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.^[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]

^ "Daunorubicin (Cerubidine) Use During Pregnancy". Drugs.com. 19 September 2019. Retrieved 15 August 2020.
^ ^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.
^ British National Formulary: BNF 69 (69th ed.). British Medical Association. 2015. pp. 581–583. ISBN 9780857111562.
^ 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.
^ 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.

[Drugs.com_pregnancy-1] "Daunorubicin (Cerubidine) Use During Pregnancy". Drugs.com. 19 September 2019. Retrieved 15 August 2020.

[AHFS2016-2] ^ ^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.

[BNF69-3] British National Formulary: BNF 69 (69th ed.). British Medical Association. 2015. pp. 581–583. ISBN 9780857111562.

[WHO21st-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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