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CAS 58957-92-9

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Idarubicin

Description:
Idarubicin is an anthracycline antibiotic and an antineoplastic agent primarily used in cancer chemotherapy. It is derived from daunorubicin and is known for its potent cytotoxic effects against various types of cancer, particularly acute myeloid leukemia and certain lymphomas. The chemical formula of idarubicin is C26H27N3O9, and it features a complex polycyclic structure that includes an anthraquinone moiety, which is crucial for its mechanism of action. Idarubicin works by intercalating into DNA, disrupting the replication process, and generating free radicals that contribute to cellular damage. Its pharmacokinetics involve rapid distribution in tissues, with metabolism primarily occurring in the liver. The drug is administered intravenously and has a notable side effect profile, including myelosuppression, cardiotoxicity, and gastrointestinal disturbances. Due to its efficacy and toxicity, idarubicin is typically used in combination with other chemotherapeutic agents to enhance treatment outcomes while managing adverse effects.
Formula:C26H27NO9
InChI:InChI=1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1
InChI key:InChIKey=XDXDZDZNSLXDNA-TZNDIEGXSA-N
SMILES:O([C@@H]1C2=C(C(O)=C3C(=C2O)C(=O)C=4C(C3=O)=CC=CC4)C[C@](C(C)=O)(O)C1)[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5
Synonyms:
  • 4-Demethoxydaunorubicin
  • (7S,9S)-9-Acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione
  • 5,12-Naphthacenedione, 9-acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S,9S)-
  • 4-Demethoxydaunomycin
  • 5,12-Naphthacenedione, 9-acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S-cis)-
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