2-Mercaptoethansulfonsure
Mercaptoethanesulfonic acid
Grundinformationen
- CAS
3375-50-6- Standard-SMILES
O=S(=O)(O)CCS- InChIKey
ZNEWHQLOPFWXOF-UHFFFAOYSA-N- Summenformel
- C2H6O3S2
- Durchschnittliche Molmasse
- 142,2 g/mol
- Monoisotopische Masse
- 141,9758364
Überblick
Coenzyme M is an organosulfonic acid consisting of sulfonic acid having a 2-mercaptoethyl group attached to sulfur. It has a role as a coenzyme. It is a thiol and an organosulfonic acid. It is a conjugate acid of a coenzyme M(1-).
Namen und Bezeichner
- Bevorzugter Name
- Mercaptoethanesulfonic acid
- IUPAC
- 2-sulfanylethanesulfonic acid
- Lokaler Name
- 2-Mercaptoethansulfonsure
- Englischer Name
- 2-Mercaptoethanesulfonic acid
- Summenformel
- C2H6O3S2
- Molmasse
- 142.2
Namen und Synonyme
2-Mercaptoethanesulfonic acid3375-50-6coenzyme Mreduced coenzyme MMercaptoethanesulfonic acidHS-CoMreduced CoMbeta-Mercaptoethanesulfonic acid2-mercaptoethylsulfonate2-sulfanylethylsulfonate1-THIOETHANESULFONIC ACIDVHD28S0H7F
Weitere Namen anzeigen
ComC035762-MercaptoethanesulfonateMesna2-Mercaptoethanesulfonate
DTXSID8023264CHEBI:17905RefChem:925502DTXCID103264222-167-02-sulfanylethane-1-sulfonate2-sulfanylethanesulfonic acid2-Mercaptoethanesulphonic acid
Datenbank-Bezeichner
- CAS
3375-50-6- PubChem CID
- 598
- DTXSID
DTXSID8023264- ChEMBL
CHEMBL1098319- ChEBI
CHEBI:17905- UNII
- VHD28S0H7F
- EC Number
- 222-167-0
- Nikkaji
- J135.783B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,6
- Polarare Oberfläche (TPSA)
- 63,8 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 118
Experimentelle und physikochemische Eigenschaften
Chemical ClassesOther Classes -> Sulfur Compounds
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
Human DrugsBreast Feeding; Lactation; Milk, Human; Protective Agents
Physical Description
Clear, colorless liquid.
Solid
Physikochemische Eigenschaften
- Dichte
- 1.25 g/mL · 1.25 g/mL at 20 °C
- Löslichkeit
- DMSO
- Aggregatzustand
- Powder
- pka
- 1 · pK1:;pK2:9.5(－1) (20°C)
- Farbe
- 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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
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 CategoriesSkin Corr. 1B (100%)
Toxikologische Informationen
Adverse EffectsDermatotoxin - Skin burns.
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- F
- 10-23
- wgk
- 2
- ridadr
- UN 3265 8/PG 3
- risk_code
- 34
- hazard_code
- C
- safety_code
- 26-27-36/37/39-45
- Speicherklasse
- 8A - Combustible corrosive hazardous materials
Chemie und Industrie
Pharmakologische Informationen
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
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.
FDA Pharmacological Classification
VHD28S0H7F
2-MERCAPTOETHANESULFONIC ACID
Established Pharmacologic Class [EPC] - Cytoprotective Agent
2-mercaptoethanesulfonic acid is a Cytoprotective Agent.
MeSH Pharmacological ClassificationSynthetic or natural substances which are given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.
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