Cyclophosphamide

Diagram of the molecular structure of Cyclophosphamide
Brand name: Cytoxan®
IUPAC: N,N-bis(2-chloroethyl)-2-oxo-1-oxa-3-aza-2$l^{5}-phosphacyclohexan-2-amine
FDA approval: Yes
Manufacturer Link
Usage:

Cyclophosphamide (Cytoxan®, Neosar®, Cytoxan®IV, Procytox®) is an alkylating agentA chemical that is able to transfer small hydrocarbons to other molecules. They can cause mutations due to their ability to modify nucleotides in DNA. used singly or as part of a combination to treat a wide variety of neoplastic diseases. Malignancies for which cyclophosphamide is used include: Burkitt's lymphomaA cancer arising in the lymphatic system. The white blood cells affected are part of the body's immune system. The lymphatic system is a large network of vessels that carry fluid and cells of the immune system around the body. Lymph nodes are regional collection centers in the lymphatic system. See also, 'lymphatic system'., Bladder cancer, Bone cancer, Cervical cancer, EndometrialRefers to the endometrium, the inner lining of the uterus. The endometrium is a common site of cancer. cancer, Lung cancer and Prostate cancer, Testicular cancer and Cancer of the adrenal cortex. Cyclophosphamide may be administered orally, in the form of an oral solution or tablets, or through injections.1

Mechanism:

Cyclophosphamide is activated by liver cytochromes, which form cross-links with 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. and results in inhibition of DNA synthesis and function.1

The molecular structure below shows the 3 D conformer Cyclophosphamide.

Side effects:

Common side effects include: hair loss (alopecia), nausea and vomiting, diarrhea, depression of blood cell counts, loss of appetite, irritation of the bladder, cough, fever and/or chills, lower back or side pain, as well as skin and mouth ulcers. Less common side effects and toxicities include effects on the germ cells resulting in amenorrhea (cessation of menstrual periods) testicular atrophy, and sterility. For these reasons patients considering cyclophosphamide therapy should talk to their doctor about the drug's effects on fertility, potential or current pregnancy, and breast-feeding. Secondary cancers may appear years after cyclphosphamide therapy. Before beginning treatment with cyclophosphamide patients should discuss all other current medications with their physician.1

  • 1.a. b. Chu, E., & DeVita, V. T. (2015). Physicians' cancer chemotherapy drug manual 2015. Burlington, MA: Jones & Bartlett Learning.
  • 2. Cytoxan.. Prescribing Information. Bristol-Myers Squibb. 2016. [http://www.bms.com]