daunorubicin   Click here for help

GtoPdb Ligand ID: 7063

Synonyms: Cerubidine® | daunomycin | FI-6339 | NDC-0082-4155 | RP-13057
Approved drug PDB Ligand
daunorubicin is an approved drug (FDA (1979), EMA (2018))
Comment: Daunorubicin is an anthracycline class chemotherapeutic for cancer treatment.
Daunorubicin is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 4
Topological polar surface area 185.84
Molecular weight 527.18
XLogP 0.56
No. Lipinski's rules broken 0
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Canonical SMILES COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)C(OC1CC(N)C(C(O1)C)O)CC(C2)(O)C(=O)C
Isomeric SMILES COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)C(=O)C
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
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Summary of Clinical Use Click here for help
Daunorubicin is indicated for treatment of remissions of acute myelogenous and lymphocytic leukemias and may also be used to treat HIV-associated Kaposi's sarcoma. In the EU, daunorubicin monotherapy is indicated for use only in orphan disease, namely acute myeloid leukemia. In August 2017 the US FDA approved a fixed-dose combination of daunorubicin and cytarabine (Vyxeos®) for the treatment of adults with two types of acute myeloid leukemia (AML): newly diagnosed therapy-related AML (t-AML) or AML with myelodysplasia-related changes (AML-MRC). The EMA approved Vyxeos® in 2018.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Daunorubicin's cytotoxic action is due to its ability to cause DNA damage. The DNA damage is caused by several mechanisms, including intercalation in to DNA, strand breakage and inhibition of topoisomerase II. The DNA damage results in cell death.
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