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CAS 23214-92-8

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Doxorubicin

Description:
Doxorubicin, also known by its brand name Adriamycin, is an anthracycline antibiotic used primarily in cancer chemotherapy. It is derived from the bacterium Streptomyces peucetius and is characterized by its red color, which is indicative of its anthracycline structure. The chemical formula of doxorubicin is C27H29NO11, and it has a molecular weight of approximately 579.65 g/mol. Doxorubicin functions by intercalating into DNA, disrupting the replication process, and inhibiting topoisomerase II, which ultimately leads to apoptosis in rapidly dividing cancer cells. Its therapeutic applications include the treatment of various cancers, such as breast cancer, leukemia, and lymphoma. However, doxorubicin is associated with significant side effects, including cardiotoxicity, which limits its cumulative dose. It is typically administered intravenously and is often used in combination with other chemotherapeutic agents to enhance efficacy. Due to its potent effects and potential toxicity, careful monitoring during treatment is essential.
Formula:C27H29NO11
InChI:InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
InChI key:InChIKey=AOJJSUZBOXZQNB-TZSSRYMLSA-N
SMILES:OC=1C2=C([C@@H](O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C[C@@](C(CO)=O)(O)C2)C(O)=C4C1C(=O)C=5C(C4=O)=C(OC)C=CC5
Synonyms:
  • (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
  • (7S,9S)-7-[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,1 1-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
  • (8S,10S)-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-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
  • (8S-cis)-10-(3-Amino-2,3,6-Trideoxy-alpha-L-Lyxo-Hexopyranosyl)Oxy-7,8,9,10-Tetrahydro-6,8,11-Trihydroxy-8-(Hydroxyacetyl)-1-Methoxy-5,12-Naphthacenedione
  • 10-((3-Amino-2,3,6-trideoxy-alpha-L-lyso-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
  • 14-Hydroxydaunomycin
  • 5,12-Naphthacenedione, 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-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-
  • 5,12-Naphthacenedione, 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-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-
  • 5,12-Naphthacenedione, 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-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
  • 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-
  • See more synonyms
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