Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:00:14 UTC |
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Update Date | 2023-02-21 17:18:05 UTC |
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HMDB ID | HMDB0013858 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Dechloroethylifosfamide |
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Description | 3-Dechloroethylifosfamide is an inactive metabolite of the antitumour, alkylating drug Ifosfamide. It is a member of the compound class called oxazaphosphorines Oxazaphosphorines are any saturated six-membered heterocycle containing three carbon atoms and one each of oxygen, nitrogen and phosphorus, especially one in which the phosphorus atom is linked to both the nitrogen and oxygen atoms. It is formed from its side-chain oxidation leading to the liberation of chloroacetaldehyde (PMID: 9054957 ). 3-dechloroethylifosfamide can be biosynthesized from ifosfamide through the action of several CYP450 enzymes including CYP3A4, CYP3A5, and CYP2B6 (PMID: 15875221 ). The duration of ifosfamide infusion influences the amount of 3-dechloroethylifosfamide that is produced (PMID: 11408362 ). 3-dechloroethylifosfamide is only found in individuals who have consumed or received the drug Ifosfamide. |
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Structure | InChI=1S/C5H12ClN2O2P/c6-2-4-8-11(9)7-3-1-5-10-11/h1-5H2,(H2,7,8,9) |
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Synonyms | Value | Source |
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Dechloroethylcyclophosphamide | HMDB | N-(2-Chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide | HMDB | N-(2-Chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine | HMDB | (+-)-Isomer OF dechloroethylcyclophosphamide | HMDB | (R)-Isomer OF dechloroethylcyclophosphamide | HMDB | N-Dechloroethyl-cpa | HMDB | (S)-Isomer OF dechloroethylcyclophosphamide | HMDB | 3-DCE-iff | HMDB | 3-DClIF | HMDB |
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Chemical Formula | C5H12ClN2O2P |
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Average Molecular Weight | 198.588 |
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Monoisotopic Molecular Weight | 198.032491857 |
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IUPAC Name | 2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinan-2-one |
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Traditional Name | 3-dechloroethylifosfamide |
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CAS Registry Number | 36761-83-8 |
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SMILES | ClCCNP1(=O)NCCCO1 |
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InChI Identifier | InChI=1S/C5H12ClN2O2P/c6-2-4-8-11(9)7-3-1-5-10-11/h1-5H2,(H2,7,8,9) |
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InChI Key | DZKGMGPLDJOVCX-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphoric monoester diamides. These are organophosphorus compounds containing a monoamide derivative of a phosphoric acid diester functional group. They have the general structure R1OP(=O)(N(R2)R3)N(R4)R5, where R1 = organyl group and R2-R5 = H or organyl. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic phosphoric acids and derivatives |
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Sub Class | Organic phosphoramides |
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Direct Parent | Phosphoric monoester diamides |
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Alternative Parents | |
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Substituents | - Phosphoric monoester diamide
- Oxazaphosphinane
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Alkyl chloride
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Organochloride
- Organohalogen compound
- Alkyl halide
