Structure via PubChem · Public domain (PubChem)
daunorubicin
Sign in to saveAlso known as Cerubidine®, daunomycin, FI-6339, NDC-0082-4155, RP-13057, Daunorubicinum, Daunomycin, (8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione
Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically it is used for acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. It is administered by injection into a vein. A liposomal formulation known as liposomal daunorubicin also exists.
Chemical data
- Formula
- C27H29NO10
- Molecular weight
- 527.5 g/mol
- IUPAC name
- (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
- SMILES
- C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O
- InChIKey
- STQGQHZAVUOBTE-VGBVRHCVSA-N
- XLogP
- 1.8
- Polar surface area
- 186 Ų
- H-bond donors
- 5
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1979
- Admin. routes
- parenteral
- Indications
- neoplasm, acute myeloid leukemia, leukemia, acute lymphoblastic leukemia
via ChEMBL · EBI
Research
81,004 papers- Daunorubicin/Cytarabine Liposome: A Review in Acute Myeloid Leukaemia.Drugs · 2018
- Daunorubicin and Cytarabine Liposome in Newly Diagnosed Therapy-Related Acute Myeloid Leukemia (AML) or AML With Myelodysplasia-Related Changes.The Annals of pharmacotherapy · 2018
- Production of daunorubicin.Advances in biotechnological processes · 1984
- Daunorubicin and doxorubicin, anthracycline antibiotics, a physicochemical and biological review.Biochimie · 1984
- Daunorubicin and its hydroxy metabolite in cardiomyocytes: insights into cellular kinetics, toxicity, DNA damage, and dexrazoxane-induced cardioprotection.Archives of toxicology · 2025
via PubMed
Wikidata facts
- Subclass of
- anthracycline antibiotic
- Mass
- 527.179
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₇H₂₉NO₁₀
- subject has role
- topoisomerase inhibitor
- canonical SMILES
- CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)C)O)N)O
- isomeric SMILES
- C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)C)O)N)O
- MCN code
- 3004.20.62
- World Health Organisation international non-proprietary name
- daunorubicin
- Commons category
- Daunorubicin
- stylized name
- DAUNOrubicin
via Wikidata · CC0
~5 min read
Encyclopedic overview
5 sectionsContents
- Medical uses
- Mechanism of action
- History
- Route of administration
- References
Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically it is used for acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. It is administered by injection into a vein. A liposomal formulation known as liposomal daunorubicin also exists.
Common side effects include hair loss, vomiting, bone marrow suppression, and inflammation of the inside of the mouth. Other severe side effects include heart disease and tissue death at the site of injection. Use in pregnancy may harm the fetus. Daunorubicin is in the anthracycline family of medication. It works in part by blocking the function of topoisomerase II.
Excerpted from Wikipedia’s “daunorubicin” article, available under the CC BY-SA 4.0 licence.