Mercaptoethanesulfonic acid

HCID 598CAS 3375-50-6

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

2-Mercaptoethanesulfonic acid3375-50-6coenzyme Mreduced coenzyme MMercaptoethanesulfonic acidHS-CoMreduced CoMbeta-Mercaptoethanesulfonic acid2-mercaptoethylsulfonate2-sulfanylethylsulfonate1-THIOETHANESULFONIC ACIDVHD28S0H7F
Show more names
ComC035762-MercaptoethanesulfonateMesna2-Mercaptoethanesulfonate
DTXSID8023264CHEBI:17905RefChem:925502DTXCID103264222-167-02-sulfanylethane-1-sulfonate2-sulfanylethanesulfonic acid2-Mercaptoethanesulphonic acid

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

Experimental & physicochemical properties

Physical Description · 2 items

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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

Hazards SummaryIntravenous LD50 (rat) = 1,800 mg/kg; [RTECS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Pierce Biotechnology MSDS] See Methanesulfonic acid.
Hazard Classes and Categories · 2 items

Skin Corr. 1B (100%)

Not Classified

Toxicology

Adverse EffectsDermatotoxin - Skin burns.;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.
Effects During Pregnancy and Lactation · 1 item

◉ 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

Chemistry & industry

Pharmacology

ATC CodeV03AF01
Protein BindingTotal plasma mesna is 28% protein bound.
PharmacodynamicsMesna binds to and inactivates acrolein there by preventing or reducing bladder problems
Mechanism of Action · 1 item

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.

Biological Half-LifeThe elimination half-life is 0.36 hours for mesna and 1.17 hours for dimesna.
Metabolism/MetabolitesMesna undergoes rapid oxidation to mesna disulfide (dimesna) which is its major metabolite.

Upstream & downstream products

Upstream raw materials

Suppliers11 total

Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
Syntechem Co.,Ltd[email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
泰州市众致生物科技有限公司[email protected] 15066129350 · [email protected]

Additional notes

DefinitionChEBI: An organosulfonic acid consisting of sulfonic acid having a 2-mercaptoethyl group attached to sulfur.

Related reactions

5 records

Linked notes

Loading…