CHEBI:5864 - ifosfamide

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ifosfamide
ChEBI ID CHEBI:5864
Definition The simplest member of the class of ifosfamides that is 1,3,2-oxazaphosphinan-2-amine 2-oxide substituted by 2-chloroethyl groups on both the nitrogen atoms respectively. It is a nitrogen mustard alkylating agent used in the treatment of advanced breast cancer.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:219640
Supplier Information No supplier information found for this compound.
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Ifosfamide, sold under the brand name Ifex among others, is a chemotherapy medication used to treat a number of types of cancer. This includes testicular cancer, soft tissue sarcoma, osteosarcoma, bladder cancer, small cell lung cancer, cervical cancer, and ovarian cancer. It is administered by injection into a vein. Common side effects include hair loss, vomiting, blood in the urine, infections, and kidney problems. Other severe side effects include bone marrow suppression and decreased level of consciousness. Use during pregnancy will likely result in harm to the baby. Ifosfamide is in the alkylating agent and nitrogen mustard family of medications. It works by disrupting the duplication of DNA and the creation of RNA. Ifosfamide was approved for medical use in the United States in 1987. It is on the World Health Organization's List of Essential Medicines.
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Formula C7H15Cl2N2O2P
Net Charge 0
Average Mass 261.08600
Monoisotopic Mass 260.02482
InChI InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)
InChIKey HOMGKSMUEGBAAB-UHFFFAOYSA-N
SMILES ClCCNP1(=O)OCCCN1CCCl
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): 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.
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): 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.
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ChEBI Ontology
Outgoing ifosfamide (CHEBI:5864) has role alkylating agent (CHEBI:22333)
ifosfamide (CHEBI:5864) has role antineoplastic agent (CHEBI:35610)
ifosfamide (CHEBI:5864) has role environmental contaminant (CHEBI:78298)
ifosfamide (CHEBI:5864) has role immunosuppressive agent (CHEBI:35705)
ifosfamide (CHEBI:5864) has role xenobiotic (CHEBI:35703)
ifosfamide (CHEBI:5864) is a ifosfamides (CHEBI:55369)
IUPAC Name
N,3-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
INNs Sources
ifosfamida ChemIDplus
ifosfamide ChemIDplus
ifosfamidum ChemIDplus
Synonyms Sources
3-(2-chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide ChemIDplus
Iphosphamide DrugBank
Isofosfamide DrugBank
Isophosphamide KEGG COMPOUND
Isophosphamide ChemIDplus
isosfamide ChEBI
Manual Xrefs Databases
1421 DrugCentral
C07047 KEGG COMPOUND
D00343 KEGG DRUG
DB01181 DrugBank
HMDB0015312 HMDB
Ifosfamide Wikipedia
LSM-5118 LINCS
View more database links
Registry Numbers Types Sources
3778-73-2 CAS Registry Number ChemIDplus
5802893 Reaxys Registry Number Reaxys
611835 Beilstein Registry Number Beilstein
Citations
Last Modified
22 February 2017