ContaminantDB: 4-Hydroxyifosfamide

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

Record Information

Version

1.0

Creation Date

2016-05-25 18:17:05 UTC

Update Date

2016-11-09 01:17:24 UTC

Accession Number

CHEM021967

Identification

Common Name

4-Hydroxyifosfamide

Class

Small Molecule

Description

4-Hydroxyifosfamide is the active metabolite of the bifunctional alkylating cytostatic drug known as ifosfamide. 4-Hydroxyifosfamide is a member of the compound class known as 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. 4-Hydroxyifosfamide is very unstable in plasma and a stabilization procedure by adding citric acid has been developed (PMID: 9172103). 4-Hydroxyifosfamide is known to pass through the blood-brain barrier, and can reach cerebrospinal fluid concentrations that are almost as high as plasma concentrations (PMID: 9677448). 4-Hydroxyifosfamide 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 PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxy-ifosfamide	HMDB
3-(2-Chloroethyl)-2-((2-chloroethyl)amino)-1,3,2-oxazaphosphinan-4-ol 2-oxide	HMDB

Chemical Formula

C₇H₁₅Cl₂N₂O₃P

Average Molecular Mass

277.085 g/mol

Monoisotopic Mass

276.020 g/mol

CAS Registry Number

67292-64-2

IUPAC Name

3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-4-hydroxy-1,3,2λ⁵-oxazaphosphinan-2-one

Traditional Name

4-hydroxyifosfamide

SMILES

OC1CCOP(=O)(NCCCl)N1CCCl

InChI Identifier

InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13)

InChI Key

JHUJMHKRHQPBRG-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
Alkanolamine
Azacycle
Oxacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organic oxygen compound
Organohalogen compound
Organic nitrogen compound
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

ifosfamides (CHEBI:80560 )

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	22.2 g/L	ALOGPS
logP	-0.06	ALOGPS
logP	-0.057	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	12.91	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.8 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.09 m³·mol⁻¹	ChemAxon
Polarizability	24.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-054o-4490000000-68b33a81b7ed61042169	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9477000000-c358b806368970e28e8a	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	splash10-0a4i-9030000000-125f3622a612b6133e45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9100000000-2dc6532567c6dd55b170	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-ba299292144772f345bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-2790000000-5f30604369be13b4f4b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-8900000000-4377372163ecc070ea4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9000000000-1212b3cc3fd363e6eef8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-6c1af332aad878673a4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0290000000-939a59c6fbceef5cc6af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00bi-3910000000-478bad8cbcb2e8e42d36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-368a494088668b022c36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2390000000-2745c533925b00075ccd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9300000000-1dd7c346907cc962b5f5	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

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

HMDB0013861

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

272429

ChEBI ID

Not Available

PubChem Compound ID

308171

Kegg Compound ID

C16553

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Kaijser GP, Ter Riet PG, de Kraker J, Bult A, Beijnen JH, Underberg WJ: Determination of 4-hydroxyifosfamide in biological matrices by high-performance liquid chromatography. J Pharm Biomed Anal. 1997 Mar;15(6):773-81. doi: 10.1016/s0731-7085(96)01893-6.

2. Kaijser GP, De Kraker J, Bult A, Underberg WJ, Beijnen JH: Pharmacokinetics of ifosfamide and some metabolites in children. Anticancer Res. 1998 May-Jun;18(3B):1941-9.

4-Hydroxyifosfamide (CHEM021967)

Structure for CHEM021967: 4-Hydroxyifosfamide