Mesna

IUPAC: sodium 2- sulfanylethansulfonat

  • V03AF01
  • R05CB05
  • Mucolytic
  • Antidote

Soluble in water

Attention

4440 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Mesna (2- mercaptoethanesulfonate sodium, trade name: Uromitexan, Manufacturer: Baxter International ) is a drug which is a so-called Zytoprotektor in chemotherapy for neutralization of toxic metabolic products (metabolites ), which are formed during treatment with oxazaphosphorins. The oxazaphosphorins include cyclophosphamide, ifosfamide, and trofosfamide.

With its sulfhydryl mesna binds and neutralizes the toxic metabolite acrolein, which can cause a hemorrhagic cystitis with hematuria and is responsible for other side effects. Acrolein formed by biotransformation in the liver of the oxazaphosphorines.

Furthermore, patients receive a lot of fluid that helps the harmful metabolites can be excreted through the kidneys quicker. Another Sulfhydrylgruppendonator example, N-acetyl cysteine ​​, which is often used in combination with mesna.

Another application had mesna as a mucolytic agent, in this indication it was marketed under the name Mistabronco. With the authorization to lapse on 30 June 2008, this drug has been withdrawn from the market.

Synthesis

Mesna is produced in a two-step synthesis of thiourea and 2- bromoethane:

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