Melphalan

A chemotherapy drug used to treat multiple myeloma and ovarian cancer

Chemical structure of Melphalan

Melphalan, also known by its brand name Alkeran, is a chemotherapy medication used primarily in the treatment of multiple myeloma and ovarian cancer. It belongs to the class of drugs known as alkylating agents, which work by interfering with the DNA replication process in cancer cells, ultimately leading to cell death.

Medical Uses

Melphalan is primarily used in the treatment of multiple myeloma, a type of cancer that affects plasma cells in the bone marrow. It is also used in the treatment of ovarian cancer, particularly in cases where the cancer has not responded to other treatments. Additionally, melphalan may be used in high-dose regimens as part of a conditioning regimen prior to hematopoietic stem cell transplantation.

Multiple Myeloma

In the treatment of multiple myeloma, melphalan is often used in combination with other drugs such as prednisone or dexamethasone. It can be administered orally or intravenously, depending on the specific treatment protocol. The drug works by cross-linking DNA strands, which prevents the cancer cells from dividing and growing.

Ovarian Cancer

For ovarian cancer, melphalan is typically used when the cancer has recurred or is resistant to other forms of chemotherapy. It is administered intravenously and may be used in combination with other chemotherapeutic agents to enhance its effectiveness.

Mechanism of Action

Melphalan is an alkylating agent that forms covalent bonds with DNA, leading to the formation of cross-links between DNA strands. This cross-linking inhibits DNA replication and transcription, ultimately triggering apoptosis, or programmed cell death, in rapidly dividing cancer cells. The drug is particularly effective against cells that are in the S phase of the cell cycle, where DNA synthesis occurs.

Ball-and-stick model of Melphalan

Side Effects

Common side effects of melphalan include nausea, vomiting, diarrhea, and bone marrow suppression, which can lead to anemia, leukopenia, and thrombocytopenia. Patients receiving melphalan are at increased risk of infections due to the suppression of white blood cell production. Long-term use of melphalan has been associated with an increased risk of developing secondary malignancies, such as acute myeloid leukemia.

Pharmacokinetics

Melphalan is absorbed variably when administered orally, with bioavailability ranging from 25% to 89%. It is extensively metabolized in the liver and excreted primarily in the urine. The drug has a half-life of approximately 1.5 hours when administered intravenously.

Synthesis

The synthesis of melphalan involves the reaction of L-phenylalanine with bis(2-chloroethyl)amine, resulting in the formation of the active compound. This process highlights the drug's structural similarity to the amino acid phenylalanine, which allows it to be preferentially taken up by rapidly dividing cells.

Synthesis of Melphalan

Related Pages

• Chemotherapy
• Alkylating agent
• Multiple myeloma
• Ovarian cancer