2-sulfanylethylsulfonate

2-sulfanylethylsulfonate Uses, Dosage, Side Effects, Food Interaction and all others data.

2-sulfanylethylsulfonate (commonly known by its salt form, Mesna) is a synthetic sulfhydryl (thiol) compound and is used for prophylaxis of Ifosfamide and cyclophosphamide induced hemorrhagic cystitis.

Mesna binds to and inactivates acrolein there by preventing or reducing bladder problems

2-sulfanylethylsulfonate
Uses
Dosage
Side Effect
Precautions
Interactions
Uses during Pregnancy
Uses during Breastfeeding
Accute Overdose
Food Interaction
Half Life
Volume of Distribution
Clearance
Interaction With other Medicine
Contradiction
Storage

Trade Name	2-sulfanylethylsulfonate
Generic	Coenzyme M
Coenzyme M Other Names	2-Mercaptoethane, 2-Mercaptoethanesulfonate, 2-mercaptoethylsulfonate, 2-sulfanylethylsulfonate, Coenzima M, Coenzym M, HS-CoM, reduced coenzyme M, reduced CoM
Type
Formula	C₂H₆O₃S₂
Weight	Average: 142.197 Monoisotopic: 141.975835438
Protein binding	Total plasma mesna is 28% protein bound.
Groups	Approved, Investigational
Therapeutic Class
Manufacturer
Available Country
Last Updated:	September 19, 2023 at 7:00 am

Uses

2-sulfanylethylsulfonate is a uroprotective agent used for the reduction and prophylaxis of oxazaphosphorine-induced toxicity in the urinary tract.

Mesna is a uroprotective agent and is used prophylactically to reduce ifosfamide and cyclophosphamide induced hemorrhagic cystitis.

2-sulfanylethylsulfonate is also used to associated treatment for these conditions: Hemorrhagic cystitis caused by cyclophosphamide, Hemorrhagic cystitis caused by ifosfamide

How 2-sulfanylethylsulfonate works

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.

Toxicity

The following adverse events were most common (>10%) when mesna was administered with ifosfamide: nausea, vomiting, fatigue, fever, abdominal pain, constipation, diarrhea, leukopenia, anorexia, thrombocytopenia, anemia, granulocytopenia, asthenia, headache, alopecia, and somnolence. Hypersensitivity reactions and dermatologic toxicity may occur in patients taking mesna; therefore, if either reaction occurs, mesna should be discontinued and patient should be provided with supportive care.

Food Interaction

No food interactions are expected.

Volume of Distribution

Vd = 0.652 ± 0.242 L/Kg after intravenous administration of mesna.

Elimination Route

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.