Daunorubicin

Daunorubicin

Clinical data
Trade names	Cerubidine, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682289
Pregnancy category	D (U.S.)
Routes of administration	Exclusively intravenous. Causes severe necrosis if administered intramuscularly or subcutaneously
ATC code	L01DB02 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Metabolism	Liver
Biological half-life	26.7 hours (metabolite)
Excretion	Biliary 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 Y
PubChem CID	30323
IUPHAR/BPS	7063
DrugBank	DB00694 Y
ChemSpider	28163 Y
UNII	ZS7284E0ZP
KEGG	C01907 Y
ChEBI	CHEBI:41977 Y
ChEMBL	CHEMBL178 Y
ECHA InfoCard	100.040.048
Chemical and physical data
Formula	C27H29NO10
Molar mass	527.52 g/mol 563.99 g/mol (HCl salt)
3D model (Jmol)	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 Y Key:STQGQHZAVUOBTE-VGBVRHCVSA-N Y

Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically it is used for acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. It is used 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 baby. Daunorubicin is in the anthracycline family of medication. It works in part by blocking the function of topoisomerase II.

Daunorubicin was approved for medical use in the United States in 1979. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 5.79 to 37.18 USD for a 20 mg vial. This amount in the United Kingdom costs the NHS about 55.00 pounds. It was originally isolated from bacteria of the Streptomyces type.