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Daunorubicin information


Daunorubicin
Clinical data
Trade namesCerubidine, others
AHFS/Drugs.comMonograph
MedlinePlusa682289
Pregnancy
category
  • AU: D[1]
Routes of
administration
Intravenous
ATC code
  • L01DB02 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
Pharmacokinetic data
MetabolismLiver
Elimination half-life26.7 hours (metabolite)
ExcretionBile duct and urinary
Identifiers
IUPAC name
  • (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
  • 20830-81-3 checkY
PubChem CID
  • 30323
IUPHAR/BPS
  • 7063
DrugBank
  • DB00694 checkY
ChemSpider
  • 28163 checkY
UNII
  • ZS7284E0ZP
KEGG
  • C01907 checkY
ChEBI
  • CHEBI:41977 checkY
ChEMBL
  • ChEMBL178 checkY
CompTox Dashboard (EPA)
  • DTXSID7022883 Edit this at Wikidata
ECHA InfoCard100.040.048 Edit this at Wikidata
Chemical and physical data
FormulaC27H29NO10
Molar mass527.526 g·mol−1
3D model (JSmol)
  • Interactive image
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)C)O)N)O
InChI
  • 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.

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bladder cancer, and lung cancers. The first anthracycline discovered was daunorubicin (trade name Daunomycin), which is produced naturally by Streptomyces...

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Streptomyces peucetius

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Streptomyces. S. peucetius produces the anthracycline antitumor antibiotics daunorubicin and doxorubicin (also known as adriamycin). Recent work has identified...

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by interfering with the enzyme topoisomerase II. It is an analog of daunorubicin, but the absence of a methoxy group increases its fat solubility and...

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transcription by wedging themselves into the spaces in between DNA's nucleotides Daunorubicin, Doxorubicin, Epirubicin Enzyme inhibitors inhibit enzymes that are crucial...

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Chemotherapy

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mitomycin C and actinomycin. Among the anthracyclines, doxorubicin and daunorubicin were the first, and were obtained from the bacterium Streptomyces peucetius...

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DAT

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dolphins as a therapy DAT (chemotherapy) is a regimen that consists of Daunorubicin, Ara-C (cytarabine) and Thioguanine Divergent Association Test (DAT)...

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DAE

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may refer to: DAE (chemotherapy), a chemotherapy regimen consisting of Daunorubicin, Ara-C (cytarabine) and Etoposide Daporijo Airport, the IATA code for...

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Paclitaxel

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ATC code L01

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L01CX01 Trabectedin L01DA01 Dactinomycin L01DB01 Doxorubicin L01DB02 Daunorubicin L01DB03 Epirubicin L01DB04 Aclarubicin L01DB05 Zorubicin L01DB06 Idarubicin...

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FOLFIRI

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(chemotherapy), a chemotherapy regimen consisting of Ara-C (cytarabine), Daunorubicin and Etoposide Ade (given name) Ade (surname) Adé (singer) Adé, Chad,...

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