Mesna, United States PharmacopeiaReference Standard

Base Information

• Chemical Name: Mesna, United States PharmacopeiaReference Standard
• CAS No.: 19767-45-4
• Molecular Formula: C2H5NaO3S2
• Molecular Weight: 164.182
• Hs Code.: 2930 90 98
• Mol file: 19767-45-4.mol

Synonyms:SCHEMBL179947;Ethanesulfonic acid, 2-mercapto-, sodium salt (1:1);Mesna, United States Pharmacopeia (USP) Reference Standard;Sodium 2-mercaptoethanesulfonate, BioXtra, >=98.0% (RT);Mesna, Pharmaceutical Secondary Standard;Certified Reference Material;Sodium 2-mercaptoethanesulfonate, analytical standard, >=98.0% (titration)

Chemical Property of Mesna, United States PharmacopeiaReference Standard

Chemical Property:

• Appearance/Colour: white to off-white solid
• Melting Point: >240°C dec.
• PSA: 104.38000
• LogP: 0.54220
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: Freely soluble in water, slightly soluble in ethanol (96 per cent), practically insoluble in cyclohexane
• Water Solubility.: Soluble in water. Also soluble in methanol, DMSO (33 mg/ml) and ethanol (<1 mg/ml).
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 164.96560568
• Heavy Atom Count: 8
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

Mesna ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CS(=O)(=O)O)S.[Na]
• Uses: adrenergic agonist, coronary vasodilator, Ca channel blocker Mesna reacts with acrolein and other urotoxic metabolites of oxazaphosphorines (cyclophosphamide or ifosfamide) to form stable, non-urotoxic compounds. Mesna does not have any antitumour activity, nor does it appear to interfere with the antitumour activity of antineoplastic drugs. This medication is used to protect the bladder wall from the harmful effects of some cancer-fighting drugs. 2-Mercaptoethanesulfonic acid sodium salt (Coenzyme M sodium salt, MESNA) is used as an antioxidant and cytoprotective agent in a wide variety of applications from protection from toxicity of therapeutic agents, such as cyclophosphamide to prevention from brain injury damage.
• Therapeutic Function: Mucolytic
• Clinical Use: Prophylaxis of urothelial toxicity in patients treated with ifosfamide or cyclophosphamide
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Mesna, United States PharmacopeiaReference Standard

There total 4 articles about Mesna, United States PharmacopeiaReference Standard which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

sodium 2-bromethanesulfonate (4263-52-9) → mesna (19767-45-4)

Guidance literature:

sodium 2-bromethanesulfonate; With sodium hydroxide; tiolacetic acid; In water; at 10 - 105 ℃; for 2h; Heating / reflux;

With acetic acid; In water; for 6h; Heating / reflux;

Reference yield:

dimesna → mesna (19767-45-4)

Guidance literature:

With palladium on activated charcoal; hydrogen; at 50 - 60 ℃; for 1h; under 7600.51 - 15201 Torr; Autoclave;

Reference yield:

C2H4(2)HO3S2(1-)*Na(1+) → mesna (19767-45-4)

Guidance literature:

With water-d2; In water; at 34.9 ℃; Equilibrium constant;

DOI:10.1021/ja00295a017

upstream raw materials:

sodium 2-bromethanesulfonate

Downstream raw materials:

2,2’-dithio-bis-ethane sulfonate

2-<<2-amino-1-(4-chlorophenyl)ethyl>thio>ethanesulfonic acid

Refernces

• 1、 -. "SULFANYL DERIVATIVES AND THEIR USE AS SYNTHESIS INTERMEDIATES". Page/Page column 3-4. . Retrieved 2009/04/25.
• 2、 Jarret, Ronald M.,Saunders, Martin. "A New Method for Obtaining Isotopic Fractionation Data at Multiple Sites in Rapidly Exchanging Systems". . p. 2648 - 2654. Retrieved 2007/10/02.