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Substance Name: Epirubicin hydrochloride [USAN:USP:JAN]
RN: 56390-09-1
UNII: 22966TX7J5
InChIKey: MWWSFMDVAYGXBV-FGBSZODSSA-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.Cl-H

Molecular Weight

  • 579.983
 

Classification Codes

  • Antineoplastic
  • Drug / Therapeutic Agent
  • Human Data

Names and Synonyms

Name of Substance

  • Epirubicin hydrochloride [USAN:USP:JAN]

Synonyms

  • (1S,3S)-3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside hydrochloride
  • 4'-epi-Adriamycin hydrochloride
  • 4'-Epidoxorubicin hydrochloride
  • CCRIS 4477
  • EINECS 260-145-2
  • Ellence
  • Epidoxorubicin hydrochloride
  • Epirubicin HCl
  • Epirubicin hydrochloride
  • Epirubitec
  • Farmorubicin
  • IMI-28
  • NSC 256942
  • Pharmorubicin
  • UNII-22966TX7J5

Systematic Names

  • (8S-cis)-10-((3-Amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacene-5,12-dione hydrochloride
  • 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S-cis)-
  • 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-arabinohexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S,10S)-
  • Farmorubicin

Registry Numbers

CAS Registry Number

  • 56390-09-1

FDA UNII

  • 22966TX7J5

Related Registry Number

  • 56420-45-2 (Parent)

System Generated Number

  • 0056390091

Molecular Formulas

Molecular Formula

  • C27-H29-N-O11.Cl-H

Molecular Formula Fragments

  • C27-H29-N-O11
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C27H29NO11.ClH/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;1H/t10-,13-,15-,17-,22-,27-;/m0./s1

InChIKey

MWWSFMDVAYGXBV-FGBSZODSSA-N

Smiles

O1[C@@H](C)[C@@H]([C@H](C[C@@H]1O[C@@H]1c2c(c(c3C(c4cccc(c4C(c3c2O)=O)OC)=O)O)C[C@](C(CO)=O)(O)C1)N)O.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 2250ug/kg (2.25mg/kg)   Drugs in Japan Vol. -, Pg. 200, 1990.
mouse LD50 intravenous 31500ug/kg (31.5mg/kg)   Drugs in Japan Vol. -, Pg. 200, 1990.
mouse LD50 oral > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. -, Pg. 200, 1990.
mouse LD50 subcutaneous 37500ug/kg (37.5mg/kg)   Drugs in Japan Vol. -, Pg. 200, 1990.
rat LD50 intraperitoneal 10800ug/kg (10.8mg/kg)   Drugs in Japan Vol. -, Pg. 200, 1990.
rat LD50 intravenous 17mg/kg (17mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 740, 1995.
rat LD50 oral 1350mg/kg (1350mg/kg)   Drugs in Japan Vol. -, Pg. 200, 1990.
rat LD50 subcutaneous 17600ug/kg (17.6mg/kg)   Drugs in Japan Vol. -, Pg. 200, 1990.
women TDLo intravenous 1622mg/kg (1622mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Lancet. Vol. 2, Pg. 629, 1986.