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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:56 UTC
HMDB IDHMDB0015312
Secondary Accession Numbers
  • HMDB15312
Metabolite Identification
Common NameIfosfamide
DescriptionIfosfamide 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 intracellular molecular 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 results in cell death.
Structure
Data?1582753282
Synonyms
ValueSource
3-(2-Chloroethyl)-2-((2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxideChEBI
IfosfamidaChEBI
IfosfamidumChEBI
IphosphamideChEBI
IsofosfamideChEBI
IsophosphamideChEBI
IsosfamideChEBI
IfexKegg
Asta Z 4942HMDB
I-phosphamideHMDB
IfosfamidHMDB
Ifosfamide sterileHMDB
IfosphamideHMDB
IfsofamideHMDB
IphosphamidHMDB
Iso-endoxanHMDB
Iso endoxanHMDB
HoloxanHMDB
Chemical FormulaC7H15Cl2N2O2P
Average Molecular Weight261.086
Monoisotopic Molecular Weight260.02481966
IUPAC Name3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one
Traditional Name3-(2-chloroethyl)-2-[(2-chloroethyl)amino]-1,3,2lambda5-oxazaphosphinan-2-one
CAS Registry Number3778-73-2
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 KeyHOMGKSMUEGBAAB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazaphosphinanes
Sub ClassIsofamides
Direct ParentIsofamides
Alternative Parents
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
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point39 - 41 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility15 g/LNot Available
LogP0.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available147.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00001035
Predicted Molecular Properties
PropertyValueSource
Water Solubility15 g/LALOGPS
logP0.57ALOGPS
logP0.097ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)14.59ChemAxon
pKa (Strongest Basic)-0.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.48 m³·mol⁻¹ChemAxon
Polarizability23.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+144.3330932474
DeepCCS[M-H]-141.42530932474
DeepCCS[M-2H]-177.71130932474
DeepCCS[M+Na]+153.24830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IfosfamideClCCNP1(=O)OCCCN1CCCl2677.2Standard polar33892256
IfosfamideClCCNP1(=O)OCCCN1CCCl1826.8Standard non polar33892256
IfosfamideClCCNP1(=O)OCCCN1CCCl2035.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ifosfamide,1TMS,isomer #1C[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl2026.9Semi standard non polar33892256
Ifosfamide,1TMS,isomer #1C[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl1945.5Standard non polar33892256
Ifosfamide,1TMS,isomer #1C[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl2809.4Standard polar33892256
Ifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl2268.5Semi standard non polar33892256
Ifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl2188.5Standard non polar33892256
Ifosfamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCCN1CCCl2948.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ifosfamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gj-3950000000-d61f04c75e5216d6c4812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ifosfamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ifosfamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-qTof , Positive-QTOFsplash10-001i-0290000000-4c400c6848932e5bc3042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-qTof , Positive-QTOFsplash10-03di-1390000000-cb6bb34e3efac3f15b242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-qTof , Positive-QTOFsplash10-0udi-3910000000-2729bcf5701a78198ad52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-001i-0490000000-17ba12fd0e00df2723dc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-03di-0090000000-d4e1a660175509162e8c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-03di-0090000000-c26cb9c6b0b1cafbc7c22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-0gx3-6960000000-e4f4eadda4e355e7dd842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-0f6x-8900000000-10d5b2623785719eb1e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-0006-9500000000-d06de43b506b64b21f312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-0006-9300000000-698d7a6ed4f1837ad7212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-03di-0090000000-084cc16ffb95bd0ef9602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-03di-0090000000-1ae1b6f01a6e1a37e34c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-0gx3-6960000000-ad40c4b969e8d02866772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-0f6x-8900000000-137610f53c637d8d5b792017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-0006-9500000000-6b78178980477a0f7c082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-0006-9200000000-e6f6b95f30fc4c9fde8a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide LC-ESI-ITFT , positive-QTOFsplash10-001i-0490000000-661cabcd304902a3d4b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide , positive-QTOFsplash10-001i-0290000000-4c400c6848932e5bc3042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ifosfamide , positive-QTOFsplash10-03di-1390000000-cb6bb34e3efac3f15b242017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ifosfamide 10V, Positive-QTOFsplash10-0006-9030000000-82608eec100a23f0266e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ifosfamide 20V, Positive-QTOFsplash10-001i-9100000000-755c8d4c9c0f9d89400e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ifosfamide 40V, Positive-QTOFsplash10-0006-9000000000-8b8aed41746e222fd47a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ifosfamide 10V, Negative-QTOFsplash10-0002-1910000000-ddc3d173bfc120e5f7dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ifosfamide 20V, Negative-QTOFsplash10-0159-8900000000-e4192b3d1839133ffa5e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ifosfamide 40V, Negative-QTOFsplash10-004i-9000000000-7de8be0f841d92b197692016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01181 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01181 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01181
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3562
KEGG Compound IDC07047
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIfosfamide
METLIN IDNot Available
PubChem Compound3690
PDB IDNot Available
ChEBI ID5864
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot 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 . .