View source for Mesna

{{Short description|Chemical compound}}
{{about|the sulfonate|the thiolate MeSNa|Sodium methanethiolate}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 462249008
| drug_name = 
| IUPAC_name = sodium 2-sulfanylethanesulfonate
| image = Mesna.svg
| image_class = skin-invert-image
<!--Clinical data-->
| pronounce = {{IPAc-en|ˈ|m|ɛ|z|n|ə}}
| tradename =  
| Drugs.com = {{drugs.com|monograph|mesna}}
| pregnancy_AU  = B1
| legal_AU = S4
| legal_UK = POM
| legal_US = Rx-only
| routes_of_administration = [[Oral administration|By mouth]], intravenous
<!--Pharmacokinetic data-->
| bioavailability = 45–79% (by mouth)
| metabolism = [[Oxidation|Oxidised]] in [[circulatory system|circulation]]
| elimination_half-life = 0.36–8.3 hours
| excretion = [[kidney]]
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 19767-45-4
| ATC_prefix = R05
| ATC_suffix = CB05
| ATC_supplemental =   {{ATC|V03|AF01}}
| PubChem = 29769
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB09110
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 27663
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NR7O1405Q9
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D01459
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 975
<!--Chemical data-->
| C=2 | H=5 | Na=1 | O=3 | S=2
| SMILES = [Na+].[O-]S(=O)(=O)CCS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H6O3S2.Na/c3-7(4,5)2-1-6;/h6H,1-2H2,(H,3,4,5);/q;+1/p-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XOGTZOOQQBDUSI-UHFFFAOYSA-M
}}
<!-- Definition and medical uses -->
'''Mesna''', sold under the brand name '''Mesnex''' among others, is a medication used in those taking [[cyclophosphamide]] or [[ifosfamide]] to decrease the risk of [[hemorrhagic cystitis|bleeding from the bladder]].<ref name=AHFS2016/> It is used either [[Oral administration|by mouth]] or [[intravenous|injection into a vein]].<ref name=AHFS2016/>

<!-- Side effects and mechanism -->
Common side effects include headache, vomiting, sleepiness, loss of appetite, cough, rash, and joint pain.<ref name=AHFS2016/> Serious side effects include [[allergic reactions]].<ref name=AHFS2016/> Use during [[pregnancy]] appears to be safe for the baby but this use has not been well studied.<ref>{{cite web|title=Mesna (Mesnex) Use During Pregnancy|url=https://www.drugs.com/pregnancy/mesna.html|website=www.drugs.com|access-date=20 December 2016|url-status=live|archive-url=https://web.archive.org/web/20170511021816/https://www.drugs.com/pregnancy/mesna.html|archive-date=11 May 2017}}</ref> Mesna is an [[organosulfur compound]].<ref>{{cite book| vauthors = Patwardhan B, Chaguturu R |title=Innovative Approaches in Drug Discovery: Ethnopharmacology, Systems Biology and Holistic Targeting |date=2016 |publisher=Academic Press |isbn=9780128018224 |page=53 |url= https://books.google.com/books?id=K8sHBgAAQBAJ&pg=PA53|language=en|url-status=live|archive-url=https://web.archive.org/web/20161221162023/https://books.google.ca/books?id=K8sHBgAAQBAJ&pg=PA53|archive-date=2016-12-21}}</ref> It works by altering the breakdown products of cyclophosphamide and ifosfamide found in the urine making them less toxic.<ref name=AHFS2016/>

<!-- History, society and culture -->
Mesna was approved for medical use in the United States in 1988.<ref name=AHFS2016>{{cite web|title=Mesna|url=https://www.drugs.com/monograph/mesna.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20170511021753/https://www.drugs.com/monograph/mesna.html|archive-date=11 May 2017}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref>

