Cyclophosphamide

Cyclophosphamide
Clinical data


Pronunciation	/ˌsaɪkloʊˈfɒsfəˌmaɪd, -lə-/
Trade names	Lyophilized Cytoxan, Endoxan, Cytoxan, Neosar, Procytox, Revimmune, Cycloblastin
AHFS/Drugs.com	Monograph
MedlinePlus	a682080
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	by mouth, intravenous
ATC code	L01AA01 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	>75% (by mouth)
Protein binding	>60%
Metabolism	Liver
Biological half-life	3–12 hours
Excretion	Kidney
Identifiers
IUPAC name (RS)-N,N-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
CAS Number	50-18-0^Y
PubChem (CID)	2907
DrugBank	DB00531^Y
ChemSpider	2804^Y
UNII	6UXW23996M^Y
KEGG	D07760^Y
ChEBI	CHEBI:4027^Y
ChEMBL	CHEMBL88^Y
ECHA InfoCard	100.000.015
Chemical and physical data
Formula	C₇H₁₅Cl₂N₂O₂P
Molar mass	261.086 g/mol
3D model (Jmol)	Interactive image
Melting point	2 °C (36 °F)
SMILES O=P1(OCCCN1)N(CCCl)CCCl
InChI InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)^Y Key:CMSMOCZEIVJLDB-UHFFFAOYSA-N^Y

Cyclophosphamide (CP), also known as cytophosphane among other, is a medication used as chemotherapy and to suppress the immune system. As chemotherapy it is used to treat lymphoma, multiple myeloma, leukemia, ovarian cancer, breast cancer, small cell lung cancer, and sarcoma. As an immune suppressor it is used in nephrotic syndrome and following organ transplant. It is taken by mouth or injection into a vein.

Most people develop side effects. Common side effects include low white blood cell counts, loss of appetite, vomiting, hair loss, and bleeding from the bladder. Other severe side effects include an increased future risk of cancer, infertility, allergic reactions, and pulmonary fibrosis. Cyclophosphamide is in the alkylating agent and nitrogen mustard family of medications. It works by interfering with the duplication of DNA and the creation of RNA.

Cyclophosphamide was approved for medical use in the United States in 1959. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 3.65 to 14.30 USD per 1 g vial. In the United Kingdom this dose costs the NHS about 17.06 pounds. In the United States this dose by mouth is about 19.56 USD.

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Wikipedia