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CAS 110311-30-3

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Amrubicin hydrochloride

Description:
Amrubicin hydrochloride is an anthracycline derivative primarily used as an antineoplastic agent in cancer therapy. It exhibits a mechanism of action that involves intercalation into DNA, leading to the inhibition of topoisomerase II, which disrupts DNA replication and transcription, ultimately inducing apoptosis in cancer cells. This compound is particularly noted for its efficacy against various types of solid tumors and hematological malignancies. Amrubicin hydrochloride is characterized by its relatively high lipophilicity, which enhances its cellular uptake. The hydrochloride salt form improves its solubility in aqueous solutions, facilitating its administration via intravenous routes. Common side effects associated with amrubicin hydrochloride include myelosuppression, cardiotoxicity, and gastrointestinal disturbances, necessitating careful monitoring during treatment. Its pharmacokinetics involve metabolism primarily in the liver, with excretion occurring through urine. Overall, amrubicin hydrochloride represents a significant therapeutic option in oncology, particularly for patients with resistant or relapsed cancers.
Formula:C25H25NO9·ClH
InChI:InChI=1S/C25H25NO9.ClH/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31;/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3;1H/t14-,15+,16-,17-,25-;/m0./s1
InChI key:InChIKey=BHMLHEQFWVQAJS-IITOGVPQSA-N
SMILES:O([C@@H]1C2=C(C(O)=C3C(=C2O)C(=O)C=4C(C3=O)=CC=CC4)C[C@](C(C)=O)(N)C1)[C@H]5C[C@H](O)[C@H](O)CO5.Cl
Synonyms:
  • SM 5887
  • 5,12-Naphthacenedione, 9-acetyl-9-amino-7-[(2-deoxy-β-D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-, hydrochloride, (7S-cis)-
  • Amrubicin hydrochloride
  • 5,12-Naphthacenedione, 9-acetyl-9-amino-7-[(2-deoxy-β-D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-, hydrochloride, (7S,9S)-
  • 5,12-Naphthacenedione, 9-acetyl-9-amino-7-[(2-deoxy-β-D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-, hydrochloride (1:1), (7S,9S)-
Found 3 products.