Daunorubicin
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| Daunorubicin
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| 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 | |
| ATC code | L01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C27H29NO10 |
| Mol. mass | 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 |
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Overview
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 daunosamine 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 11o, 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]
References
- ↑ Mortensen, ME et al (1992). "Inadvertent intrathecal injection of daunorubicin with fatal outcome". Med Pediatr Oncol 20 (3): 249–253.
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