Mesna, sold under the brand name Mesnex among others, is a medication used in those taking

cyclophosphamide Cyclophosphamide (CP), also known as cytophosphane among other names, is a medication used as chemotherapy and to suppress the immune system. As chemotherapy it is used to treat lymphoma, multiple myeloma, leukemia, ovarian cancer, breast cancer ...

or ifosfamide to decrease the risk of bleeding from the bladder. It is used either by mouth or injection into a vein. Common side effects include headache, vomiting, sleepiness, loss of appetite, cough, rash, and joint pain. Serious side effects include allergic reactions. Use during pregnancy appears to be safe for the baby but this use has not been well studied. Mesna is an

organosulfur compound Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfu ...

. It works by altering the breakdown products of cyclophosphamide and ifosfamide found in the urine making them less toxic. Mesna was approved for medical use in the United States in 1988. It is on the World Health Organization's List of Essential Medicines.

Medical uses

Chemotherapy adjuvant

Mesna is used therapeutically to reduce the incidence of

haemorrhagic cystitis Hemorrhagic cystitis or haemorrhagic cystitis is an inflammation of the bladder defined by lower urinary tract symptoms that include dysuria, hematuria, and hemorrhage. The disease can occur as a complication of cyclophosphamide, ifosfamide and ra ...

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 Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fa ...

. Mesna assists to detoxify these metabolites by reaction of its

sulfhydryl In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl grou ...

group with α,β-unsaturated carbonyl containing compounds such as acrolein. This reaction is known as a Michael addition. Mesna also increases urinary excretion of

cysteine Cysteine (symbol Cys or C; ) is a semiessential proteinogenic amino acid with the formula . The thiol side chain in cysteine often participates in enzymatic reactions as a nucleophile. When present as a deprotonated catalytic residue, sometime ...

Other

Outside North America, mesna is also used as a mucolytic agent, working in the same way as

acetylcysteine Acetylcysteine, also known as ''N''-acetylcysteine (NAC), is a medication that is used to treat paracetamol overdose and to loosen thick mucus in individuals with chronic bronchopulmonary disorders like pneumonia and bronchitis. It has been used ...

; it is sold for this indication as Mistabron and Mistabronco.

Administration

It is administered intravenously or orally (through the mouth). 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

and ifosfamide. Mesna concentrates in the bladder where

accumulates after administration of chemotherapy and through a Michael addition, forms a conjugate with

and other urotoxic metabolites. This conjugation reaction inactivates the urotoxic compounds to harmless metabolites. The metabolites are then excreted in the urine.

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).

References

External links

BC Cancer Agency

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