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Substance Name: Idarubicin [INN:BAN]
RN: 58957-92-9
UNII: ZRP63D75JW
InChIKey: XDXDZDZNSLXDNA-TZNDIEGXSA-N

Note

  • An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.

Molecular Formula

  • C26-H27-N-O9

Molecular Weight

  • 497.4973
 

Classification Codes

  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors

Names and Synonyms

Name of Substance

  • Idarubicin
  • Idarubicin [INN:BAN]

MeSH Heading

  • Idarubicin

Synonyms

  • 4-Demethoxydaunomycin
  • 4-Demethoxydaunorubicin
  • CCRIS 5083
  • Daunomycin, 4-demethoxy-
  • Idarubicin
  • Idarubicina
  • Idarubicina [INN-Spanish]
  • Idarubicine
  • Idarubicine [INN-French]
  • Idarubicinum
  • Idarubicinum [INN-Latin]
  • IMI 30
  • NSC 256439
  • NSC-256439
  • UNII-ZRP63D75JW

Systematic Names

  • 4-Demethoxydaunomycin
  • 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-
  • 5,12-Naphthacenedione, 9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S-cis)-

Registry Numbers

CAS Registry Number

  • 58957-92-9

FDA UNII

  • ZRP63D75JW

Related Registry Number

  • 57852-57-0 (Hydrochloride)

System Generated Number

  • 0058957929

Structure Descriptors

InChI

1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1

InChIKey

XDXDZDZNSLXDNA-TZNDIEGXSA-N

Smiles

C[C@@H]1O[C@H](C[C@H](N)[C@@H]1O)O[C@H]2C[C@@](O)(Cc3c(O)c4C(=O)c5ccccc5C(=O)c4c(O)c23)C(=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3mg/kg (3mg/kg)   Cancer Research. Vol. 48, Pg. 926, 1988.
mouse LD50 intravenous 4mg/kg (4mg/kg) BLOOD: HEMORRHAGE

BLOOD: CHANGES IN SPLEEN
Cancer Treatment Reports. Vol. 61, Pg. 893, 1977.
mouse LD50 oral 16mg/kg (16mg/kg)   Cancer Treatment Reports. Vol. 61, Pg. 893, 1977.
mouse LD50 oral 16mg/kg (16mg/kg) BLOOD: HEMORRHAGE

BLOOD: CHANGES IN SPLEEN
Cancer Treatment Reports. Vol. 61, Pg. 893, 1977.
mouse LD50 unreported 4900ug/kg (4.9mg/kg)   Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 2.100 (none)   EST
Atmospheric OH Rate Constant 1.34E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.