cyclophosphamide

Ligand id: 7154

Name: cyclophosphamide

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 51.38
Molecular weight 260.02
XLogP 0.84
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (source: FDA (1959))
IUPAC Name
N,N-bis(2-chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine
International Nonproprietary Names
INN number INN
878 cyclophosphamide
Synonyms
cytophosphane
Cytoxan®
Endoxan®
Database Links
CAS Registry No. 50-18-0
ChEMBL Ligand CHEMBL88
DrugBank Ligand DB00531
PubChem CID 2907
Search Google for chemical match using the InChIKey CMSMOCZEIVJLDB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone CMSMOCZEIVJLDB
Search PubMed clinical trials cyclophosphamide
Search PubMed titles cyclophosphamide
Search PubMed titles/abstracts cyclophosphamide
Wikipedia Cyclophosphamide
Comments
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. It is on the World Health Organization's List of Essential Medicines (link to 2015 list).