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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3-Dechloroethylifosfamide,1TMS,isomer #1 | C[Si](C)(C)N(CCCl)P1(=O)NCCCO1 | 1738.4 | Semi standard non polar | 33892256 | 3-Dechloroethylifosfamide,1TMS,isomer #1 | C[Si](C)(C)N(CCCl)P1(=O)NCCCO1 | 1606.4 | Standard non polar | 33892256 | 3-Dechloroethylifosfamide,1TMS,isomer #1 | C[Si](C)(C)N(CCCl)P1(=O)NCCCO1 | 2421.1 | Standard polar | 33892256 | 3-Dechloroethylifosfamide,1TMS,isomer #2 | C[Si](C)(C)N1CCCOP1(=O)NCCCl | 1772.4 | Semi standard non polar | 33892256 | 3-Dechloroethylifosfamide,1TMS,isomer #2 | C[Si](C)(C)N1CCCOP1(=O)NCCCl | 1557.6 | Standard non polar | 33892256 | 3-Dechloroethylifosfamide,1TMS,isomer #2 | C[Si](C)(C)N1CCCOP1(=O)NCCCl | 2442.2 | Standard polar | 33892256 | 3-Dechloroethylifosfamide,2TMS,isomer #1 | C[Si](C)(C)N(CCCl)P1(=O)OCCCN1[Si](C)(C)C | 1808.4 | Semi standard non polar | 33892256 | 3-Dechloroethylifosfamide,2TMS,isomer #1 | C[Si](C)(C)N(CCCl)P1(=O)OCCCN1[Si](C)(C)C | 1724.5 | Standard non polar | 33892256 | 3-Dechloroethylifosfamide,2TMS,isomer #1 | C[Si](C)(C)N(CCCl)P1(=O)OCCCN1[Si](C)(C)C | 2196.4 | Standard polar | 33892256 | 3-Dechloroethylifosfamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)NCCCO1 | 1987.1 | Semi standard non polar | 33892256 | 3-Dechloroethylifosfamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)NCCCO1 | 1863.2 | Standard non polar | 33892256 | 3-Dechloroethylifosfamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)NCCCO1 | 2549.7 | Standard polar | 33892256 | 3-Dechloroethylifosfamide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1CCCOP1(=O)NCCCl | 2003.9 | Semi standard non polar | 33892256 | 3-Dechloroethylifosfamide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1CCCOP1(=O)NCCCl | 1821.4 | Standard non polar | 33892256 | 3-Dechloroethylifosfamide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1CCCOP1(=O)NCCCl | 2589.3 | Standard polar | 33892256 | 3-Dechloroethylifosfamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCCN1[Si](C)(C)C(C)(C)C | 2247.8 | Semi standard non polar | 33892256 | 3-Dechloroethylifosfamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCCN1[Si](C)(C)C(C)(C)C | 2168.7 | Standard non polar | 33892256 | 3-Dechloroethylifosfamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCCl)P1(=O)OCCCN1[Si](C)(C)C(C)(C)C | 2432.3 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 3-Dechloroethylifosfamide GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-3900000000-392658bd8725e8f4d2b7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Dechloroethylifosfamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Dechloroethylifosfamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 10V, Positive-QTOF | splash10-0007-9400000000-da0eda7e219f0430b8a4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 20V, Positive-QTOF | splash10-001l-9100000000-5d5e6106a794300724af | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 40V, Positive-QTOF | splash10-0006-9000000000-fafcf55c945ad46ab368 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 10V, Negative-QTOF | splash10-000j-3900000000-c93fe9c2984f02180ddb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 20V, Negative-QTOF | splash10-0pb9-9000000000-505dc81c9537f624df62 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 40V, Negative-QTOF | splash10-004l-9000000000-e80b4317b29aefa564f2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 10V, Positive-QTOF | splash10-00di-2900000000-179e4519910dd8d006ef | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 20V, Positive-QTOF | splash10-03di-9200000000-10a1f72263ee956050fc | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 40V, Positive-QTOF | splash10-0bt9-9100000000-54b2c622d1308a287365 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 10V, Negative-QTOF | splash10-0002-0900000000-d67a78722745354ea944 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 20V, Negative-QTOF | splash10-01b9-0900000000-1d4ed7056969a6445df8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Dechloroethylifosfamide 40V, Negative-QTOF | splash10-02t9-6900000000-d3ea989132ee1a41a73c | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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General References | - Kurowski V, Wagner T: Urinary excretion of ifosfamide, 4-hydroxyifosfamide, 3- and 2-dechloroethylifosfamide, mesna, and dimesna in patients on fractionated intravenous ifosfamide and concomitant mesna therapy. Cancer Chemother Pharmacol. 1997;39(5):431-9. doi: 10.1007/s002800050594. [PubMed:9054957 ]
- Aleksa K, Matsell D, Krausz K, Gelboin H, Ito S, Koren G: Cytochrome P450 3A and 2B6 in the developing kidney: implications for ifosfamide nephrotoxicity. Pediatr Nephrol. 2005 Jul;20(7):872-85. doi: 10.1007/s00467-004-1807-3. Epub 2005 May 4. [PubMed:15875221 ]
- Kerbusch T, Mathot RA, Keizer HJ, Kaijser GP, Schellens JH, Beijnen JH: Influence of dose and infusion duration on pharmacokinetics of ifosfamide and metabolites. Drug Metab Dispos. 2001 Jul;29(7):967-75. [PubMed:11408362 ]
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