Mesna

Mesna
Names
Pronunciation/ˈmɛznə/
IUPAC name
  • sodium 2-sulfanylethanesulfonate
Clinical data
Drug classOrganosulfur compound[1]
Main usesPrevent toxicity from cyclophosphamide or ifosfamide[2]
Side effectsHeadache, vomiting, sleepiness, loss of appetite, cough, rash, joint pain[2]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • AU: B1
  • US: B (No risk in non-human studies)
    Routes of
    use    		by mouth, intravenous
    Defined daily dose1.2 g [3]
    External links
    AHFS/Drugs.comMonograph
    Legal
    Legal status
    • AU: S4 (Prescription only)
    • UK: POM (Prescription only)
    • US: ℞-only
    Pharmacokinetics
    Bioavailability45–79% (by mouth)
    MetabolismOxidised in circulation
    Elimination half-life0.36–8.3 hours
    Excretionkidney
    Chemical and physical data
    FormulaC2H5NaO3S2
    Molar mass164.17 g·mol−1
    3D model (JSmol)
    SMILES
    • [Na+].[O-]S(=O)(=O)CCS
    InChI
    • InChI=1S/C2H6O3S2.Na/c3-7(4,5)2-1-6;/h6H,1-2H2,(H,3,4,5);/q;+1/p-1 checkY
    • Key:XOGTZOOQQBDUSI-UHFFFAOYSA-M checkY

    Mesna, sold under the brand name Mesnex among others, is a medication used in those taking cyclophosphamide or ifosfamide to decrease the risk of bleeding from the bladder.[2] It is used either by mouth or injection into a vein.[2]

    Common side effects include headache, vomiting, sleepiness, loss of appetite, cough, rash, and joint pain.[2] Serious side effects include allergic reactions.[2] Use during pregnancy appears to be safe for the baby but this use has not been well studied.[4] Mesna is an organosulfur compound.[1] It works by altering the breakdown products of cyclophosphamide and ifosfamide found in the urine making them less toxic.[2]

    Mesna was approved for medical use in the United States in 1988.[2] It is on the World Health Organization's List of Essential Medicines.[5] The wholesale cost in the developing world is about US$3.50 per 400 mg vial.[6] In the United Kingdom this amount costs the NHS about £3.95.[7]

    Medical uses

    Chemotherapy adjuvant

    Mesna is used therapeutically to reduce the incidence of haemorrhagic cystitis and haematuria when a patient receives ifosfamide or cyclophosphamide for cancer chemotherapy. These two anticancer agents, in vivo, may be converted to urotoxic metabolites, such as acrolein.

    Mesna assists to detoxify these metabolites by reaction of its sulfhydryl group with α,β-unsaturated carbonyl containing compounds such as acrolein.[8] This reaction is known as a Michael addition. Mesna also increases urinary excretion of cysteine.

    Other

    Outside North America, mesna is also used as a mucolytic agent, working in the same way as acetylcysteine; it is sold for this indication as Mistabron[9] and Mistabronco.

    Dosage

    The defined daily dose is 1.2 gram (inhaled).[3]

    It is administered intravenously or orally (per mouth).[10] The IV mesna infusions would be given with IV ifosfamide, while oral mesna would be given with oral cyclophosphamide. The oral doses must be double the intravenous (IV) mesna dose due to bioavailability issues. The oral preparation allows patients to leave the hospital sooner, instead of staying four to five days for all the IV mesna infusions.

    Mechanism of action

    Mesna reduces the toxicity of urotoxic compounds that may form after chemotherapy administration. Mesna is a water-soluble compound with antioxidant properties, and is given concomitantly with the chemotherapeutic agents cyclophosphamide and ifosfamide. Mesna concentrates in the bladder where acrolein accumulates after administration of chemotherapy and through a Michael addition, forms a conjugate with acrolein and other urotoxic metabolites.[8] This conjugation reaction inactivates the urotoxic compounds to harmless metabolites. The metabolites are then excreted in the urine.[11]

    Names

    It is marketed by Baxter as Uromitexan and Mesnex. The name of the substance is an acronym for 2-mercaptoethane sulfonate Na (Na being the chemical symbol for sodium).

    See also

    • Coenzyme M—a coenzyme with the same structure used by methanogenic bacteria

    References

    1. 1 2 Patwardhan, Bhushan; Chaguturu, Rathnam (2016). Innovative Approaches in Drug Discovery: Ethnopharmacology, Systems Biology and Holistic Targeting. Academic Press. p. 53. ISBN 9780128018224. Archived from the original on 2016-12-21.
    2. 1 2 3 4 5 6 7 8 "Mesna". The American Society of Health-System Pharmacists. Archived from the original on 11 May 2017. Retrieved 8 December 2016.
    3. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 27 July 2020. Retrieved 17 September 2020.
    4. ↑ "Mesna (Mesnex) Use During Pregnancy". www.drugs.com. Archived from the original on 11 May 2017. Retrieved 20 December 2016.
    5. ↑ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
    6. ↑ "Mesna". International Drug Price Indicator Guide. Archived from the original on 11 May 2017. Retrieved 8 December 2016.
    7. ↑ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 578. ISBN 9780857111562.
    8. 1 2 Thurston, David E. (2007). Chemistry and Pharmacology of Anticancer Drugs. Boca Raton: CRC Press/Taylor & Francis. pp. 53–54. ISBN 978-1-4200-0890-6. Archived from the original on 2016-05-19.
    9. ↑ "Mistabron Ampoules". South African Electronic Package Inserts. August 1973. Archived from the original on 2008-10-22. Retrieved 2008-08-12.
    10. ↑ Mace JR, Keohan ML, Bernardy H, et al. (December 2003). "Crossover randomized comparison of intravenous versus intravenous/oral mesna in soft tissue sarcoma treated with high-dose ifosfamide". Clin. Cancer Res. 9 (16 Pt 1): 5829–34. PMID 14676103. Archived from the original on 2013-01-12. Retrieved 2008-12-18.
    11. ↑ Shaw IC, Graham MI (1987). "Mesna—a short review". Cancer Treat. Rev. 14 (2): 67–86. doi:10.1016/0305-7372(87)90041-7. PMID 3119211.
    Identifiers:
    This article is issued from Offline. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.