cyclophosphamide

Ligand id: 7154

Name: cyclophosphamide

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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
Search UniChem for chemical match using the InChIKey CMSMOCZEIVJLDB-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone CMSMOCZEIVJLDB
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).