Daunorubicin

Daunorubicin
Clinical data
Trade names	Cerubidine, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682289
Pregnancy; category	AU: D;
Routes of; administration	Intravenous
ATC code	L01DB02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only;
Pharmacokinetic data
Metabolism	Liver
Elimination half-life	26.7 hours (metabolite)
Excretion	Bile 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 ;
PubChem CID	30323;
IUPHAR/BPS	7063;
DrugBank	DB00694 ;
ChemSpider	28163 ;
UNII	ZS7284E0ZP;
KEGG	C01907 ;
ChEBI	CHEBI:41977 ;
ChEMBL	ChEMBL178 ;
CompTox Dashboard (EPA)	DTXSID7022883 ;
ECHA InfoCard	100.040.048
Chemical and physical data
Formula	C27H29NO10
Molar mass	527.526 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 ; Key:STQGQHZAVUOBTE-VGBVRHCVSA-N ;
	(verify)

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.

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

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