General
Preferred name
CYCLOPHOSPHAMIDE
Synonyms
Cyclophosphamide Monohydrate ()
CYCLOPHOSPHAMIDE HYDRATE ()
Clafen (Cyclophosphamide) ()
Cytoxan ()
Neosar ()
Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester ()
Mitoxan ()
Enduxan ()
Endoxan ()
Genoxal ()
Procytox ()
(-)-Cyclophosphamide ()
Cyclophosphamide (hydrate) ()
Cytoxan6055-19-2 ()
Cyclophosphamide (NSC-26271) Monohydrate ()
Cytoxan Monohydrate ()
NSC 26271,Endoxan, Cytoxan, Neosar, Procytox, Revimmune, Cytophosphane ()
Cyclophosphamide ()
Cytophosphane ()
Cytophosphan ()
Cyclostin ()
Ciclofosfamide ()
NSC-26271 ()
Revimmune ()
Endoxana ()
Endoxan monohydrate ()
Cyclophosphamide anhydrous ()
Cytoxan (Lyophilized) ()
Cyclophosphamidum ()
B-518 ()
NSC-756711 ()
Cyclophosphamide hydrate ()
Cycloblastin ()
Cyclophosphamide monohydrate ()
Lyophilized Cytoxan ()
Cyclophosphanum ()
Cyclophosphamide-d4 ()
P&D ID
PD002782
CAS
6055-19-2
50-18-0
60007-95-6
173547-45-0
Tags
prodrug
nuisance
natural product
drug
available
Approved by
PMDA
FDA
First approval
1959
Drug Status
investigational
approved
Drug indication
Antineoplastic
Immunosuppressant
Solid tumour/cancer
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
TOXICITY Adverse reactions reported most often include neutropenia, febrile neutropenia, fever, alopecia, nausea, vomiting, and diarrhea.;
DESCRIPTION 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). (GtoPdb)
DESCRIPTION DNA alkylator (Informer Set)
DESCRIPTION Purine analog; prodrug of 6-mercaptopurine (Cat. No. 4103) (Tocris Bioactive Compound Library)
DESCRIPTION Cancer chemotherapeutic; cross-links DNA (LOPAC library)
DESCRIPTION Low-dose preferentially deplets Treg cells; An alkylating agent of the nitrogen mustard type with antineoplastic and immunosuppressive activities; Phase I-II (BOC Sciences Bioactive Compounds)
Cell lines
12
Organisms
0
Compound Sets
28
AdooQ Bioactive Compound Library
A10224
A11635
BOC Sciences Bioactive Compounds
cyclophosphamide-cas-50-18-0-item-465291
Cayman Chemical Bioactives
13849
22114
ChEMBL Approved Drugs
CHEMBL88
CHEMBL1200796
ChEMBL Drugs
CHEMBL88
CHEMBL1200796
DrugBank
DB00531
DrugBank Approved Drugs
DB00531
DrugCentral
758
DrugCentral Approved Drugs
758
DrugMAP
DM4O2Z7
DrugMAP Approved Drugs
DM4O2Z7
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
7154
Informer Set
32620
JUMP-Target 1 Compound Set
2907
LOPAC library
MedChem Express Bioactive Compound Library
HY-17420
HY-17420A
NIH Approved Oncology Drugs
87150
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Nuisance compounds in cellular assays
ReFrame library
Selleckchem Bioactive Compound Library
Clafen
cyclophosphamide-monohydrate
TargetMol Bioactive Compound Library
T0707
The Spectrum Collection
Tocris Bioactive Compound Library
4091
External IDs
82
Properties
(calculated by RDKit )
Molecular Weight
260.02
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
1
Aromatic Ring Count
0
cLogP
1.88
TPSA
41.57
Fraction CSP3
1.0
Chiral centers
1.0
Largest ring
6.0
QED
0.61
Structural alerts
1
Genotoxic
Nuisance compounds in cellular assays
Related compounds
Custom attributes
(extracted from source data)
Compound status
FDA
Pathway
DNA Damage/DNA Repair
Immunology/Inflammation
Cell Cycle/DNA Damage
Target
DNA
MRP1
CYP2A6
DNA alkylator/crosslinker
DNA alkylator
DNA/RNA Synthesis
Primary Target
Apoptosis Inducers
Member status
member
MOA
DNA alkylating agent prodrug
BCL2 Expression Inhibitors
LGALS1 Expression Inhibitors
Therapeutic Class
Anticancer Agents
Solubility
In water, 1-5 g/100 mL at 23 °C
slightly soluble in benzene, carbon tetrachloride
very slightly soluble in ether and acetone.
Source data