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Substance Name: Amrubicin hydrochloride [USAN]
RN: 110311-30-3
UNII: EUL6MP8FZW
InChIKey: BHMLHEQFWVQAJS-IITOGVPQSA-N

Note

  • A 9-amino-anthracycline antibiotic.

Classification Codes

  • Antineoplastic
  • Drug / Therapeutic Agent

Molecular Formula

  • C25-H25-N-O9.Cl-H

Molecular Weight

  • 519.9314
 
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Names and Synonyms

Name of Substance

  • Amrubicin hydrochloride [USAN]
  • SM 5887

Synonyms

  • (+)-(7S,9S)-9-Acetyl-9-amino-7-((2-deoxy-beta-D-erythro-pentopyranosyl)oxy)- 6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride
  • Amrubicin HCl
  • Amrubicin hydrochloride
  • Calsed
  • SM-5887
  • SM5887
  • UNII-EUL6MP8FZW

Systematic Names

  • 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-9-amino-7-((2-deoxy-beta-D-erythro-pentopyranosyl)oxy)-6,11-dihydroxy-, hydrochloride, (7S-cis)-
  • 5,12-Naphthacenedione, 9-acetyl-7-((2-deoxy-beta-D-erythro-pentopyranosyl)oxy)-7,8,9,10-tetrahydro-6,11-dihydroxy-, hydrochloride, (7S,9S)-

Registry Numbers

CAS Registry Number

  • 110311-30-3

FDA UNII

  • EUL6MP8FZW

System Generated Number

  • 0110311303

Molecular Formulas

Molecular Formula

  • C25-H25-N-O9.Cl-H

Molecular Formula Fragments

  • C25-H25-N-O9
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C25H25NO9.ClH/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31;/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3;1H/t14-,15+,16-,17-,25-;/m0./s1

InChIKey

BHMLHEQFWVQAJS-IITOGVPQSA-N

Smiles

Cl.CC(=O)[C@@]1(N)C[C@H](O[C@H]2C[C@H](O)[C@H](O)CO2)c3c(O)c4C(=O)c5ccccc5C(=O)c4c(O)c3C1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 2500ug/kg (2.5mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE Investigational New Drugs. The Journal of New Anticancer Agents. Kluwer Academic Pub., POB 358, Accord Stn., Hingham, MA 02018) V.1- 1983-Vol. 16, Pg. 121, 1998.
mouse LD50 intravenous 32mg/kg (32mg/kg)   Japanese Journal of Cancer Research. Vol. 80, Pg. 77, 1989.
mouse LD50 intravenous 32mg/kg (32mg/kg) BEHAVIORAL: ATAXIA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Japanese Journal of Cancer Research. Vol. 80, Pg. 77, 1989.