Epirubicin

Diagram of the molecular structure of Epirubicin
Brand name: Ellence®
IUPAC: (7S,9S)-7-[(2R,4S,5R,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
FDA approval: Yes
Usage:

Epirubicin is used to treat breast cancers with lymph node involvement after the tumor is removed (resected), as well as metastaticThe term for a cancer that has spread beyond its point of origin. Metastatic disease is responsible for the majority of cancer deaths. gastric cancer. Epirubicin is administered as an intravenous infusion.1 

Mechanism:

Epirubicin (a derivative of Doxorubicin) is an anthracycline antibiotic that affects cancer cells in two different ways.The drug wedges in DNAAbbreviation for deoxyribonucleic acid. Composed of very long strings of nucleotides, which are abbreviated as A, C, G and T. DNA is the storage form of our genetic material. All of the instructions for the production of proteins are encoded in our DNA. (intercalates). This stops the DNA from being copied (replicationThe process by which DNA is duplicated. DNA replication occurs during the S phase (synthesis) of the cell cycle. Many chemotherapy drugs act during DNA replication. Some are incorporated into the newly replicated DNA and cause problems. Others interfere with enzymes necessary for DNA replication. See topoisomerase.) and/or being used to make proteins (synthesis). The drug inhibits the activity of an enzymeA protein that speeds up the process of chemical reactions in the body without becoming altered in the process. Almost every biological process is driven by the activity of enzymes. Without enzyme catalysts, the complex reactions that build and break down cell parts would not happen at a rate compatible with life. Enzyme names usually describe the reaction that is being catalyzed and all of them end in -ase., topoisomeraseAn enzyme that cuts double stranded DNA to reduce tension created during local unwinding of the helix. Unwinding of DNA is required for transcription, translation and replication. Chemotherapy drugs such as topotecan and etoposide (VP-16) inhibit topoisomerases. type II, which leads to breaks in the DNA.1

The molecule above shows the 3D conformer structure of Epirubicin.

 

Side effects:

Common side effects include nausea and vomiting, fatigue, hair loss, mouth sores. Epirubicin may cause blood cell counts to decrease. Patients should have blood tests before each treatment cycle to monitor this. Patients may also take an antibiotic during treatment to prevent infections. Epirubicin may cause more serious delayed side effects which include heart problems or acute myelogenous leukemiaA cancer affecting the cells that develop into white or red blood cells. Both of these cell types originate from stem cells in bone marrow. Red blood cells function to carry oxygen to our tissues and the white cells (leukocytes) are part of our immune system. The cancerous cells often accumulate in the blood.. However, these serious effects are rare.1

Contraindications:

Epirubicin should not be taken by women who are pregnant and patients should not become pregnant while using this drug, as it may have harmful affects on the developing fetus. This drug may have effects on fertility after treatment has ended.1

  • 1.a. b. c. d. Chu, E., & DeVita, V. T. (2015). Physicians' cancer chemotherapy drug manual 2015. Burlington, MA: Jones & Bartlett Learning.