CHEBI:4027 - cyclophosphamide

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ChEBI Name cyclophosphamide
ChEBI ID CHEBI:4027
Definition A phosphorodiamide that is 1,3,2-oxazaphosphinan-2-amine 2-oxide substituted by two 2-chloroethyl groups at the amino nitrogen atom.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C7H15Cl2N2O2P
Net Charge 0
Average Mass 261.08544
Monoisotopic Mass 260.025
InChI InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
InChIKey CMSMOCZEIVJLDB-UHFFFAOYSA-N
SMILES ClCCN(CCCl)P1(=O)NCCCO1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
alkylating agent
Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
(via nitrogen mustard )
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
drug allergen
Any drug which causes the onset of an allergic reaction.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): antirheumatic drug
A drug used to treat rheumatoid arthritis.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
drug allergen
Any drug which causes the onset of an allergic reaction.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cyclophosphamide (CHEBI:4027) has role alkylating agent (CHEBI:22333)
cyclophosphamide (CHEBI:4027) has role antineoplastic agent (CHEBI:35610)
cyclophosphamide (CHEBI:4027) has role antirheumatic drug (CHEBI:35842)
cyclophosphamide (CHEBI:4027) has role carcinogenic agent (CHEBI:50903)
cyclophosphamide (CHEBI:4027) has role drug allergen (CHEBI:88188)
cyclophosphamide (CHEBI:4027) has role environmental contaminant (CHEBI:78298)
cyclophosphamide (CHEBI:4027) has role immunosuppressive agent (CHEBI:35705)
cyclophosphamide (CHEBI:4027) has role xenobiotic (CHEBI:35703)
cyclophosphamide (CHEBI:4027) is a nitrogen mustard (CHEBI:37598)
cyclophosphamide (CHEBI:4027) is a organochlorine compound (CHEBI:36683)
cyclophosphamide (CHEBI:4027) is a phosphorodiamide (CHEBI:35467)
Incoming cyclophosphamide hydrate (CHEBI:4026) has part cyclophosphamide (CHEBI:4027)
IUPAC Name
N,N-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
Synonyms Sources
(+-)-Cyclophosphamide ChemIDplus
(RS)-Cyclophosphamide ChemIDplus
2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide NIST Chemistry WebBook
Bis(2-chloroethyl)phosphoramide cyclic propanolamide ester ChemIDplus
Cyclophosphamide anhydrous KEGG COMPOUND
N,N-bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide IUPAC
Manual Xrefs Databases
758 DrugCentral
C07888 KEGG COMPOUND
Cyclophosphamide Wikipedia
D07760 KEGG DRUG
DB00531 DrugBank
HMDB0014672 HMDB
LSM-4961 LINCS
View more database links
Registry Numbers Types Sources
11744 Beilstein Registry Number Beilstein
11744 Reaxys Registry Number Reaxys
50-18-0 CAS Registry Number KEGG COMPOUND
50-18-0 CAS Registry Number NIST Chemistry WebBook
50-18-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15711186 PubMed citation Europe PMC
7850793 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag