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Substance Name: Epirubicin [INN:BAN]
RN: 56420-45-2
UNII: 3Z8479ZZ5X
InChIKey: AOJJSUZBOXZQNB-VTZDEGQISA-N

Note

  • An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.

Molecular Formula

  • C27-H29-N-O11

Molecular Weight

  • 543.5221
 

Classification Codes

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

Names and Synonyms

Name of Substance

  • Epirubicin
  • Epirubicin [INN:BAN]

MeSH Heading

  • Epirubicin

Synonyms

  • 4'-Epiadriamycin
  • 4'-Epidoxorubicin
  • BRN 1445813
  • CCRIS 2261
  • Ellence
  • Epi-DX
  • Epiadriamycin
  • Epidoxorubicin
  • Epirubicin
  • Epirubicina
  • Epirubicina [INN-Spanish]
  • Epirubicina [Spanish]
  • Epirubicine
  • Epirubicine [French]
  • Epirubicine [INN-French]
  • Epirubicinum
  • Epirubicinum [INN-Latin]
  • Epirubicinum [Latin]
  • HSDB 6962
  • IMI 28
  • NSC 256942
  • Pidorubicina
  • Pidorubicina [INN-Spanish]
  • Pidorubicine
  • Pidorubicine [INN-French]
  • Pidorubicinum
  • Pidorubicinum [INN-Latin]
  • Ridorubicin
  • UNII-3Z8479ZZ5X
  • WP 697

Systematic Names

  • 4-Epidoxorubicin
  • 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-

Registry Numbers

CAS Registry Number

  • 56420-45-2

FDA UNII

  • 3Z8479ZZ5X

Other Registry Number

  • 57918-25-9

Related Registry Number

  • 56390-09-1 (hydrochloride)

System Generated Number

  • 0056420452

Structure Descriptors

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

InChIKey

AOJJSUZBOXZQNB-VTZDEGQISA-N

Smiles

COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[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
dog LD50 intravenous 2mg/kg (2mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Toxicology and Applied Pharmacology. Vol. 79, Pg. 412, 1985.
mouse LD50 intravenous 16070ug/kg (16.07mg/kg)   Toxicology and Applied Pharmacology. Vol. 79, Pg. 412, 1985.
mouse LD50 unreported 29300ug/kg (29.3mg/kg)   Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.
rabbit LDLo intrapleural 400ug/kg (0.4mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"
Pharmacology and Toxicology Vol. 62, Pg. 84, 1988.
rat LD50 intravenous 14270ug/kg (14.27mg/kg)   Toxicology and Applied Pharmacology. Vol. 79, Pg. 412, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 1.850 (none)   EST
Water Solubility 93 mg/L 25 EST
Vapor Pressure 2.50E-23 mm Hg 25 EST
Henry's Law Constant 2.20E-23 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.45E-10 cm3/molecule-sec 25 EST

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