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CAS 23541-50-6

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Daunorubicin hydrochloride

Description:
Daunorubicin hydrochloride is an anthracycline antibiotic derived from the bacterium Streptomyces peucetius, primarily used in cancer therapy, particularly for treating acute myeloid leukemia and acute lymphoblastic leukemia. It exhibits a red-orange color and is known for its potent cytotoxic properties, which interfere with DNA replication and transcription by intercalating into DNA strands and inhibiting topoisomerase II. This mechanism leads to apoptosis in rapidly dividing cancer cells. Daunorubicin hydrochloride is typically administered intravenously and has a well-documented side effect profile, including cardiotoxicity, myelosuppression, and potential for secondary malignancies. Its solubility in water is enhanced by the hydrochloride salt form, making it suitable for clinical use. The compound's pharmacokinetics involve hepatic metabolism and renal excretion, and it is often used in combination with other chemotherapeutic agents to enhance therapeutic efficacy. Due to its significant therapeutic benefits and associated risks, careful monitoring during treatment is essential.
Formula:C27H29NO10·ClH
InChI:InChI=1S/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22+,27-;/m0./s1
InChI key:InChIKey=GUGHGUXZJWAIAS-QQYBVWGSSA-N
SMILES:OC=1C2=C([C@@H](O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C[C@@](C(C)=O)(O)C2)C(O)=C4C1C(=O)C=5C(C4=O)=C(OC)C=CC5.Cl
Synonyms:
  • (1R,3R)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-D-lyxo-hexopyranoside hydrochloride
  • (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxyhexopyranoside hydrochloride
  • 5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, hydrochloride (1:1), (8S,10S)-
  • 5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, hydrochloride, (8S,10S)-
  • 5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-<span class="text-smallcaps">L</span>-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, hydrochloride, (8S-cis)-
  • Cerubidine
  • Daunoblastin
  • Daunomycin chlorohydrate
  • Daunorubicin hydrochloride
  • Daunorubicin, HCl
  • See more synonyms
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