You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for Mesna (HMDB0003745)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 04:13:50 UTC
Update Date2020-02-26 21:24:46 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
Data?1582752286
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-THIOETHANEsulfonIC ACIDChEBI
2-MercaptoethanesulfonateChEBI
2-Mercaptoethanesulfonic acidChEBI
2-Mercaptoethanesulphonic acidChEBI
2-MercaptoethylsulfonateChEBI
2-SulfanylethylsulfonateChEBI
beta-Mercaptoethanesulfonic acidChEBI
Coenzima mChEBI
Coenzym mChEBI
CoMChEBI
HS-CoMChEBI
Reduced coenzyme mChEBI
Reduced comChEBI
1-THIOETHANEsulfonateGenerator
1-THIOETHANEsulphonateGenerator
1-THIOETHANEsulphonic acidGenerator
2-MercaptoethanesulphonateGenerator
2-Mercaptoethylsulfonic acidGenerator
2-MercaptoethylsulphonateGenerator
2-Mercaptoethylsulphonic acidGenerator
2-Sulfanylethylsulfonic acidGenerator
2-SulphanylethylsulphonateGenerator
2-Sulphanylethylsulphonic acidGenerator
b-MercaptoethanesulfonateGenerator
b-Mercaptoethanesulfonic acidGenerator
b-MercaptoethanesulphonateGenerator
b-Mercaptoethanesulphonic acidGenerator
beta-MercaptoethanesulfonateGenerator
beta-MercaptoethanesulphonateGenerator
beta-Mercaptoethanesulphonic acidGenerator
Β-mercaptoethanesulfonateGenerator
Β-mercaptoethanesulfonic acidGenerator
Β-mercaptoethanesulphonateGenerator
Β-mercaptoethanesulphonic acidGenerator
Coenzyme mHMDB
2 MercaptoethanesulfonateHMDB
ASTA D 7093HMDB
Kendrick brand OF mesnaHMDB
MistabronHMDB
MistabroncoHMDB
Sodium 2-mercaptoethanesulphonateHMDB
UCB brand OF mesnaHMDB
Cell pharm brand OF mesnaHMDB
ASTA-D 7093HMDB
ASTAD 7093HMDB
Bristol myers squibb brand OF mesnaHMDB
MESNA-cellHMDB
MucofluidHMDB
Sanfer brand OF mesnaHMDB
ZikenHMDB
2-Mercaptoethanesulphonate, sodiumHMDB
ASTA medica brand OF mesnaHMDB
Mesna kendrick brandHMDB
Mesna sanfer brandHMDB
MesnexHMDB
MesnumHMDB
MitexanHMDB
Bristol-myers squibb brand OF mesnaHMDB
MESNA cellHMDB
UromitexanHMDB
MesnaChEBI
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
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.7 g/LALOGPS
logP-1.5ALOGPS
logP-0.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)-1.2ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.13 m³·mol⁻¹ChemAxon
Polarizability12.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00e9-7960000000-d0e9fc5f5629ba893d57Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00e9-7960000000-d0e9fc5f5629ba893d57Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052u-2900000000-51cd7c5f2497db0c7a15Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004m-7970000000-a5c3c33a78b251bdd12cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i0-9100000000-17bded3f4e78114bc0d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-9400000000-f69174f630c88b6e6c0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-4ac0601c658b746cde74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kc-8900000000-0f9ced3911873030886cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-9100000000-a5c85eeb5676f5fed8a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-9600000000-b4d0e7498f823e6d5a04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9400000000-bc6293ab20fc276566ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9100000000-9f5c132d4e221797ce20Spectrum
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 LinkMesna
METLIN ID6978
PubChem Compound598
PDB IDNot Available
ChEBI ID17905
Food Biomarker OntologyNot Available
VMH IDCOM
MarkerDB ID
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)Download (PDF)
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 ]