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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 04:13:50 UTC

Update Date

2023-02-21 17:16:48 UTC

HMDB ID

HMDB0003745

Secondary Accession Numbers

HMDB03745

Metabolite Identification

Common Name

Mesna

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 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
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

Chemical Formula

C₂H₆O₃S₂

Average Molecular Weight

142.197

Monoisotopic Molecular Weight

141.975835438

IUPAC Name

2-sulfanylethane-1-sulfonic acid

Traditional Name

HS-CoM

CAS Registry Number

3375-50-6

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 Key

ZNEWHQLOPFWXOF-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfonic acids and derivatives

Sub Class

Organosulfonic acids and derivatives

Direct Parent

Organosulfonic acids

Alternative Parents

Substituents

Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Alkylthiol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

thiol (CHEBI:17905 )
organosulfonic acid (CHEBI:17905 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0003745)

Source

Endogenous

Endogenous (HMDB: HMDB0003745)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003745)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.7 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-0.4	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	-1.2	ChemAxon
pKa (Strongest Basic)	-9.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	29.13 m³·mol⁻¹	ChemAxon
Polarizability	12.54 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	126.924	31661259
DarkChem	[M-H]-	119.074	31661259
DeepCCS	[M+H]+	128.0	30932474
DeepCCS	[M-H]-	125.966	30932474
DeepCCS	[M-2H]-	161.561	30932474
DeepCCS	[M+Na]+	135.972	30932474
AllCCS	[M+H]+	131.8	32859911
AllCCS	[M+H-H2O]+	127.7	32859911
AllCCS	[M+NH4]+	135.5	32859911
AllCCS	[M+Na]+	136.6	32859911
AllCCS	[M-H]-	132.9	32859911
AllCCS	[M+Na-2H]-	136.8	32859911
AllCCS	[M+HCOO]-	141.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mesna	OS(=O)(=O)CCS	2289.3	Standard polar	33892256
Mesna	OS(=O)(=O)CCS	1003.0	Standard non polar	33892256
Mesna	OS(=O)(=O)CCS	1355.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
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

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
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 Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
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 Spectra

Spectrum Type	Description	Deposition Date	Source	View
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 Spectra

Spectrum Type	Description	Deposition Date	Source	View
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

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09110

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Coenzyme M

METLIN ID

Not Available

PubChem Compound

598

PDB ID

Not Available

ChEBI ID

17905

Food Biomarker Ontology

Not Available

VMH ID

COM

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Jary, 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

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 ]

Showing metabocard for Mesna (HMDB0003745)

MOL for HMDB0003745 (Mesna)

3D MOL for HMDB0003745 (Mesna)

3D SDF for HMDB0003745 (Mesna)

3D-SDF for HMDB0003745 (Mesna)

PDB for HMDB0003745 (Mesna)

3D PDB for HMDB0003745 (Mesna)

SMILES for HMDB0003745 (Mesna)

INCHI for HMDB0003745 (Mesna)

Structure for HMDB0003745 (Mesna)

3D Structure for HMDB0003745 (Mesna)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra