2-Mercaptoethane

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

2-Mercaptoethane (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

Trade Name 2-Mercaptoethane
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
2-Mercaptoethane
2-Mercaptoethane

Uses

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

How 2-Mercaptoethane 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.

Half Life

The elimination half-life is 0.36 hours for mesna and 1.17 hours for dimesna.

Clearance

Plasma clearance of mesna = 1.23 L/h/kg

Elimination Route

Within 24 hours, approximately 32% of administered dose is eliminated in the urine as mesna while 33% is eliminated as dimesna.

Innovators Monograph

You find simplified version here 2-Mercaptoethane

*** Taking medicines without doctor's advice can cause long-term problems.
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