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Substance Name: Pirarubicin [INN:JAN]
RN: 72496-41-4
UNII: D58G680W0G
InChIKey: KMSKQZKKOZQFFG-YXRRJAAWSA-N

Classification Codes

  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Mutation Data

Molecular Formula

  • C32-H37-N-O12

Molecular Weight

  • 627.6393
 
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Names and Synonyms

Name of Substance

  • Pirarubicin
  • Pirarubicin [INN:JAN]

Synonyms

  • (2''R)-4'-O-Tetrahydropyranyladriamycin
  • (8S,10S)-10-((3-Amino-2,3,6-trideoxy-4-O-(2R-tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
  • 1609RB
  • 4'-O-Tetrahydropyranyladriamycin
  • 4'-O-Tetrahydropyranyldoxorubicin
  • Pirarubicin
  • Pirarubicina
  • Pirarubicina [Spanish]
  • Pirarubicine
  • Pirarubicine [French]
  • Pirarubicinum
  • Pirarubicinum [Latin]
  • THP-adriamycin
  • UNII-D58G680W0G

Systematic Names

  • (8S,10S)-10-((3-Amino-2,3,6-trideoxy-4-O-(2R-tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione
  • 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-4-O-(tetrahydro-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-

Registry Numbers

CAS Registry Number

  • 72496-41-4

FDA UNII

  • D58G680W0G

Other Registry Number

  • 70259-49-3

System Generated Number

  • 0072496414

Structure Descriptors

InChI

1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1

InChIKey

KMSKQZKKOZQFFG-YXRRJAAWSA-N

Smiles

C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)CO)O)N)O[C@@H]6CCCCO6

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 27800ug/kg (27.8mg/kg)   Journal of Antibiotics. Vol. 32, Pg. 1082, 1979.
mouse LD50 unreported 14mg/kg (14mg/kg)   Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.