Ifosfamide

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Structural formula
Structure of ifosfamide
General
Non-proprietary name Ifosfamide
other names
  • ( RS ) -3- (2-chloroethyl) -2 - [(2-chloroethyl) amino] -2 H -1,3,2-oxazaphosphinane-2-oxide ( IUPAC )
  • Ifosfamidum ( Latin )
Molecular formula C 7 H 15 Cl 2 N 2 O 2 P
Brief description

white to almost white, fine, crystalline, hygroscopic powder

External identifiers / databases
CAS number 3778-73-2
EC number 223-237-3
ECHA InfoCard 100.021.126
PubChem 3690
DrugBank DB01181
Wikidata Q418560
Drug information
ATC code

L01 AA06

Drug class

Cytostatic , nitrogen mustard

Mechanism of action

Alkylation

properties
Molar mass 261.09 g · mol -1
Physical state

firmly

Melting point

39-41 ° C

solubility
  • little in water (3.78 g l −1 at 25 ° C)
  • easily soluble in dichloromethane
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301-319
P: 301 + 310-305 + 351 + 338
Toxicological data

143 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ifosfamide (trade name Holoxan ® ) belongs to the group of nitrogen mustard compounds having alkylating action . The substance is mostly used in combination with other cytostatics for the treatment of cancer diseases in the context of chemotherapy. Ifosfamide is a positional isomer of cyclophosphamide and belongs to the group of oxazaphosphorines.

effectiveness

Cancers

Ifosfamide is used as a cytostatic agent in a number of malignant diseases (cancers). It is mostly used in combination with other cytostatics.

Adults

Children and young people

Side effects

It often leads to a reduced white blood cell count (dose-limiting bone marrow depression ), nausea, and hair loss. The risk of developing secondary neoplasms, especially leukemia and bladder tumors, is increased, especially with high cumulative doses. Encephalopathy , which occurs in up to 50% of patients, is also typical with ifosfamide administration . In addition, ifosfamide chemotherapy can lead to hemorrhagic cystitis . On the other hand, an antidote is administered parallel to the administration of ifosfamide: MESNA (mercapto-ethanesulfonate sodium).

Vaccinations with dead vaccines are not effective under ifosfamide treatment because of its immunosuppressive and cytostatic effects.

Contraindications (contraindications)

  • Pregnancy . Pregnancy should be excluded before ifosfamide therapy; an existing pregnancy is a contraindication to the use of ifosfamide. Adequate contraception should be used during therapy to prevent pregnancy.
  • Vaccinations with live vaccines . Because of their cytostatic and immunosuppressive effects, vaccinations with live vaccines are potentially dangerous during treatment with ifosfamide and should therefore be avoided.

Web links

Individual evidence

  1. ↑ a b European Pharmacopoeia Commission (Ed.): EUROPEAN PHARMACOPOE 6TH EDITION . tape 6.0-6.3 , 2008.
  2. ↑ Mary Adele J. O'Neil: The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals . Ed .: Merck & Co., Inc. 14th Edition. Elsevier, Whitehouse Station, NJ, USA 2006, ISBN 978-0-911910-00-1 .
  3. ↑ a b Entry on Ifosfamide in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ a b sheet ifosfamide at Sigma-Aldrich , accessed on 4 April 2011 ( PDF ).