CHEBI:196991 - 4-hydroperoxycyclophosphamide

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ChEBI Name 4-hydroperoxycyclophosphamide
ChEBI ID CHEBI:196991
Definition A phosphorodiamide that is the active metabolite of the nitrogen mustard cyclophosphamide. It has potent antineoplastic and immunosuppressive properties.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C7H15Cl2N2O4P
Net Charge 0
Average Mass 293.08500
Monoisotopic Mass 292.01465
InChI InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13)
InChIKey VPAWVRUHMJVRHU-UHFFFAOYSA-N
SMILES OOC1CCOP(=O)(N1)N(CCCl)CCCl
Roles Classification
Biological Role(s): 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.
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 )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
drug allergen
Any drug which causes the onset of an allergic reaction.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 4-hydroperoxycyclophosphamide (CHEBI:196991) has role alkylating agent (CHEBI:22333)
4-hydroperoxycyclophosphamide (CHEBI:196991) has role antineoplastic agent (CHEBI:35610)
4-hydroperoxycyclophosphamide (CHEBI:196991) has role drug allergen (CHEBI:88188)
4-hydroperoxycyclophosphamide (CHEBI:196991) has role immunosuppressive agent (CHEBI:35705)
4-hydroperoxycyclophosphamide (CHEBI:196991) has role metabolite (CHEBI:25212)
4-hydroperoxycyclophosphamide (CHEBI:196991) is a nitrogen mustard (CHEBI:37598)
4-hydroperoxycyclophosphamide (CHEBI:196991) is a organochlorine compound (CHEBI:36683)
4-hydroperoxycyclophosphamide (CHEBI:196991) is a peroxol (CHEBI:35924)
4-hydroperoxycyclophosphamide (CHEBI:196991) is a phosphorodiamide (CHEBI:35467)
IUPAC Name
2-[bis(2-chloroethyl)amino]-2-oxido-1,3,2-oxazaphosphinan-4-yl hydroperoxide
Synonyms Sources
2-(Bis(2-chloroethyl)amino)-4-hydroperoxytetrahydro-2H-1,3,2-oxazaphosphorine ChemIDplus
2-(bis(2-chloroethyl)amino)tetrahydro-2-oxideo-2H-1,3,2-oxazaphosphorin-4-yl hydroperoxide ChemIDplus
4-Hydroperoxycyclofosfamide ChemIDplus
4-OOH Cyclophosphamide ChemIDplus
Perfosfamide (unspecified) ChemIDplus
Manual Xrefs Databases
NL7208895 Patent
US3808297 Patent
View more database links
Registry Numbers Types Sources
39800-16-3 CAS Registry Number ChemIDplus
531579 Reaxys Registry Number Reaxys
531579 Beilstein Registry Number Beilstein
Citation Waiting for Citations Type Source
8024619 PubMed citation Europe PMC
Last Modified
04 March 2019