== Medical uses ==

=== Chemotherapy adjuvant ===

Mesna is used therapeutically to reduce the incidence of [[hemorrhagic cystitis|haemorrhagic cystitis]] and [[hematuria|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 [[carbonyl#.CE.B1.2C.CE.B2-Unsaturated carbonyl compounds|α,β-unsaturated carbonyl]] containing compounds such as acrolein.<ref name="Thurston_2007">{{cite book | vauthors = Thurston DE | title = Chemistry and Pharmacology of Anticancer Drugs | date = 2007 | publisher = CRC Press/Taylor & Francis | location = Boca Raton | isbn = 978-1-4200-0890-6 | pages = 53–54 | url = https://books.google.com/books?id=5uB19xhhyDsC&q=ifosfamide+mesna+michael+addition+detoxification&pg=PA54 | url-status = live | archive-url = https://web.archive.org/web/20160519132854/https://books.google.com/books?id=5uB19xhhyDsC&lpg=PA54&ots=aozQs_9oDY&dq=ifosfamide%20mesna%20michael%20addition%20detoxification&pg=PA54#v=onepage&q=ifosfamide%20mesna%20michael%20addition%20detoxification&f=false | archive-date = 2016-05-19 }}</ref> 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<ref>{{cite web |url=http://home.intekom.com/pharm/ucb/mistabrn.html |title=Mistabron Ampoules |date=August 1973 |publisher=South African Electronic Package Inserts |access-date=2008-08-12 |url-status=dead |archive-url=https://web.archive.org/web/20081022092114/http://home.intekom.com/pharm/ucb/mistabrn.html |archive-date=2008-10-22 }}</ref> and Mistabronco.

== Administration ==

It is administered [[intravenously]] or orally (through the mouth).<ref name="pmid14676103">{{cite journal | vauthors = Mace JR, Keohan ML, Bernardy H, Junge K, Niebch G, Romeis P, Thoma A, Wagner T, Mueller U, Demetri G, Baker LH | display-authors = 6 | title = Crossover randomized comparison of intravenous versus intravenous/oral mesna in soft tissue sarcoma treated with high-dose ifosfamide | journal = Clinical Cancer Research | volume = 9 | issue = 16 Pt 1 | pages = 5829–5834 | date = December 2003 | pmid = 14676103 | url = http://clincancerres.aacrjournals.org/cgi/pmidlookup?view=long&pmid=14676103 }}</ref> 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.<ref name = "Thurston_2007"/>  This conjugation reaction inactivates the urotoxic compounds to harmless metabolites.  The metabolites are then excreted in the urine.<ref name="pmid3119211">{{cite journal | vauthors = Shaw IC, Graham MI | title = Mesna--a short review | journal = Cancer Treatment Reviews | volume = 14 | issue = 2 | pages = 67–86 | date = June 1987 | pmid = 3119211 | doi = 10.1016/0305-7372(87)90041-7 }}</ref>

==Names==
It is marketed by [[Baxter International|Baxter]] as Uromitexan and Mesnex. The name of the substance is an acronym for 2-'''m'''ercapto'''e'''thane '''s'''ulfonate '''Na''' (''Na'' being the chemical symbol for [[sodium]]).

== See also ==
* [[Coenzyme M]]—a coenzyme with the same structure used by methanogenic bacteria

== References ==
{{Reflist}}

== External links ==
* [https://web.archive.org/web/20150314044447/http://www.bccancer.bc.ca/HPI/DrugDatabase/DrugIndexPro/Mesna.htm BC Cancer Agency]
* [https://www.medlineplus.gov/druginfo/meds/a695034.html NIH/MedlinePlus patient information]
* {{MeSH name|Mesna}}

{{Cough and cold preparations}}
{{Detoxifying agents for antineoplastic treatment}}
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[[Category:Chemotherapeutic adjuvants]]
[[Category:Thiols]]
[[Category:Expectorants]]
[[Category:Organic sodium salts]]
[[Category:World Health Organization essential medicines]]
[[Category:Wikipedia medicine articles ready to translate]]
[[Category:Sulfonates]]