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CAS 92689-49-1

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Annamycin

Description:
Annamycin is a synthetic anthracycline antibiotic that is primarily investigated for its potential use in cancer treatment, particularly for its efficacy against certain types of leukemia and solid tumors. It is structurally related to doxorubicin but is designed to have a reduced cardiotoxicity profile, which is a significant side effect associated with many anthracyclines. Annamycin functions by intercalating into DNA, thereby inhibiting topoisomerase II and disrupting the replication and transcription processes of cancer cells. This mechanism leads to apoptosis, or programmed cell death, in malignant cells. In addition to its antitumor activity, Annamycin has been studied for its ability to overcome multidrug resistance, a common challenge in cancer therapy. Its pharmacokinetics, including absorption, distribution, metabolism, and excretion, are critical for determining its therapeutic efficacy and safety profile. Ongoing research aims to further elucidate its potential benefits and optimize its use in clinical settings.
Formula:C26H25IO11
InChI:InChI=1S/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3/t9-,13-,18+,19-,24-,25-,26-/m0/s1
InChI key:InChIKey=CIDNKDMVSINJCG-GKXONYSUSA-N
SMILES:OC=1C2=C([C@@H](O[C@H]3[C@H](I)[C@H](O)[C@@H](O)[C@H](C)O3)C[C@@](C(CO)=O)(O)C2)C(O)=C4C1C(=O)C=5C(C4=O)=CC=CC5
Synonyms:
  • (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,6-dideoxy-2-iodo-alpha-L-mannopyranoside
  • (7S,9S)-7-[(2,6-Dideoxy-2-iodo-α-<span class="text-smallcaps">L</span>-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-5,12-naphthacenedione
  • (7S,9S)-7-[(2R,3R,4R,5R,6S)-4,5-Dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione
  • 5,12-Naphthacenedione, 7-[(2,6-dideoxy-2-iodo-α-<span class="text-smallcaps">L</span>-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-, (7S,9S)-
  • 5,12-Naphthacenedione, 7-[(2,6-dideoxy-2-iodo-α-<span class="text-smallcaps">L</span>-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-, (7S,9S)-
  • Annamycin
  • 5,12-Naphthacenedione, 7-[(2,6-dideoxy-2-iodo-α-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(hydroxyacetyl)-, (7S,9S)-
  • Naxtarubicin
  • (7S,9S)-7-[(2,6-Dideoxy-2-iodo-α-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-5,12-naphthacenedione
  • 5,12-Naphthacenedione, 7-[(2,6-dideoxy-2-iodo-α-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-, (7S,9S)-
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