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Substance Name: 3'-Deamino-3'-hydroxydoxorubicin
RN: 73113-90-3
UNII: M61CNW3494
InChIKey: HEQRYQONNHFDHG-TZSSRYMLSA-N

Note

  • Substitution of the basic amino group at the C-3' of doxorubicin by a hydroxyl group overcomes recognition of the multidrug resistant P-glycoprotein and limits cardiotoxicity.

Molecular Formula

  • C27-H28-O12

Molecular Weight

  • 544.5062
 

Classification Codes

  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors
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Names and Synonyms

Name of Substance

  • 3'-Deamino-3'-hydroxydoxorubicin

Synonyms

  • BRN 5205491
  • Hydroxydoxorubicin
  • Hydroxyrubicin
  • UNII-M61CNW3494

Systematic Names

  • 5,12-Naphthacenedione, 10-((2,6-dideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-
  • 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-10-((2,6-dideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-8-(hydroxyacetyl)-1-methoxy-6,8,11-trihydroxy-, (8S-cis)-

Registry Numbers

CAS Registry Number

  • 73113-90-3

FDA UNII

  • M61CNW3494

System Generated Number

  • 0073113903

Structure Descriptors

InChI

1S/C27H28O12/c1-10-22(31)13(29)6-17(38-10)39-15-8-27(36,16(30)9-28)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/h3-5,10,13,15,17,22,28-29,31,33,35-36H,6-9H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1

InChIKey

HEQRYQONNHFDHG-TZSSRYMLSA-N

Smiles

COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](O)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 79mg/kg (79mg/kg)   Anti-Cancer Drugs. Vol. 4, Pg. 37, 1993.