Pirarubicin

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Pirarubicin
Pirarubicin.png
Clinical data
Other names(9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2R)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-4-O-[(2R)-tetrahydro-2H-pyran-2-yl]-α-L-lyxo-hexopyranoside
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC32H37NO12
Molar mass627.643 g·mol−1
3D model (JSmol)
Melting point188 to 192 °C (370 to 378 °F) (decomposes)
  • C[C@H]1[C@H]([C@H](C[C@@H](O1)OC2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O[C@@H]6CCCCO6
  • 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 ☒N
  • Key:KMSKQZKKOZQFFG-YHKVCKOMSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Pirarubicin (INN) is an anthracycline drug. An analogue of the anthracycline antineoplastic antibiotic doxorubicin. Pirarubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. This agent is less cardiotoxic than doxorubicin and exhibits activity against some doxorubicin-resistant cell lines.[1]

References

  1. ^ Miller AA, Salewski E (1994). "Prospects for pirarubicin". Medical and Pediatric Oncology. 22 (4): 261–8. doi:10.1002/mpo.2950220410. PMID 8107658.