|Cyclopropane||Cyclopropyl Methyl Ether||Cyclorphan||Cycloserine||Cyclosporins|
|Systematic (IUPAC) name|
|Pregnancy cat.||D (AU) D (US)|
|Legal status||℞ Prescription only|
|Mol. mass||261.086 g/mol|
|Melt. point||2 °C (36 °F)|
|(what is this?)|
Cyclophosphamide (INN, trade names Endoxan, Cytoxan, Neosar, Procytox, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazaphosphinans group.
An alkylating agent adds an alkyl group (CnH2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. This interferes with DNA replication by forming intrastrand and interstrand DNA crosslinks.
It is used to treat cancers and autoimmune disorders. As a prodrug, it is converted in the liver to active forms that have chemotherapeutic activity.
Cyclophosphamide has severe and life-threatening adverse effects, including acute myeloid leukemia, bladder cancer, hemorrhagic cystitis, and permanent infertility, especially at higher doses. For autoimmune diseases, doctors often substitute less-toxic methotrexate or azathioprine after an acute crisis.