cyclophosphamide   Click here for help

GtoPdb Ligand ID: 7154

Synonyms: cytophosphane | Cytoxan® | Endoxan®
Approved drug
cyclophosphamide is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Cyclophosphamide is an alkylating agent of the nitrogen mustard type. It is converted in vivo to the active metabolite 4-hydroxy cyclophosphamide by liver cytochrome P450 (CYP) enzymes. It is used mainly as a cancer chemotherapeutic. It can be used to treat autoimmune conditions, but as it has severe and life-threatening side-effects, other less toxic medications may be the preferred option following an acuteautoimmune crisis.
Cyclophosphamide is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 51.38
Molecular weight 260.02
XLogP 0.83
No. Lipinski's rules broken 0
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InChI InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
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Summary of Clinical Use Click here for help
Used as an antineoplastic agent to treat various malignancies. This drug is also used to treat certain cases of pediatric nephrotic syndrome (kidney disease) and as an immunosuppressant to control rejection following organ or bone marrow transplantation..
Mechanism Of Action and Pharmacodynamic Effects Click here for help
As a DNA alkylating (cross-linking) agent, cyclophosphamide treatment irreversibly interferes with DNA replication, RNA transcription and general disruption of nucleic acid function. This action causes cell death. Due to the complex and varied nature of nucleic acids we do not include DNA or RNA as targets on this database.
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