Doxorubicin

Doxorubicin

Clinical data
Pronunciation	/ˌdɒksəˈruːbᵻsɪn/
Trade names	Adriamycin, Doxil, Caelyx, Myocet, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682221
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	intravenous, intravesical
ATC code	L01DB01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	5% (by mouth)
Protein binding	75%
Metabolism	Liver
Biological half-life	Triphasic; 12 minutes, 3.3 hours, 30 hours. Mean: 1-3 hours
Excretion	Urine (5-12%), faeces (40-50%)
Identifiers
IUPAC name (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
CAS Number	23214-92-8 Y
PubChem (CID)	31703
IUPHAR/BPS	7069
DrugBank	DB00997 Y
ChemSpider	29400 Y
UNII	80168379AG Y
KEGG	D03899 Y
ChEBI	CHEBI:28748 Y
ChEMBL	CHEMBL53463 N
ECHA InfoCard	100.041.344
Chemical and physical data
Formula	C27H29NO11
Molar mass	543.52 g/mol
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)CO)O)N)O
InChI InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27 (36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23 (32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15, 17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1 N Key:AOJJSUZBOXZQNB-TZSSRYMLSA-N Y
NY (what is this?)

Doxorubicin, sold under the trade names Adriamycin among others, is a chemotherapy medication used to treat cancer. This includes breast cancer, bladder cancer, Kaposi's sarcoma, lymphoma, and acute lymphocytic leukemia. It is often used together with other chemotherapy agents. Doxorubicin is given by injection into a vein.

Common side effects include hair loss, bone marrow suppression, vomiting, rash, and inflammation of the mouth. Other serious side effects may include allergic reactions such as anaphylaxis, heart damage, tissue damage at the site of injection, radiation recall, and treatment-related leukemia. People often experience red discoloration of the urine for a few days. Doxorubicin is in the anthracycline and antitumor antibiotic family of medications. Its works in part by interfering with the function of DNA.

Doxorubicin was approved for medical use in the United States in 1974. 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 3.88 to 32.79 USD per 50 mg vial. In the United Kingdom this amount costs the NHS about £92.70. Versions that are pegylated and in liposomes are also available; however, are more expensive. Doxorubicin was originally made from the bacteria Streptomyces peucetius.