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| Trade names | Cerubidine, others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682289 |
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| Routes of administration | Intravenous |
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| Pharmacokinetic data | |
| Metabolism | Liver |
| Eliminationhalf-life | 26.7hours (metabolite) |
| Excretion | Bile duct and urinary |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.040.048 |
| Chemical and physical data | |
| Formula | C27H29NO10 |
| Molar mass | 527.526 g·mol−1 |
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Daunorubicin, also known asdaunomycin, is achemotherapy medication used to treatcancer.[2] Specifically it is used foracute myeloid leukemia (AML),acute lymphoblastic leukemia (ALL),chronic myelogenous leukemia (CML), andKaposi's sarcoma.[2] It is administered byinjection into a vein.[2] Aliposomal formulation known asliposomal 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 includeheart disease andtissue death at the site of injection.[2] Use inpregnancy may harm the fetus.[2] Daunorubicin is in theanthracycline family of medication.[3] It works in part by blocking the function oftopoisomerase II.[2]
Daunorubicin was approved for medical use in the United States in 1979.[2] It is on theWorld Health Organization's List of Essential Medicines.[4] It was originally isolated from bacteria of theStreptomyces type.[5]
Daunorubicin is used to slow or stops the growth of cancer cells in the body. Treatment is usually performed together with other chemotherapy drugs (such ascytarabine), and its administration depends on the type of tumor and the degree of response.[citation needed][contradictory]
In addition to its major use in treating acute myeloid leukemia, daunorubicin is also used to treatneuroblastoma. Daunorubicin has been used with other chemotherapy agents to treat the blastic phase ofchronic myelogenous leukemia.[citation needed]
Daunorubicin is also used as the starting material for semi-synthetic manufacturing ofdoxorubicin,epirubicin andidarubicin.[citation needed]
Similar todoxorubicin, daunorubicin interacts with DNA byintercalation and inhibition of macromolecularbiosynthesis.[6][7] This inhibits the progression of the enzymetopoisomerase II, which relaxes supercoils in DNA; without action of topoisomerase II, these DNA supercoils interfere intranscription of DNA. Daunorubicin stabilizes the topoisomerase II complex after it has broken the DNA chain for replication, preventing the DNA double helix from being resealed and thereby stopping the process ofreplication.On binding to DNA, daunomycinintercalates, with its daunosamine residue directed toward the minor groove. It has the highest preference for two adjacent G/Cbase pairs flanked on the 5' side by an A/T base pair. Crystallography shows that daunomycin induces a local unwinding angle of 8°, and other conformational disturbances of adjacent and second-neighbour base pairs.[8]It can also inducehistone eviction fromchromatin uponintercalation.[9][10]
In the 1950s, anItalian research company,Farmitalia Research Laboratories, began an organized effort to isolate anticancer compounds from soil-basedmicrobes. A soil sample was isolated from the area surrounding theCastel del Monte, a 13th-century castle inApulia. A new strain ofStreptomyces peucetius which produced a red pigment was isolated, and an antibiotic was produced from this bacterium that was found to have good activity againstmurine tumors. Since a group ofFrench researchers discovered the same compound at about the same time, the two teams named the compound daunorubicin, combining the nameDauni, a pre-Roman tribe that occupied the area of Italy where the compound was isolated, with the French word forruby,rubis, describing the color.[11][12][13] Clinical trials began in the 1960s, and the drug saw success in treating acute leukemia and lymphoma.
However, by 1967, it was recognized that daunorubicin could produce fatal cardiac toxicity.[14]
In 2015–16, a team atOhio State University "showed that, by carefully manipulating strands of viral DNA, an origami structure with complex folds can be created in just 10 minutes. Incredibly, these structures are only 100 nanometers across – that's 1,000 times smaller than the width of a human hair. Small volumes of daunorubicin can be wrapped up in these minuscule pods, which can then be released into a leukemia cell-filled environment."[15][16][unreliable medical source?]
Daunorubicin should only be administered in a rapidintravenous infusion.[contradictory] It should not be administeredintramuscularly orsubcutaneously, since it may cause extensive tissuenecrosis.It should also never be administeredintrathecally (into thespinal canal), as this will cause extensive damage to thenervous system and may lead todeath. Daunorubicin has been used intravitreally (inside the eye) for the purposes of preventing proliferative vitreoretinopathy, a common complication following retinal detachment surgery, but has not been found to be effective and is not used for any other ophthalmic purposes at this time.[17]
