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I0060000

Ifosfamide

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Ifex, N,3-Bis(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine-2-oxide

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About This Item

Empirical Formula (Hill Notation):
C7H15Cl2N2O2P
CAS Number:
3778-73-2
Molecular Weight:
261.09
MDL number:
MFCD00057374
UNSPSC Code:
41116107
PubChem Substance ID:
329815295
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

ifosfamide

manufacturer/tradename

EDQM

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

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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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Ifosfamide EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

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.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Metin Tascilar et al.
The oncologist, 12(11), 1351-1360 (2007-12-07)
The treatment outcome of patients with locally advanced and metastatic soft tissue sarcomas is poor. Doxorubicin is regarded as standard treatment, but its use is featured by the occurrence of cardiotoxicity. This hinders the administration of this drug at high
Priti N Patel
The Annals of pharmacotherapy, 40(2), 299-303 (2006-01-05)
To evaluate the use of methylene blue for the treatment of ifosfamide-induced encephalopathy. MEDLINE (1966-August 2005) and International Pharmaceutical Abstracts (1971-August 2005) were searched using the terms methylene blue, ifosfamide, encephalopathy, and neurotoxicity. Several case reports and one retrospective chart
Jean-Yves Blay et al.
European journal of cancer (Oxford, England : 1990), 50(6), 1137-1147 (2014-02-12)
This randomised phase III trial evaluated first-line trabectedin versus doxorubicin-based chemotherapy (DXCT) in patients with advanced/metastatic translocation-related sarcomas (TRS). Patients were randomly assigned (1:1) to receive trabectedin 1.5mg/m2 24-h intravenous (i.v.) infusion every 3 weeks (q3wk) (Arm A), or doxorubicin
T Ajithkumar et al.
Clinical oncology (Royal College of Radiologists (Great Britain)), 19(2), 108-114 (2007-03-16)
Encephalopathy is a potentially fatal toxicity of ifosfamide. Clinical manifestations of encephalopathy range from fatigue and confusion to coma and death. Early identification of this toxicity and prompt cessation of ifosfamide are the essential elements in the management of ifosfamide
Renée L Mulder et al.
The Cochrane database of systematic reviews, (2)(2), CD006300-CD006300 (2010-02-19)
Alkylating agents, such as cyclophosphamide and ifosfamide, play a major role in the improved survival of children and young adults with bone and soft tissue sarcoma. However, there is still controversy as to their comparative anti-tumour efficacy and possible adverse
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