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Doxorubicin

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Product Details:

  • Product Name: Doxorubicin
  • CAS #: 23214-92-8
  • Mode of Action:

    Doxorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Doxorubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.

  • Pharmacodynamics:

    Doxorubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Doxorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Doxorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.

  • Toxicity:

    LD50=21800 ug/kg (rat, subcutaneous)

  • IUPAC: (8S, 10S)-10-{[(2R, 4S, 5S, 6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6, 8, 11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5, 7, 8, 9, 10, 12-hexahydrotetracene-5, 12-dione
  • ATC: L01DB01
  • PubChem: 31703
  • DrugBank: DB00997 (APRD00185)
  • Formula: C23H24N2O4S
  • Molecular Mass: 543.5193
  • Synonyms: Doxorubicin HCl Doxorubicin Hydrochloride Doxorubicina [INN-Spanish] Doxorubicine [INN-French] Doxorubicinum [INN-Latin]
  • SMILES: COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O
  • AHFS Code: 10:00.0
  • InChl: AOJJSUZBOXZQNB-TZSSRYMLSA-N
  • General Reference:

    1. Weiss RB: The anthracyclines: will we ever find a better doxorubicin? Semin Oncol. 1992 Dec;19(6):670-86. Pubmed
    2. Tan C, Tasaka H, Yu KP, Murphy ML, Karnofsky DA: Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease. Clinical evaluation with special reference to childhood leukemia. Cancer. 1967 Mar;20(3):333-53. Pubmed
    3. Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C: Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng. 1969 Nov;11(6):1101-10. Pubmed
    4. Di Marco A, Gaetani M, Scarpinato B: Adriamycin (NSC-123, 127): a new antibiotic with antitumor activity. Cancer Chemother Rep. 1969 Feb;53(1):33-7. Pubmed
    5. Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, Inventi-Solari A, Filippini S, Torti F, Colombo AL, Hutchinson CR: Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene. J Bacteriol. 1999 Jan;181(1):305-18. Pubmed

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