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Record Information |
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Version | 4.0 |
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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 | 2020-02-26 21:24:46 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 | |
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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 | 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 | HMDB | ASTA D 7093 | HMDB | Kendrick brand OF mesna | HMDB | Mistabron | HMDB | Mistabronco | HMDB | Sodium 2-mercaptoethanesulphonate | HMDB | UCB brand OF mesna | HMDB | Cell pharm brand OF mesna | HMDB | ASTA-D 7093 | HMDB | ASTAD 7093 | HMDB | Bristol myers squibb brand OF mesna | HMDB | MESNA-cell | HMDB | Mucofluid | HMDB | Sanfer brand OF mesna | HMDB | Ziken | HMDB | 2-Mercaptoethanesulphonate, sodium | HMDB | ASTA medica brand OF mesna | HMDB | Mesna kendrick brand | HMDB | Mesna sanfer brand | HMDB | Mesnex | HMDB | Mesnum | HMDB | Mitexan | HMDB | Bristol-myers squibb brand OF mesna | HMDB | MESNA cell | HMDB | Uromitexan | HMDB | Mesna | ChEBI |
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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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Disposition | Biological location: Source: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental 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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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-00e9-7960000000-d0e9fc5f5629ba893d57 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00e9-7960000000-d0e9fc5f5629ba893d57 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-052u-2900000000-51cd7c5f2497db0c7a15 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004m-7970000000-a5c3c33a78b251bdd12c | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-08i0-9100000000-17bded3f4e78114bc0d3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-001i-9400000000-f69174f630c88b6e6c0b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-1900000000-4ac0601c658b746cde74 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03kc-8900000000-0f9ced3911873030886c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03fr-9100000000-a5c85eeb5676f5fed8a5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001l-9600000000-b4d0e7498f823e6d5a04 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-9400000000-bc6293ab20fc276566eb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-9100000000-9f5c132d4e221797ce20 | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB09110 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023220 |
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KNApSAcK ID | C00000761 |
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Chemspider ID | 578 |
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KEGG Compound ID | C03576 |
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BioCyc ID | CoM |
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BiGG ID | Not Available |
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Wikipedia Link | Mesna |
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METLIN ID | 6978 |
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PubChem Compound | 598 |
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PDB ID | Not Available |
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ChEBI ID | 17905 |
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Food Biomarker Ontology | Not Available |
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VMH ID | COM |
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MarkerDB ID | |
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References |
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Synthesis Reference | Jary, Jiri; Dolezal, Stanislav; Grossmann, Vojtech; Benes, Milan. Method of 2-mercaptoethanesulfonic acid production. Czech. (1988), 4 pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Duran M, Aarsen G, Fokkens RH, Nibbering NM, Cats BP, de Bree PK, Wadman SK: 2-Mercaptoethanesulfonate-cysteine disulfide excretion following the administration of 2-mercaptoethanesulfonate--a pitfall in the diagnosis of sulfite oxidase deficiency. Clin Chim Acta. 1981 Mar 19;111(1):47-53. [PubMed:6784974 ]
- Khaw SL, Downie PA, Waters KD, Ashley DM, Heath JA: Adverse hypersensitivity reactions to mesna as adjunctive therapy for cyclophosphamide. Pediatr Blood Cancer. 2007 Sep;49(3):341-3. [PubMed:16333822 ]
- Links M, Lewis C: Chemoprotectants: a review of their clinical pharmacology and therapeutic efficacy. Drugs. 1999 Mar;57(3):293-308. [PubMed:10193684 ]
- Goren MP: Oral mesna: a review. Semin Oncol. 1992 Dec;19(6 Suppl 12):65-71. [PubMed:1485175 ]
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