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Ifosfamide

July 24, 2017
Common Name

Ifosfamide Description

Ifosfamide is only found in individuals that have used or taken this drug. It is a positional isomer of cyclophosphamide which is active as an alkylating agent and an immunosuppressive agent. [PubChem]The exact mechanism of ifosfamide has not been determined, but appears to be similar to other alkylating agents. Ifosfamide requires biotransformation in the liver by mixed-function oxidases (cytochrome P450 system) before it becomes active. After metabolic activation, active metabolites of ifosfamide alkylate or bind with many intracellliar molecliar structures, including nucleic acids. The cytotoxic action is primarily through the alkylation of DNA, done by attaching the N-7 position of guanine to its reactive electrophilic groups. The formation of inter and intra strand cross-links in the DNA reslits in cell death. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 3-(2-Chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxideChEBI IfosfamidaChEBI IfosfamidumChEBI IphosphamideChEBI IsofosfamideChEBI IsophosphamideChEBI IsosfamideChEBI Asta Z 4942HMDB I-phosphamideHMDB IfosfamidHMDB Ifosfamide sterileHMDB IfosphamideHMDB IfsofamideHMDB IphosphamidHMDB iso-EndoxanMeSH iso EndoxanMeSH HoloxanMeSH

Chemical Formlia

C7H15Cl2N2O2P Average Molecliar Weight

261.086 Monoisotopic Molecliar Weight

260.02481966 IUPAC Name

3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinan-2-one Traditional Name

ifosfamide CAS Registry Number

3778-73-2 SMILES

ClCCNP1(=O)OCCCN1CCCl

InChI Identifier

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 Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Oxazaphosphinanes Direct Parent

Isofamides Alternative Parents

  • Phosphoric monoester diamides
  • Oxacyclic compounds
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organooxygen compounds
  • Organonitrogen compounds
  • Organochlorides
  • Organic oxides
  • Hydrocarbon derivatives
  • Alkyl chlorides

    • Substituents

  • Isofamide
  • Phosphoric monoester diamide
  • Organic phosphoric acid derivative
  • Organic phosphoric acid amide
  • Azacycle
  • Oxacycle
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organic oxygen compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Alkyl halide
  • Aliphatic heteromonocyclic compound

    • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

  • ifosfamides (CHEBI:5864 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Immunosuppressive Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point39 – 41 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.50e+01 g/LNot Available LogP0.8Not Available

    Predicted Properties

    Property Value Source Water Solubility15.0 mg/mLALOGPS logP0.57ALOGPS logP0.097ChemAxon logS-1.2ALOGPS pKa (Strongest Acidic)13.24ChemAxon pKa (Strongest Basic)0.12ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area41.57 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity58.48 m3·mol-1ChemAxon Polarizability23.94 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-001i-0490000000-17ba12fd0e00df2723dcView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-03di-0090000000-d4e1a660175509162e8cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-03di-0090000000-c26cb9c6b0b1cafbc7c2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0gx3-6960000000-e4f4eadda4e355e7dd84View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0f6x-8900000000-10d5b2623785719eb1e7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0006-9500000000-d06de43b506b64b21f31View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0006-9300000000-698d7a6ed4f1837ad721View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-03di-0090000000-084cc16ffb95bd0ef960View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-03di-0090000000-1ae1b6f01a6e1a37e34cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0gx3-6960000000-ad40c4b969e8d0286677View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0f6x-8900000000-137610f53c637d8d5b79View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0006-9500000000-6b78178980477a0f7c08View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0006-9200000000-e6f6b95f30fc4c9fde8aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-001i-0490000000-661cabcd304902a3d4b5View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-001i-0290000000-4c400c6848932e5bc304View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-03di-1390000000-cb6bb34e3efac3f15b24View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0udi-3910000000-2729bcf5701a78198ad5View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Ifosfamide Metabolism PathwaySMP00605Not Available Ifosfamide PathwaySMP00448Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01181

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01181

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-4 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01181 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    3562 KEGG Compound ID

    C07047 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Ifosfamide NuGOwiki Link

    HMDB15312 Metagene Link

    HMDB15312 METLIN ID

    Not Available PubChem Compound

    3690 PDB ID

    Not Available ChEBI ID

    5864

    Product: Quillaic acid

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
    2. Allen LM, Creaven PJ, Nelson RL: Studies on the human pharmacokinetics of isophosphamide (NSC-109724). Cancer Treat Rep. 1976 Apr;60(4):451-8. [PubMed:1277221 ]
    3. Dechant KL, Brogden RN, Pilkington T, Faulds D: Ifosfamide/mesna. A review of its antineoplastic activity, pharmacokinetic properties and therapeutic efficacy in cancer. Drugs. 1991 Sep;42(3):428-67. [PubMed:1720382 ]
    4. Schoenike SE, Dana WJ: Ifosfamide and mesna. Clin Pharm. 1990 Mar;9(3):179-91. [PubMed:2107997 ]
    5. Zalupski M, Baker LH: Ifosfamide. J Natl Cancer Inst. 1988 Jun 15;80(8):556-66. [PubMed:3286879 ]
    6. Brade WP, Herdrich K, Varini M: Ifosfamide–pharmacology, safety and therapeutic potential. Cancer Treat Rev. 1985 Mar;12(1):1-47. [PubMed:3896483 ]
    7. Wagner T: Ifosfamide clinical pharmacokinetics. Clin Pharmacokinet. 1994 Jun;26(6):439-56. [PubMed:8070218 ]
    8. Fleming RA: An overview of cyclophosphamide and ifosfamide pharmacology. Pharmacotherapy. 1997 Sep-Oct;17(5 Pt 2):146S-154S. [PubMed:9322882 ]
    9. Furlanut M, Franceschi L: Pharmacology of ifosfamide. Oncology. 2003;65 Suppl 2:2-6. [PubMed:14586139 ]
    10. Willits I, Price L, Parry A, Tilby MJ, Ford D, Cholerton S, Pearson AD, Boddy AV: Pharmacokinetics and metabolism of ifosfamide in relation to DNA damage assessed by the COMET assay in children with cancer. Br J Cancer. 2005 May 9;92(9):1626-35. [PubMed:15827549 ]
    11. (). FDA label . .

    PMID: 19408900

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