Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 04:13:50 UTC |
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Update Date | 2023-02-21 17:16:48 UTC |
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HMDB ID | HMDB0003745 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Mesna |
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Description | Mesna is a chemoprotectant. Chemoprotectants have been developed as a means of ameliorating the toxicity associated with cytotoxic agents by providing site-specific protection for normal tissues, without compromising antitumour efficacy. Mesna eliminates the risk of therapy-limiting urotoxic side effects of oxazaphosphorines. Mesna is widely used for the prevention of cyclophosphamide-related hemorrhagic cystitis. It has been associated with hypersensitivity-like cutaneous and systemic reactions in adult patients. Mesna offers significant uroprotection in patients receiving high dose cyclophosphamide, and is widely used in paediatric oncology practice It is, therefore, important to recognize that it may be associated with a rare but significant systemic adverse reaction. A hypersensitivity-like reaction to mesna was first reported in a young adult receiving treatment for Hodgkin disease over 20 years ago. Oral administration of mesna can facilitate outpatient ifosfamide therapy. Blood and urinary mesna concentrations are more steady and prolonged after oral delivery compared with after intravenous delivery. (PMID: 16333822 , 10193684 , 1485175 ). |
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Structure | InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5) |
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Synonyms | Value | Source |
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1-THIOETHANEsulfonIC ACID | ChEBI | 2-Mercaptoethanesulfonate | ChEBI | 2-Mercaptoethanesulfonic acid | ChEBI | 2-Mercaptoethanesulphonic acid | ChEBI | 2-Mercaptoethylsulfonate | ChEBI | 2-Sulfanylethylsulfonate | ChEBI | beta-Mercaptoethanesulfonic acid | ChEBI | Coenzima m | ChEBI | Coenzym m | ChEBI | CoM | ChEBI | HS-CoM | ChEBI | Mesna | ChEBI | Reduced coenzyme m | ChEBI | Reduced com | ChEBI | 1-THIOETHANEsulfonate | Generator | 1-THIOETHANEsulphonate | Generator | 1-THIOETHANEsulphonic acid | Generator | 2-Mercaptoethanesulphonate | Generator | 2-Mercaptoethylsulfonic acid | Generator | 2-Mercaptoethylsulphonate | Generator | 2-Mercaptoethylsulphonic acid | Generator | 2-Sulfanylethylsulfonic acid | Generator | 2-Sulphanylethylsulphonate | Generator | 2-Sulphanylethylsulphonic acid | Generator | b-Mercaptoethanesulfonate | Generator | b-Mercaptoethanesulfonic acid | Generator | b-Mercaptoethanesulphonate | Generator | b-Mercaptoethanesulphonic acid | Generator | beta-Mercaptoethanesulfonate | Generator | beta-Mercaptoethanesulphonate | Generator | beta-Mercaptoethanesulphonic acid | Generator | Β-mercaptoethanesulfonate | Generator | Β-mercaptoethanesulfonic acid | Generator | Β-mercaptoethanesulphonate | Generator | Β-mercaptoethanesulphonic acid | Generator | Coenzyme m | HMDB | 2 Mercaptoethanesulfonate | MeSH, HMDB | ASTA D 7093 | MeSH, HMDB | Kendrick brand OF mesna | MeSH, HMDB | Mistabron | MeSH, HMDB | Mistabronco | MeSH, HMDB | Sodium 2-mercaptoethanesulphonate | MeSH, HMDB | UCB brand OF mesna | MeSH, HMDB | Cell pharm brand OF mesna | MeSH, HMDB | ASTA-D 7093 | MeSH, HMDB | ASTAD 7093 | MeSH, HMDB | Bristol myers squibb brand OF mesna | MeSH, HMDB | MESNA-cell | MeSH, HMDB | Mucofluid | MeSH, HMDB | Sanfer brand OF mesna | MeSH, HMDB | Ziken | MeSH, HMDB | 2-Mercaptoethanesulphonate, sodium | MeSH, HMDB | ASTA medica brand OF mesna | MeSH, HMDB | Mesna kendrick brand | MeSH, HMDB | Mesna sanfer brand | MeSH, HMDB | Mesnex | MeSH, HMDB | Mesnum | MeSH, HMDB | Mitexan | MeSH, HMDB | Bristol-myers squibb brand OF mesna | MeSH, HMDB | MESNA cell | MeSH, HMDB | Uromitexan | MeSH, HMDB |
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Chemical Formula | C2H6O3S2 |
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Average Molecular Weight | 142.197 |
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Monoisotopic Molecular Weight | 141.975835438 |
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IUPAC Name | 2-sulfanylethane-1-sulfonic acid |
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Traditional Name | HS-CoM |
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CAS Registry Number | 3375-50-6 |
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SMILES | OS(=O)(=O)CCS |
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InChI Identifier | InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5) |
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InChI Key | ZNEWHQLOPFWXOF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom). |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic sulfonic acids and derivatives |
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Sub Class | Organosulfonic acids and derivatives |
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Direct Parent | Organosulfonic acids |
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Alternative Parents | |
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Substituents | - Alkanesulfonic acid
- Sulfonyl
- Organosulfonic acid
- Alkylthiol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organosulfur compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic 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 | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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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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Mesna,1TMS,isomer #1 | C[Si](C)(C)OS(=O)(=O)CCS | 1412.8 | Semi standard non polar | 33892256 | Mesna,1TMS,isomer #1 | C[Si](C)(C)OS(=O)(=O)CCS | 1259.9 | Standard non polar | 33892256 | Mesna,1TMS,isomer #1 | C[Si](C)(C)OS(=O)(=O)CCS | 1988.6 | Standard polar | 33892256 | Mesna,1TMS,isomer #2 | C[Si](C)(C)SCCS(=O)(=O)O | 1511.3 | Semi standard non polar | 33892256 | Mesna,1TMS,isomer #2 | C[Si](C)(C)SCCS(=O)(=O)O | 1374.8 | Standard non polar | 33892256 | Mesna,1TMS,isomer #2 | C[Si](C)(C)SCCS(=O)(=O)O | 2380.6 | Standard polar | 33892256 | Mesna,2TMS,isomer #1 | C[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C | 1587.9 | Semi standard non polar | 33892256 | Mesna,2TMS,isomer #1 | C[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C | 1526.2 | Standard non polar | 33892256 | Mesna,2TMS,isomer #1 | C[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C | 1902.4 | Standard polar | 33892256 | Mesna,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS | 1699.5 | Semi standard non polar | 33892256 | Mesna,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS | 1566.4 | Standard non polar | 33892256 | Mesna,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS | 2117.4 | Standard polar | 33892256 | Mesna,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)SCCS(=O)(=O)O | 1738.5 | Semi standard non polar | 33892256 | Mesna,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)SCCS(=O)(=O)O | 1637.3 | Standard non polar | 33892256 | Mesna,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)SCCS(=O)(=O)O | 2515.0 | Standard polar | 33892256 | Mesna,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C(C)(C)C | 2088.3 | Semi standard non polar | 33892256 | Mesna,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C(C)(C)C | 2032.4 | Standard non polar | 33892256 | Mesna,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)CCS[Si](C)(C)C(C)(C)C | 2076.3 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Mesna GC-MS (2 TMS) | splash10-00e9-7960000000-d0e9fc5f5629ba893d57 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Mesna GC-MS (Non-derivatized) | splash10-00e9-7960000000-d0e9fc5f5629ba893d57 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Mesna GC-EI-TOF (Non-derivatized) | splash10-052u-2900000000-51cd7c5f2497db0c7a15 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Mesna GC-EI-TOF (Non-derivatized) | splash10-004m-7970000000-a5c3c33a78b251bdd12c | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesna GC-MS (Non-derivatized) - 70eV, Positive | splash10-08i0-9100000000-17bded3f4e78114bc0d3 | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesna 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Mesna LC-ESI-QTOF , negative-QTOF | splash10-001i-9400000000-f69174f630c88b6e6c0b | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 10V, Positive-QTOF | splash10-0006-1900000000-4ac0601c658b746cde74 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 20V, Positive-QTOF | splash10-03kc-8900000000-0f9ced3911873030886c | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 40V, Positive-QTOF | splash10-03fr-9100000000-a5c85eeb5676f5fed8a5 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 10V, Negative-QTOF | splash10-001l-9600000000-b4d0e7498f823e6d5a04 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 20V, Negative-QTOF | splash10-001i-9400000000-bc6293ab20fc276566eb | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 40V, Negative-QTOF | splash10-001i-9100000000-9f5c132d4e221797ce20 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 10V, Positive-QTOF | splash10-00di-0900000000-77503e1563f802f72b03 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 20V, Positive-QTOF | splash10-03di-9400000000-e948f4e89bfaaa610a8b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 40V, Positive-QTOF | splash10-03di-9000000000-82d53190c215e025c68b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 10V, Negative-QTOF | splash10-001i-9000000000-a6fb8cd4d3dc149be309 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 20V, Negative-QTOF | splash10-001l-9700000000-765d7a0589d47fc8bb0d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesna 40V, Negative-QTOF | splash10-001i-9000000000-b4c0fc3315acedd6bf02 | 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 |
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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