ChemFOnt: Showing chemical card for Ifosfamide (CFc000009592)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:46 UTC

Chemfont ID

CFc000009592

Molecule Identification

Common Name

Ifosfamide

Definition

Ifosfamide is only found in individuals that have used or taken this drug. It is a positional isomer of cyclophosphamide which is active as an alkylating agent and an immunosuppressive agent. [PubChem]The exact mechanism of ifosfamide has not been determined, but appears to be similar to other alkylating agents. Ifosfamide requires biotransformation in the liver by mixed-function oxidases (cytochrome P450 system) before it becomes active. After metabolic activation, active metabolites of ifosfamide alkylate or bind with many intracellular molecular structures, including nucleic acids. The cytotoxic action is primarily through the alkylation of DNA, done by attaching the N-7 position of guanine to its reactive electrophilic groups. The formation of inter and intra strand cross-links in the DNA results in cell death.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(2-Chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide	ChEBI
Ifosfamida	ChEBI
Ifosfamidum	ChEBI
Iphosphamide	ChEBI
Isofosfamide	ChEBI
Isophosphamide	ChEBI
Isosfamide	ChEBI
Ifex	Kegg
Asta Z 4942	HMDB
I-phosphamide	HMDB
Ifosfamid	HMDB
Ifosfamide sterile	HMDB
Ifosphamide	HMDB
Ifsofamide	HMDB
Iphosphamid	HMDB
Iso-endoxan	HMDB
Iso endoxan	HMDB
Holoxan	HMDB

Chemical Formula

C₇H₁₅Cl₂N₂O₂P

Average Molecular Weight

261.086

Monoisotopic Molecular Weight

260.02481966

IUPAC Name

3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one

Traditional Name

3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one

CAS Registry Number

3778-73-2

SMILES

ClCCNP1(=O)OCCCN1CCCl

InChI Identifier

InChI=1S/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12)

InChI Key

HOMGKSMUEGBAAB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isofamides. These are oxazaphospholanes containing the isofamide skeleton. Isofamide is a heterocyclic compound made up of a 1,3,2-oxazaphospholane, where the phosphorus atom is part of a phosphodiamide group, and the oxazaphospholane is substituted by two haloalkyl chains.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazaphosphinanes

Sub Class

Isofamides

Direct Parent

Isofamides

Alternative Parents

Substituents

Isofamide
Phosphoric monoester diamide
Organic phosphoric acid derivative
Organic phosphoric acid amide
Azacycle
Oxacycle
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organic oxygen compound
Organohalogen compound
Organic nitrogen compound
Alkyl halide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ifosfamides (CHEBI:5864 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015312)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ifosfamide Action Pathway (PathBank: SMP0000448)

Metabolic pathway

Ifosfamide Metabolism Pathway (PathBank: SMP0000605)

Role

Industrial application

Antineoplastic agent (HMDB: HMDB0015312)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Immunosuppressive Agent (HMDB: HMDB0015312)

Biological role

Alkylating agent (HMDB: HMDB0015312)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	15 g/L	ALOGPS
logP	0.57	ALOGPS
logP	0.097	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	14.59	ChemAxon
pKa (Strongest Basic)	-0.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.48 m³·mol⁻¹	ChemAxon
Polarizability	23.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon