ContaminantDB: 3-Dechloroethylifosfamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:17:02 UTC

Update Date

2016-11-09 01:17:24 UTC

Accession Number

CHEM021965

Identification

Common Name

3-Dechloroethylifosfamide

Class

Small Molecule

Description

3-Dechloroethylifosfamide is an inactive metabolite of the antitumour, alkylating drug Ifosfamide. It is a member of the compound class called oxazaphosphorines Oxazaphosphorines are any saturated six-membered heterocycle containing three carbon atoms and one each of oxygen, nitrogen and phosphorus, especially one in which the phosphorus atom is linked to both the nitrogen and oxygen atoms. It is formed from its side-chain oxidation leading to the liberation of chloroacetaldehyde (PMID: 9054957). 3-dechloroethylifosfamide can be biosynthesized from ifosfamide through the action of several CYP450 enzymes including CYP3A4, CYP3A5, and CYP2B6 (PMID: 15875221). The duration of ifosfamide infusion influences the amount of 3-dechloroethylifosfamide that is produced (PMID: 11408362). 3-dechloroethylifosfamide is only found in individuals who have consumed or received the drug Ifosfamide.

Contaminant Sources

HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Dechloroethylcyclophosphamide	HMDB
N-(2-Chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide	HMDB
N-(2-Chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine	HMDB
(+-)-Isomer OF dechloroethylcyclophosphamide	HMDB
(R)-Isomer OF dechloroethylcyclophosphamide	HMDB
N-Dechloroethyl-cpa	HMDB
(S)-Isomer OF dechloroethylcyclophosphamide	HMDB
3-DCE-iff	HMDB
3-DClIF	HMDB

Chemical Formula

C₅H₁₂ClN₂O₂P

Average Molecular Mass

198.588 g/mol

Monoisotopic Mass

198.032 g/mol

CAS Registry Number

36761-83-8

IUPAC Name

2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinan-2-one

Traditional Name

3-dechloroethylifosfamide

SMILES

ClCCNP1(=O)NCCCO1

InChI Identifier

InChI=1S/C5H12ClN2O2P/c6-2-4-8-11(9)7-3-1-5-10-11/h1-5H2,(H2,7,8,9)

InChI Key

DZKGMGPLDJOVCX-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphoric monoester diamides. These are organophosphorus compounds containing a monoamide derivative of a phosphoric acid diester functional group. They have the general structure R1OP(=O)(N(R2)R3)N(R4)R5, where R1 = organyl group and R2-R5 = H or organyl.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Organic phosphoramides

Direct Parent

Phosphoric monoester diamides

Alternative Parents

Substituents

Phosphoric monoester diamide
Oxazaphosphinane
Organoheterocyclic compound
Azacycle
Oxacycle
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alkyl halide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

phosphorodiamide (CHEBI:80558 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	20.3 g/L	ALOGPS
logP	-0.54	ALOGPS
logP	-0.79	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	12.73	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.24 m³·mol⁻¹	ChemAxon
Polarizability	17.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3900000000-392658bd8725e8f4d2b7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-9400000000-da0eda7e219f0430b8a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-9100000000-5d5e6106a794300724af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-fafcf55c945ad46ab368	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-3900000000-c93fe9c2984f02180ddb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-9000000000-505dc81c9537f624df62	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9000000000-e80b4317b29aefa564f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-2900000000-179e4519910dd8d006ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9200000000-10a1f72263ee956050fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bt9-9100000000-54b2c622d1308a287365	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-d67a78722745354ea944	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-0900000000-1d4ed7056969a6445df8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02t9-6900000000-d3ea989132ee1a41a73c	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0013858

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Kurowski V, Wagner T: Urinary excretion of ifosfamide, 4-hydroxyifosfamide, 3- and 2-dechloroethylifosfamide, mesna, and dimesna in patients on fractionated intravenous ifosfamide and concomitant mesna therapy. Cancer Chemother Pharmacol. 1997;39(5):431-9. doi: 10.1007/s002800050594.

2. Aleksa K, Matsell D, Krausz K, Gelboin H, Ito S, Koren G: Cytochrome P450 3A and 2B6 in the developing kidney: implications for ifosfamide nephrotoxicity. Pediatr Nephrol. 2005 Jul;20(7):872-85. doi: 10.1007/s00467-004-1807-3. Epub 2005 May 4.

3. Kerbusch T, Mathot RA, Keizer HJ, Kaijser GP, Schellens JH, Beijnen JH: Influence of dose and infusion duration on pharmacokinetics of ifosfamide and metabolites. Drug Metab Dispos. 2001 Jul;29(7):967-75.

3-Dechloroethylifosfamide (CHEM021965)

Structure for CHEM021965: 3-Dechloroethylifosfamide