Article: Daunorubicin

Daunorubicin
Systematic (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
Identifiers
CAS number	20830-81-3
ATC code	L01DB02
PubChem	30323
DrugBank	APRD00521
Chemical data
Formula	C27H29NO10
Mol. weight	527.52 g/mol 563.99 g/mol (HCl salt)
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Half life	26.7 hours (metabolite)
Excretion	Biliary and urinary
Therapeutic considerations
Pregnancy cat.	D (U.S.)
Legal status
Routes	Exclusively intravenous. Causes severe necrosis if administered intramuscularly or subcutaneously

Daunorubicin or daunomycin (daunomycin cerubidine) is chemotherapy of the anthracycline family that is given as a treatment for some types of cancer. It is most commonly used to treat specific types of leukaemia (acute myeloid leukemia and acute lymphocytic leukemia). It was initially isolated from Streptomyces peucetius.

Uses

It slows or stops the growth of cancer cells in the body. Treatment is usually together with other chemotherapy drugs (such as cytarabine), and its administration depends on the type of tumor and the degree of response.

In addition to its major use in treating AML, daunorubicin is also used to treat neuroblastoma. Daunorubicin has been used with other chemotherapy agents to treat the blastic phase of chronic myelogenous leukemia.

Mode of action

On binding to DNA, daunomycin intercalates, with its duanosamine residue directed toward the minor groove. It has the highest preference for two adjacent G/C base pairs flanked on the 5' side by an A/T base pair. Daunomycin effectively binds to every 3 base pairs and induces a local unwinding angle of 11^o, but negligible distortion of helical conformation.

Route of administration

Daunorubicin should only be administered in a rapid intravenous infusion. It should not be administered intramuscularly or subcutaneously, since it may cause extensive tissue necrosis. It should also never be administered intrathecally (into the spinal canal), as this will cause extensive damage to the nervous system and may lead to death^[1]

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