Daunorubicin

Daunorubicin
Clinical data
Trade namesCerubidine, others
AHFS/Drugs.comMonograph
MedlinePlusa682289
Pregnancy
category
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
Elimination half-life26.7 hours (metabolite)
ExcretionBile duct and urinary
Identifiers
  • (8S,10S)-8-Acetyl-10-[(2S,4S,5S,6S)-
    4-amino-5-hydroxy-6-methyl-oxan-
    2-yl]oxy-6,8,11-trihydroxy-1-methoxy-
    9,10-dihydro-7H-tetracene-5,12-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.040.048 Edit this at Wikidata
Chemical and physical data
FormulaC27H29NO10
Molar mass527.526 g·mol−1
3D model (JSmol)
  • 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)C)O)N)O
  • InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1 checkY
  • Key:STQGQHZAVUOBTE-VGBVRHCVSA-N checkY
  (verify)

Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer.[2] Specifically it is used for acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma.[2] It is administered by injection into a vein.[2] A liposomal formulation known as liposomal daunorubicin also exists.[2]

Common side effects include hair loss, vomiting, bone marrow suppression, and inflammation of the inside of the mouth.[2] Other severe side effects include heart disease and tissue death at the site of injection.[2] Use in pregnancy may harm the fetus.[2] Daunorubicin is in the anthracycline family of medication.[3] It works in part by blocking the function of topoisomerase II.[2]

Daunorubicin was approved for medical use in the United States in 1979.[2] It is on the World Health Organization's List of Essential Medicines.[4] It was originally isolated from bacteria of the Streptomyces type.[5]

  1. ^ "Daunorubicin (Cerubidine) Use During Pregnancy". Drugs.com. 19 September 2019. Retrieved 15 August 2020.
  2. ^ a b c d e f g h i "Daunorubicin hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 8 January 2017. Retrieved 8 December 2016.
  3. ^ British National Formulary: BNF 69 (69th ed.). British Medical Association. 2015. pp. 581–583. ISBN 9780857111562.
  4. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  5. ^ Lin GQ, You QD, Cheng JF (2011). Chiral Drugs: Chemistry and Biological Action. John Wiley & Sons. p. 120. ISBN 9781118075630. Archived from the original on 21 December 2016.