Basic information
- Standard SMILES
O=S(=O)(O)CCS- InChIKey
ZNEWHQLOPFWXOF-UHFFFAOYSA-N- Molecular formula
- C2H6O3S2
- Average molar mass
- 142.2 g/mol
- Monoisotopic mass
- 141.9758364
Names & identifiers
- Preferred name
- Mercaptoethanesulfonic acid
- IUPAC
- 2-sulfanylethanesulfonic acid
- English name
- 2-Mercaptoethanesulfonic acid
- Molecular formula
- C2H6O3S2
- Molecular weight
- 142.2
Names & synonyms
Show more names
Database identifiers
- CAS
3375-50-6- PubChem CID
- 598
- DTXSID
DTXSID8023264- ChEMBL
CHEMBL1098319- ChEBI
CHEBI:17905- UNII
- VHD28S0H7F
- EC Number
- 222-167-0
- Nikkaji
- J135.783B
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 63.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 118
Experimental & physicochemical properties
Physical Description
Clear, colorless liquid.
Solid
Physicochemical properties
- Density
- 1.25 g/mL · 1.25 g/mL at 20 °C
- solubility
- DMSO
- form
- Powder
- pka
- 1 · pK1:;pK2:9.5(-1) (20°C)
- color
- Colorless to light yellow
- BRN
- 1098878 · 1098878
- InChI
- 1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)
- InChIKey
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N
- SMILES
- OS(=O)(=O)CCS
- CAS DataBase Reference
- 3375 · 3375-50-6(CAS DataBase Reference)
- FDA UNII
- 28 S0H7F · VHD28S0H7F
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 26 · NA.26
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 280 · P280-P305+P351+P338-P310
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C
- Risk Statements
- 34 · 34
- Safety Statements
- 26 · 26-27-36/37/39-45
- RIDADR
- 3265 · UN 3265 8/PG 3
- WGK Germany
- 2 · 2
- F
- 10 · 10-23
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 B · Skin Corr. 1B
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (41 of 41) of all reports.
Not Classified;Reported as not meeting GHS hazard criteria by 41 of 41 companies. For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 41 of 41 reports by companies.;There are 0 notifications provided by 0 of 41 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
Hazard information
Hazard Classes and Categories
Skin Corr. 1B (100%)
Not Classified
Toxicology
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;No information is available on the clinical use of mesna during breastfeeding. Because it is used with toxic drugs such as ifosfamide, the manufacturer recommends to not breastfeed during treatment and for 1 week after the last dose of mesna or ifosfamide.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.
Safety data
- F
- 10-23
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 2
- ridadr
- UN 3265 8/PG 3
- risk_code
- 34
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C
- safety_code
- 26-27-36/37/39-45
- Storage Class
- 8A - Combustible corrosive hazardous materials
- Hazard statements
- H314
- Hazard Classifications
- Skin Corr. 1B
- Precautionary statements
- P280-P305+P351+P338-P310
Chemistry & industry
Pharmacology
Mechanism of Action
A metabolite called acrolein is produced when ifosfamide and cyclophosphamide are metabolized. This metabolite concentrates in the bladder and causes cell death via upregulation of reactive oxygen species (ROS), and activates inducible nitric oxide synthase (iNOS) which leads to production of nitric oxide (NO). Both ROS and NO produce products which are detrimental to lipids, proteins and DNA strands. Furthermore, ROS stimulate gene expression of pro-inflammatory cytokines such as TNF-α AND IL-1β. Acrolein may also lead to ulceration of the bladder urothelium. Mesna protects against cyclophosphamide and ifosfamide induced hemorrhagic cystitis by binding to their toxic metabolites. Mesna is metabolized to dimesna and excreted by the kidneys. Glutathione dihydrogenase acts on the reabsorbed portion and produces free sulfhydryl groups. These free sulfhydryl groups bind acrolein in the bladder, allowing effective excretion and prevention of toxic effects. In addition, Mesna binds to and detoxifies a urotoxic ifosfamide metabolite called 4-hydroxy-ifosfamide.
FDA Pharmacological Classification
VHD28S0H7F
2-MERCAPTOETHANESULFONIC ACID
Established Pharmacologic Class [EPC] - Cytoprotective Agent
2-mercaptoethanesulfonic acid is a Cytoprotective Agent.
Absorption, Distribution and Excretion
Peak plasma concentrations were reached within 1.5-4 hours for free mesna, and 3-7 hours for total mesna following oral administration. The average oral bioavailability is 58% for free mesna and 89% for total mesna. Food has no effect on the urinary availability of mesna.
Within 24 hours, approximately 32% of administered dose is eliminated in the urine as mesna while 33% is eliminated as dimesna.
Vd = 0.652 ± 0.242 L/Kg after intravenous administration of mesna.
Plasma clearance of mesna = 1.23 L/h/kg
Upstream & downstream products
Upstream raw materials
Suppliers11 total
Additional notes
DefinitionChEBI: An organosulfonic acid consisting of sulfonic acid having a 2-mercaptoethyl group attached to sulfur.
Related reactions
Linked notes
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