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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 04:13:50 UTC
Update Date2023-02-21 17:16:48 UTC
HMDB IDHMDB0003745
Secondary Accession Numbers
  • HMDB03745
Metabolite Identification
Common NameMesna
DescriptionMesna 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 ).
Structure
Thumb
Synonyms
Chemical FormulaC2H6O3S2
Average Molecular Weight142.197
Monoisotopic Molecular Weight141.975835438
IUPAC Name2-sulfanylethane-1-sulfonic acid
Traditional NameHS-CoM
CAS Registry Number3375-50-6
SMILES
OS(=O)(=O)CCS
InChI Identifier
InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)
InChI KeyZNEWHQLOPFWXOF-UHFFFAOYSA-N
Chemical Taxonomy
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Alkanesulfonic acid
  • Sulfonyl
  • Organosulfonic acid
  • Alkylthiol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09110
Phenol Explorer Compound IDNot Available
FooDB IDFDB023220
KNApSAcK IDC00000761
Chemspider ID578
KEGG Compound IDC03576
BioCyc IDCoM
BiGG IDNot Available
Wikipedia LinkCoenzyme M
METLIN IDNot Available
PubChem Compound598
PDB IDNot Available
ChEBI ID17905
Food Biomarker OntologyNot Available
VMH IDCOM
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceJary, Jiri; Dolezal, Stanislav; Grossmann, Vojtech; Benes, Milan. Method of 2-mercaptoethanesulfonic acid production. Czech. (1988), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. Links M, Lewis C: Chemoprotectants: a review of their clinical pharmacology and therapeutic efficacy. Drugs. 1999 Mar;57(3):293-308. [PubMed:10193684 ]
  4. Goren MP: Oral mesna: a review. Semin Oncol. 1992 Dec;19(6 Suppl 12):65-71. [PubMed:1485175 ]