27,32,42,46,48,50-51H,3-5,9,12-16,38H2,1-2H3,(H,40,43)/b39-23+
InChIKeyOBMJQRLIQQTJLR-JRZNSJKLSA-N
ChEBI Ontology
Outgoing Relation(s)
aldoxorubicin (CHEBI:231680) is a organic molecular entity (CHEBI:50860)