I4909

Sigma-Aldrich

Ifosfamide

≥98%

Synonym(s):
N,3-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine-2-oxide, Ifex
Empirical Formula (Hill Notation):
C7H15Cl2N2O2P
CAS Number:
Molecular Weight:
261.09
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥98%

shipped in

wet ice

storage temp.

2-8°C

SMILES string

ClCCNP1(=O)OCCCN1CCCl

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

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Packaging

1, 5 g in glass bottle

Biochem/physiol Actions

Ifosfamide is a nitrogen mustard compound that is a structural isomer of cyclophosphamide. Ifosfamide is a prodrug that must be transformed by cytochrome P450 to the biologically active component. It is used as an antineoplastic agent in cancer chemotherapy, but ifosfamide is more likely to cause renal toxicity than cyclophosphamide.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. I4909.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

hazcat

Acute Tox. 3 Oral - Carc. 1B - Eye Irrit. 2 - Muta. 1B - Repr. 1B

storage_class_code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Takako Eto et al.
Gynecologic oncology, 131(3), 574-580 (2013-09-11)
We previously reported on the role of cytoreduction in 248 patients with surgical stage IVb endometrial cancer (EMCA). This study aimed to evaluate the clinical characteristics, prognosis according to initial treatment, and impact of preoperative chemotherapy in the overall population...
S Stacchiotti et al.
European journal of cancer (Oxford, England : 1990), 49(10), 2376-2383 (2013-04-10)
To report on anthracycline-based chemotherapy in a retrospective case-series analysis of solitary fibrous tumour (SFT) patients treated within the Italian Rare Cancer Network. We reviewed a set of SFT treated with chemotherapy since 2002, focusing on anthracycline, administered alone or...
Andrea B Apolo et al.
Journal of the National Cancer Institute, 105(7), 499-503 (2013-02-16)
A prognostic model that predicts overall survival (OS) for metastatic urothelial cancer (MetUC) patients treated with cisplatin-based chemotherapy was developed, validated, and compared with a commonly used Memorial Sloan-Kettering Cancer Center (MSKCC) risk-score model. Data from 7 protocols that enrolled...
M Tiseo et al.
British journal of cancer, 108(8), 1695-1703 (2013-04-04)
The FAST was a factorial trial in first-line treatment of advanced non-small-cell lung cancer (NSCLC), addressing the role of replacing cisplatin with a non-platinum agent. The prognostic and predictive effect of ERCC1/BRCA1 expression and ERCC1/XPD/XRCC1-3 gene polymorphisms on outcomes of...
Evaristus C Mbanefo et al.
Scientific reports, 9(1), 1586-1586 (2019-02-09)
Ifosfamide and other oxazaphosphorines can result in hemorrhagic cystitis, a constellation of complications caused by acrolein metabolites. We previously showed that a single dose of IPSE (Interleukin-4-inducing principle from Schistosoma eggs), a schistosome-derived host modulatory protein, can ameliorate ifosfamide-related cystitis;...

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