cyclophosphamide

bgcolor="#ffffff" align="center" colspan="2" \| Cyclophosphamide chemical structure Cyclophosphamide
align="center" colspan="2" \| N,N-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
CAS number 50-18-0	ATC code L01AA01
bgcolor="#eeeeee" \| Chemical formula	bgcolor="#ddeeff" \| CHCNOP
bgcolor="#eeeeee" \| Molecular weight	bgcolor="#ddeeff" \| 261.087
bgcolor="#eeeeee" \| Bioavailability	bgcolor="#ddeeff" \| ?
bgcolor="#eeeeee" \| Metabolism	bgcolor="#ddeeff" \| hepatic
bgcolor="#eeeeee" \| Elimination half-life	bgcolor="#ddeeff" \| ?
bgcolor="#eeeeee" \| Excretion	bgcolor="#ddeeff" \| ?
bgcolor="#eeeeee" \| Pregnancy category	bgcolor="#ddeeff" \| ?
bgcolor="#eeeeee" \| Legal status	bgcolor="#ddeeff" \| ?
bgcolor="#eeeeee" \| Routes of administration	bgcolor="#ddeeff" \| oral, intravenous

Cyclophosphamide is a nitrogen mustard alkylating agent, used to treat various types of cancer and some autoimmune disorders. It is a "prodrug"; it is converted in the liver to active forms that have chemotherapeutic activity.

Uses

The main use of cyclophosphamide is together with other chemotherapy agents in the treatment of lymphomas, some forms of leukemia and some solid tumors. In addition, its use is becoming more common in autoimmune diseases where disease-modifying antirheumatic drugs (DMARDs) have been ineffective. Systemic lupus erythematosus (SLE) with severe lupus nephritis, for example, may respond to pulsed cyclophosphamide.

Metabolism

Cyclophosphamide is converted by mixed function oxidase enzymes in the liver to active metabolites. The main active metabolite is 4-hydroxycyclophosphamide. 4-hydroxycyclophosphamide exists in equilibrium with its tautomer, aldophosphamide. Most of the aldophosphamide is oxidised to make carboxyphosphamide. A small proportion of aldophosphamide is converted into phosphoramide mustard and acrolein. Acrolein is toxic to the bladder epithelium and can lead to hemorrhagic cystitis.

Side-effects

Side-effects include chemotherapy-induced nausea and vomiting (CINV), bone marrow suppression, alopecia (hair loss) and lethargy. Hemorrhagic cystitis is a frequent complication, but this is prevented by adequate fluid intake and mesna (sodium 2-mercaptoethane sulfonate). Mesna is a sulfhydryl donor and binds acrolein. Cyclophosphamide is itself carcinogenic, potentially causing transitional cell carcinoma of the bladder as a long-term complication.

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