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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:06 UTC
HMDB IDHMDB0014672
Secondary Accession Numbers
  • HMDB14672
Metabolite Identification
Common NameCyclophosphamide
DescriptionCyclophosphamide, also known as cytoxan or cytophosphan, belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom. 3) the induction of mispairing of the nucleotides leading to mutations. Cyclophosphamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Its side effect, alopecia, has been used for defleecing sheep. Within humans, cyclophosphamide participates in a number of enzymatic reactions. In particular, cyclophosphamide can be converted into 4-hydroxycyclophosphamide; which is mediated by the enzymes cytochrome P450 2C9, cytochrome P450 2B6, cytochrome P450 2C19, cytochrome P450 3A4, cytochrome P450 2C8, and cytochrome P450 2A6. In addition, cyclophosphamide can be converted into chloroacetaldehyde and 3-dechloroethylifosfamide through the action of the enzyme cytochrome P450 3A4. In humans, cyclophosphamide is involved in cyclophosphamide metabolism pathway. It has been used in the treatment of lymphoma and leukemia. Cyclophosphamide is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound.
Structure
Data?1582753206
Synonyms
ValueSource
(+-)-CyclophosphamideChEBI
(RS)-CyclophosphamideChEBI
2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxideChEBI
Bis(2-chloroethyl)phosphoramide cyclic propanolamide esterChEBI
Cyclophosphamide anhydrousChEBI
N,N-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxideChEBI
CytoxanKegg
Cyclophosphamide monohydrateHMDB
CytophosphanHMDB
SendoxanHMDB
Anhydrous, cyclophosphamideHMDB
Cyclophosphamide, (S)-isomerHMDB
CyclophosphaneHMDB
CytophosphaneHMDB
EndoxanHMDB
NeosarHMDB
Cyclophosphamide, (R)-isomerHMDB
Monohydrate, cyclophosphamideHMDB
ProcytoxHMDB
(+,-)-2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide monohydrateMeSH
Chemical FormulaC7H15Cl2N2O2P
Average Molecular Weight261.086
Monoisotopic Molecular Weight260.02481966
IUPAC Name2-[bis(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one
Traditional Name2-[bis(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one
CAS Registry Number6055-19-2
SMILES
ClCCN(CCCl)P1(=O)NCCCO1
InChI Identifier
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
InChI KeyCMSMOCZEIVJLDB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrogen mustard compounds. Nitrogen mustard compounds are compounds having two beta-haloalkyl groups bound to a nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassNitrogen mustard compounds
Direct ParentNitrogen mustard compounds
Alternative Parents
Substituents
  • Nitrogen mustard
  • Phosphoric monoester diamide
  • Organic phosphoric acid derivative
  • Oxazaphosphinane
  • Organic phosphoric acid amide
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organochloride
  • Organopnictogen compound
  • Organohalogen compound
  • Organic oxygen compound
  • Alkyl chloride
  • Alkyl halide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Environmental role:

Industrial application:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point41 - 45 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility15.1 g/LNot Available
LogP0.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility15.1 g/LALOGPS
logP0.76ALOGPS
logP0.097ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)13.43ChemAxon
pKa (Strongest Basic)0.084ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.48 m³·mol⁻¹ChemAxon
Polarizability23.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-2930000000-a5e2529d99bd261703f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0059-1490000000-36d8ebdb421248c38c7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-1390000000-b8dc1a824ec33e388213Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0390000000-66983035d1db7ac36bd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001l-0970000000-939110a705ed71803ab8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-2bdfe4296c2bdf8d4a99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0190000000-1e8e017f8e39fa5d73cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0930000000-d7459c8d20a8fc59f6f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0900000000-33cb20e845200f9d2618Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-2900000000-09d33a8387b9d152f24aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ox-6900000000-cdebe09ff6df7c25b477Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-d749f27c3144da2c431cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0190000000-a6fa921df18384671a7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0930000000-abdb40162fc8a44200f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0900000000-8c0705ee62a5f9c7d44eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-2900000000-a299026342c77e92c48cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ox-6900000000-fc2845c75bbccc83ad99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001l-0970000000-83e0f5b88b6fbe0a1ea7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0900000000-5490a2b493bfde967fa3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0006-0900000000-456626f46e480e0ac670Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9150000000-28408c9f0486cc7568f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9600000000-fd85ba5646421fb4dd68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-dc67f093f2419f82cb18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1920000000-ef90686fe8c9da71ccd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c974342f3a086d037df6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002u-9600000000-142aeef910da3ef2f6b3Spectrum
MSMass Spectrum (Electron Ionization)splash10-08fr-9470000000-53f4a8ff83c415492e03Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00531 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00531 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00531
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2804
KEGG Compound IDC07888
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclophosphamide
METLIN IDNot Available
PubChem Compound2907
PDB IDNot Available
ChEBI ID4027
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Brock N: Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture. Cancer Res. 1989 Jan 1;49(1):1-7. [PubMed:2491747 ]
  2. Brock N: The history of the oxazaphosphorine cytostatics. Cancer. 1996 Aug 1;78(3):542-7. [PubMed:8697402 ]
  3. (). FDA label . .