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Cyclophosphamide information


Cyclophosphamide
Clinical data
Pronunciation/ˌsklˈfɒsfəˌmd, -lə-/[1][2]
Trade namesLyophilized Cytoxan, Endoxan, Cytoxan, Neosar, Procytox, Revimmune, Cycloblastin
AHFS/Drugs.comMonograph
MedlinePlusa682080
Pregnancy
category
  • AU: D
Routes of
administration
By mouth, by injection into a vein
ATC code
  • L01AA01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability>75% (by mouth)
Protein binding>60%
MetabolismLiver
Elimination half-life3–12 hours
ExcretionKidney
Identifiers
IUPAC name
  • (RS)-N,N-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
CAS Number
  • 50-18-0 checkY
PubChem CID
  • 2907
DrugBank
  • DB00531 checkY
ChemSpider
  • 2804 checkY
UNII
  • 6UXW23996M
KEGG
  • D07760 checkY
ChEBI
  • CHEBI:4027 checkY
ChEMBL
  • ChEMBL88 checkY
CompTox Dashboard (EPA)
  • DTXSID5020364 Edit this at Wikidata
ECHA InfoCard100.000.015 Edit this at Wikidata
Chemical and physical data
FormulaC7H15Cl2N2O2P
Molar mass261.08 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point2 °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) checkY
  • Key:CMSMOCZEIVJLDB-UHFFFAOYSA-N checkY
  (verify)

Cyclophosphamide (CP), also known as cytophosphane among other names,[3] is a medication used as chemotherapy and to suppress the immune system.[4] As chemotherapy it is used to treat lymphoma, multiple myeloma, leukemia, ovarian cancer, breast cancer, small cell lung cancer, neuroblastoma, and sarcoma.[4] As an immune suppressor it is used in nephrotic syndrome, granulomatosis with polyangiitis, and following organ transplant, among other conditions.[4][5] It is taken by mouth or injection into a vein.[4]

Most people develop side effects.[4] Common side effects include low white blood cell counts, loss of appetite, vomiting, hair loss, and bleeding from the bladder.[4] Other severe side effects include an increased future risk of cancer, infertility, allergic reactions, and pulmonary fibrosis.[4] Cyclophosphamide is in the alkylating agent and nitrogen mustard family of medications.[4] It is believed to work by interfering with the duplication of DNA and the creation of RNA.[4]

Cyclophosphamide was approved for medical use in the United States in 1959.[4] It is on the World Health Organization's List of Essential Medicines.[6]

  1. ^ "cyclophosphamide – definition of cyclophosphamide in English from the Oxford dictionary". OxfordDictionaries.com. Archived from the original on August 25, 2012. Retrieved 2016-01-20.
  2. ^ "cyclophosphamide". Merriam-Webster.com Dictionary.
  3. ^ "NCI Drug Dictionary". National Cancer Institute. 2 February 2011. Archived from the original on 25 April 2015. Retrieved 20 December 2016.
  4. ^ a b c d e f g h i j "Cyclophosphamide". The American Society of Health-System Pharmacists. Archived from the original on 2 January 2017. Retrieved 8 December 2016.
  5. ^ Pagnoux C (September 2016). "Updates in ANCA-associated vasculitis". European Journal of Rheumatology. 3 (3): 122–133. doi:10.5152/eurjrheum.2015.0043. PMC 5058451. PMID 27733943.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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Cyclophosphamide

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Cyclophosphamide (CP), also known as cytophosphane among other names, is a medication used as chemotherapy and to suppress the immune system. As chemotherapy...

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Granulomatosis with polyangiitis

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combination of immunosuppressive medications such as rituximab or cyclophosphamide and high-dose corticosteroids to control the symptoms of the disease...

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Chemotherapy

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non-classical alkylating agents. Nitrogen mustards include mechlorethamine, cyclophosphamide, melphalan, chlorambucil, ifosfamide and busulfan. Nitrosoureas include...

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Adjuvant therapy

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Doxorubicin and cyclophosphamide Doxorubicin and cyclophosphamide followed by docetaxel Doxorubicin and cyclophosphamide followed by cyclophosphamide, methotrexate...

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Mesna

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brand name Mesnex among others, is a medication used in those taking cyclophosphamide or ifosfamide to decrease the risk of bleeding from the bladder. It...

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Leukemia

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forms of combination chemotherapy (cyclophosphamide, doxorubicin, vincristine, prednisone CHOP, cyclophosphamide, vincristine, prednisone [COP], vincristine...

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Lupus nephritis

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intravenous cyclophosphamide with corticosteroids, and the immune suppressant azathioprine with corticosteroids. MMF and cyclophosphamide with corticosteroids...

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Avacopan

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In the European Union, avacopan, in combination with a rituximab or cyclophosphamide regimen, is indicated for the treatment of adults with severe, active...

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Chemotherapy regimen

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AC doxorubicin (Adriamycin), cyclophosphamide breast cancer BACOD bleomycin, doxorubicin (Adriamycin), cyclophosphamide, vincristine (Oncovin), dexamethasone...

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Perfosfamide

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Perfosfamide is an oxazaphosphorine compound, similar to mafosfamide and cyclophosphamide. Like those compounds it, is metabolized to 4-hydroxycyclophosphamide...

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Scleroderma

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tetracycline antibiotics such as tetracycline Interstitial lung disease with cyclophosphamide, azathioprine with or without corticosteroids Pulmonary arterial hypertension...

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Lupus

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intermittent cytotoxic drugs. These drugs include cyclophosphamide and mycophenolate. Cyclophosphamide increases the risk of developing infections, pancreas...

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Vasculitis

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used. Additionally, other immune suppression medications, such as cyclophosphamide and others, are considered. In case of an infection, antimicrobial...

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Omeprazole

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Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA (prasterone) Efavirenz Ellagic acid Griseofulvin...

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Carboxycyclophosphamide

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metabolite of the cytotoxic antineoplastic drug cyclophosphamide. In the metabolic pathway of cyclophosphamide inactivation it first metabolizes to 4-hydroxycyclophosphamide...

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Hypersensitivity

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and hydroxychloroquine, azathioprine, methotrexate, mycophenolate, cyclophosphamide, low dose IL-2, intravenous immunoglobulins, and belimumab. Omalizumab...

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Systemic scleroderma

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replacement therapy. Active alveolitis is often treated with pulses of cyclophosphamide, often together with a small dose of steroids. The benefit of this...

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Erythromycin

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Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA (prasterone) Efavirenz Ellagic acid Griseofulvin...

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Aplastic anemia

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ciclosporin to modulate the immune system. Chemotherapy with agents such as cyclophosphamide may also be effective but is more toxic than ATG. Antibody therapy...

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Organophosphorus chemistry

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known, one medically significant example being the anti-cancer drug cyclophosphamide. Also derivatives containing the thiophosphoryl group (P=S) include...

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Dactinomycin

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chemotherapy regimens, like the VAC regimen (with vincristine and cyclophosphamide) for treating rhabdomyosarcoma and Ewing's sarcoma. It is also used...

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Fenbendazole

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Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA (prasterone) Efavirenz Ellagic acid Griseofulvin...

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Hemorrhagic cystitis

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hematuria, and hemorrhage. The disease can occur as a complication of cyclophosphamide, ifosfamide and radiation therapy. In addition to hemorrhagic cystitis...

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