File:Cyclophosphamide.svg · Wikimedia Commons · See Wikimedia Commons
(RS)-cyclophosphamide
Sign in to saveAlso known as cytophosphane, N,N-bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide, 2-[bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide, bis(2-chloroethyl)phosphoramide cyclic propanolamide ester, (+-)-cyclophosphamide, anhydrous cyclophosphamide, cyclophosphamide anhydrous, cyclophosphamide
Cyclophosphamide (CP), also known as cytophosphane among other names, 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, neuroblastoma, and sarcoma. As an immune suppressor it is used in nephrotic syndrome, ANCA-associated vasculitis, and following organ transplant, among other conditions. It is taken by mouth or injection into a vein.
Chemical data
- Formula
- C7H15Cl2N2O2P
- Molecular weight
- 261.08 g/mol
- IUPAC name
- N,N-bis(2-chloroethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
- SMILES
- C1CNP(=O)(OC1)N(CCCl)CCCl
- InChIKey
- CMSMOCZEIVJLDB-UHFFFAOYSA-N
- XLogP
- 0.6
- Polar surface area
- 41.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
86,872 papers- Cyclophosphamide and cancer: golden anniversary.Nature reviews. Clinical oncology · 2009
- The effect of cyclophosphamide on the immune system: implications for clinical cancer therapy.Cancer chemotherapy and pharmacology · 2016
- Cyclophosphamide in dermatology.The Australasian journal of dermatology · 2017
- Cyclophosphamide cardiotoxicity.The National medical journal of India · 1992
- West German Study PlanB Trial: Adjuvant Four Cycles of Epirubicin and Cyclophosphamide Plus Docetaxel Versus Six Cycles of Docetaxel and Cyclophosphamide in HER2-Negative Early Breast Cancer.Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 2019
via PubMed
Wikidata facts
- Mass
- 260.02482
Show 3 more facts
- chemical formula
- C₇H₁₅Cl₂N₂O₂P
- canonical SMILES
- C1CNP(=O)(OC1)N(CCCl)CCCl
- Commons category
- Cyclophosphamide
Sources (7)
via Wikidata · CC0
~14 min read
Article
18 sectionsContents
- Medical uses
- Cancer
- Autoimmune diseases
- AL amyloidosis
- Graft-versus-host disease
- Contraindications
- Side effects
- Bladder bleeding
- Infection
- Infertility
- Cancer
- Pharmacology
- Mechanism of action
- History
- Society and culture
- Research
- References
- External links
Cyclophosphamide (CP), also known as cytophosphane among other names, 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, neuroblastoma, and sarcoma. As an immune suppressor it is used in nephrotic syndrome, ANCA-associated vasculitis, and following organ transplant, among other conditions. 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 is believed to work by interfering with the duplication of DNA and the creation of RNA.