基本情報
- 標準SMILES
O=S(=O)(O)CCS- InChIKey
ZNEWHQLOPFWXOF-UHFFFAOYSA-N- 分子式
- C2H6O3S2
- 平均分子量
- 142.2 g/mol
- 単同位体質量
- 141.9758364
名称と識別子
- 優先名称
- Mercaptoethanesulfonic acid
- IUPAC
- 2-sulfanylethanesulfonic acid
- 現地名
- 2-メルカプト-1-エタンスルホン酸
- 英語名
- 2-Mercaptoethanesulfonic acid
- 分子式
- C2H6O3S2
- 分子量
- 142.2
名称と別名
名称をさらに表示
データベース識別子
- CAS
3375-50-6- PubChem CID
- 598
- DTXSID
DTXSID8023264- ChEMBL
CHEMBL1098319- ChEBI
CHEBI:17905- UNII
- VHD28S0H7F
- EC Number
- 222-167-0
- Nikkaji
- J135.783B
物性
構造計算による物性
- XLogP
- -0.6
- 極性表面積
- 63.8 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 2
- 重原子数
- 7
- 形式電荷
- 0
- 複雑度
- 118
実験および物理化学的性質
Physical Description
Clear, colorless liquid.
Solid
物理化学的性質
- 比重(密度)
- 1.25 g/mL · 1.25 g/mL at 20 °C
- 溶解性
- DMSO
- 外見
- Powder
- 酸解離定数(Pka)
- 1 · pK1:;pK2:9.5(-1) (20°C)
- 色
- 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 データベース
- 3375 · 3375-50-6(CAS DataBase Reference)
安全と法規制
GHS分類
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]
危険有害性情報
Hazard Classes and Categories
Skin Corr. 1B (100%)
Not Classified
毒性情報
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.
安全データ
- 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
- Hazard Classifications
- Skin Corr. 1B
- ストレージクラス
- 8A - Combustible corrosive hazardous materials
化学と産業
薬理情報
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
上流・下流製品情報
上流原料
サプライヤー11 社
補足説明
定義ChEBI: An organosulfonic acid consisting of sulfonic acid having a 2-mercaptoethyl group attached to sulfur.
関連反応
関連ノート
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