PharmGKB: The Pharmacogenomics Knowledge Base

Drug/Small Molecule:
ifosfamide

2D structure

Overview

Generic Names: Asta Z 4942; I-Phosphamide; Ifosfamid; Ifosfamide Sterile; Ifsofamide; Iphosphamid; Iphosphamide; Isofosfamide; Isophosphamide
Trade Names: Cyfos; Holoxan 1000; IFEX; Ifex/Mesnex Kit; Ifosfamide/Mesna Kit; Isoendoxan; Mitoxana; Naxamide
PharmGKB Accession Id: PA449964

Description

Positional isomer of cyclophosphamide which is active as an alkylating agent and an immunosuppressive agent. PubChem (source: Drug Bank)

Indication

For third line chemotherapy of germ cell testicular cancer. It should ordinarily be used in combination with a prophylactic agent for hemorrhagic cystitis, such as mesna. (source: Drug Bank)

ATC Therapeutic Category

  • L01AA:Nitrogen mustard analogues

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

After metabolic activation, active metabolites of ifosfamide alkylate or bind with many intracellular molecular structures, including nucleic acids. The cytotoxic action is primarily due to cross-linking of strands of DNA and RNA, as well as inhibition of protein synthesis. (source: Drug Bank)

Pharmacology

Ifosfamide selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of ifosfamide-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Primarily hepatic (source: Drug Bank)

Protein Binding

Minimal (source: Drug Bank)

Toxicity

LD<sub>50</sub> (mouse) = 390-1005 mg/kg, LD<sub>50</sub> (rat) = 150-190 mg/kg. Side effects include nausea, vomiting and myelosuppression. Toxic effects include central nervous system toxicity (confusion, hallucinations) and urotoxic effects (cystitis, blood in urine). (source: Drug Bank)

Isomeric SMILES Code:

C1CN(P(=O)(OC1)NCCCl)CCCl (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
No phenotype data Genotype Data Available Literature annotations available Has annotations
CYP2A6
  •   
  •   
  • PK
  •   
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2B6
  •   
  • PD
  • PK
  • FA
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
NR1I2
  •   
  •   
  •   
  • FA
  •   
Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
DNMT1 Uncurated Annotation (source: Drug Bank)

A list of non-curated publications that mention this drug along with other drugs is available.

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
Neoplasms
  •   
  •   
  • PK
  •   
  • GN
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB01181
KEGG Drug ID:
D00343
PubChem Compound ID:
3690
PubChem Substance ID:
162510

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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