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| Clinical data | |
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| Pronunciation | /ˈmɛznə/ |
| AHFS/Drugs.com | Monograph |
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| Routes of administration | By mouth, intravenous |
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| Pharmacokinetic data | |
| Bioavailability | 45–79% (by mouth) |
| Metabolism | Oxidised incirculation |
| Eliminationhalf-life | 0.36–8.3 hours |
| Excretion | kidney |
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| ECHA InfoCard | 100.039.336 |
| Chemical and physical data | |
| Formula | C2H5NaO3S2 |
| Molar mass | 164.17 g·mol−1 |
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Mesna, sold under the brand nameMesnex among others, is a medication used in those takingcyclophosphamide orifosfamide to decrease the risk ofbleeding from the bladder.[1] It is used eitherby mouth orinjection into a vein.[1]
Common side effects include headache, vomiting, sleepiness, loss of appetite, cough, rash, and joint pain.[1] Serious side effects includeallergic reactions.[1] Use duringpregnancy appears to be safe for the baby but this use has not been well studied.[2] Mesna is anorganosulfur 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 theWorld Health Organization's List of Essential Medicines.[4]
Mesna is used therapeutically to reduce the incidence ofhaemorrhagic cystitis andhaematuria when a patient receives ifosfamide or cyclophosphamide for cancer chemotherapy. These two anticancer agents,in vivo, may be converted to urotoxic metabolites, such asacrolein.
Mesna assists to detoxify these metabolites by reaction of itssulfhydryl group withα,β-unsaturated carbonyl containing compounds such as acrolein.[5] This reaction is known as aMichael addition. Mesna also increases urinary excretion ofcysteine.
Outside North America, mesna is also used as amucolytic agent, working in the same way asacetylcysteine; it is sold for this indication as Mistabron[6] and Mistabronco.
It is administeredintravenously or orally (through the mouth).[7] 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.
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 agentscyclophosphamide andifosfamide. Mesna concentrates in the bladder whereacrolein accumulates after administration of chemotherapy and through aMichael addition, forms a conjugate withacrolein and other urotoxic metabolites.[5] This conjugation reaction inactivates the urotoxic compounds to harmless metabolites. The metabolites are then excreted in the urine.[8]
It is marketed byBaxter as Uromitexan and Mesnex. The name of the substance is an acronym for 2-mercaptoethanesulfonateNa (Na being the chemical symbol forsodium).
