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    Mesna: Mesna, Sold Under The Brand

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    Andry Hamdani
    Mesna is a medication used to decrease the risk of bleeding from the bladder in those taking cyclophosphamide or ifosfamide for cancer chemotherapy. It works by altering the breakdown products of these chemotherapy drugs in the urine, making them less toxic. Common side effects include headaches, vomiting, and rash. Mesna is administered orally or intravenously.

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    Mesna: Mesna, Sold Under The Brand

    Uploaded by

    Andry Hamdani
    116 views17 pages
    Mesna is a medication used to decrease the risk of bleeding from the bladder in those taking cyclophosphamide or ifosfamide for cancer chemotherapy. It works by altering the breakdown products of these chemotherapy drugs in the urine, making them less toxic. Common side effects include headaches, vomiting, and rash. Mesna is administered orally or intravenously.

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    Mesna

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    Mesna is a medication used to decrease the risk of bleeding from the bladder in those taking cyclophosphamide or ifosfamide for cancer chemotherapy. It works by altering the breakdown products of these chemotherapy drugs in the urine, making them less toxic. Common side effects include headaches, vomiting, and rash. Mesna is administered orally or intravenously.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    116 views17 pages

    Mesna: Mesna, Sold Under The Brand

    Uploaded by

    Andry Hamdani
    Mesna is a medication used to decrease the risk of bleeding from the bladder in those taking cyclophosphamide or ifosfamide for cancer chemotherapy. It works by altering the breakdown products of these chemotherapy drugs in the urine, making them less toxic. Common side effects include headaches, vomiting, and rash. Mesna is administered orally or intravenously.

    Copyright:

    © All Rights Reserved
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    of 17

    Mesna

    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.[1]
    It is used either by mouth or
    injection into a vein.[1]
    Mesna

    Clinical data
    Pronunciation /ˈmɛznə/
    AHFS/Drugs.com Monograph

    Pregnancy AU: B1
    category
    US: B (No risk in
    non-human
    studies)
    Routes of by mouth,
    administration
    intravenous
    ATC code R05CB05
    (WHO ) V03AF01
    (WHO )

    Legal status
    Legal status AU: S4
    (Prescription
    only)
    UK: POM
    (Prescription
    only)
    US: ℞-only

    Pharmacokinetic data
    Bioavailability 45–79% (by
    mouth)
    Metabolism Oxidised in
    circulation
    Biological half- 0.36–8.3 hours
    life
    Excretion kidney

    Identifiers

    IUPAC name
    sodium 2-sulfanylethanesulfonate

    CAS Number 19767-45-4


    PubChem CID 29769
    ChemSpider 27663
    UNII NR7O1405Q9
    KEGG D01459
    ChEMBL CHEMBL975
    ECHA InfoCard 100.039.336

    Chemical and physical data


    Formula C2H5NaO3S2
    Molar mass 164.181 g/mol
    3D model Interactive
    (JSmol)
    image

    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
    Key:XOGTZOOQQBDUSI-UHFFFAOYSA-M

    (what is this?)  (verify)

    Common side effects include


    headache, vomiting,
    sleepiness, loss of appetite,
    cough, rash, and joint pain.[1]
    Serious side effects include
    allergic reactions.[1] Use
    during pregnancy appears to
    be safe for the baby but this
    use has not been well
    studied.[2] Mesna is a
    organosulfur compound.[3] It
    works by altering the
    breakdown products of
    cyclophosphamide and
    ifosfamide found in the urine
    making them less toxic.[1]

    Mesna was approved for


    medical use in the United
    States in 1988.[1] It is on the
    World Health Organization's
    List of Essential Medicines, the
    most effective and safe
    medicines needed in a health
    system.[4] The wholesale cost
    in the developing world is
    about 3.50 USD per 400 mg
    vial.[5] In the United Kingdom
    this amount costs the NHS
    about £3.95.[6]

    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.[7] 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[8] and Mistabronco.

    Administration
    It is administered
    intravenously or orally (per
    mouth).[9] 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
    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.[7]
    This conjugation reaction
    inactivates the urotoxic
    compounds to harmless
    metabolites. The metabolites
    are then excreted in the
    urine.[10]
    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. "Mesna" . The American
    Society of Health-System
    Pharmacists. Retrieved 8
    December 2016.
    2. "Mesna (Mesnex) Use
    During Pregnancy" .
    www.drugs.com. Retrieved 20
    December 2016.
    3. Patwardhan, Bhushan;
    Chaguturu, Rathnam (2016).
    Innovative Approaches in Drug
    Discovery:
    Ethnopharmacology, Systems
    Biology and Holistic Targeting .
    Academic Press. p. 53.
    ISBN 9780128018224.
    4. "WHO Model List of
    Essential Medicines (19th
    List)" (PDF). World Health
    Organization. April 2015.
    Retrieved 8 December 2016.
    5. "Mesna" . International
    Drug Price Indicator Guide.
    Retrieved 8 December 2016.
    6. British national formulary :
    BNF 69 (69 ed.). British Medical
    Association. 2015. p. 578.
    ISBN 9780857111562.
    7. Thurston DE (2007).
    Chemistry and Pharmacology
    of Anticancer Drugs . Boca
    Raton: CRC Press/Taylor &
    Francis. pp. 53–54.
    ISBN 978-1-4200-0890-6.
    8. "Mistabron Ampoules" .
    South African Electronic
    Package Inserts. August 1973.
    Retrieved 2008-08-12.
    9. 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 .
    10. Shaw IC, Graham MI
    (1987). "Mesna—a short
    review". Cancer Treat. Rev. 14
    (2): 67–86. PMID 3119211 .
    doi:10.1016/0305-7372(87)9
    0041-7 .

    External links
    BC Cancer Agency
    NIH/MedlinePlus patient
    information
    Mesna at the US National
    Library of Medicine Medical
    Subject Headings (MeSH)
    Retrieved from
    "https://en.wikipedia.org
    /w/index.php?title=Mesna&
    oldid=789461323"

    Last edited 13 days ago…

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