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{{Short description|Chemical compound}}
{{about|the sulfonate|the thiolate MeSNa|Sodium methanethiolate}}
{{about|the sulfonate|the thiolate MeSNa|Sodium methanethiolate}}
{{Drugbox
{{Drugbox
Line 12: Line 13:
| Drugs.com = {{drugs.com|monograph|mesna}}
| Drugs.com = {{drugs.com|monograph|mesna}}
| pregnancy_AU = B1
| pregnancy_AU = B1
| pregnancy_US = B
| legal_AU = S4
| legal_AU = S4
| legal_UK = POM
| legal_UK = POM
| legal_US = Rx-only
| legal_US = Rx-only
| routes_of_administration = by mouth, intravenous
| routes_of_administration = [[Oral administration|By mouth]], intravenous
<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability = 45–79% (by mouth)
| bioavailability = 45–79% (by mouth)
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<!--Chemical data-->
<!--Chemical data-->
| C=2 | H=5 | Na=1 | O=3 | S=2
| C=2 | H=5 | Na=1 | O=3 | S=2
| molecular_weight = 164.181 g/mol
| SMILES = [Na+].[O-]S(=O)(=O)CCS
| SMILES = [Na+].[O-]S(=O)(=O)CCS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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}}
}}
<!-- Definition and medical uses -->
<!-- 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 by mouth or [[intravenous|injection into a vein]].<ref name=AHFS2016/>
'''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 -->
<!-- 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|accessdate=20 December 2016}}</ref> Mesna is a [[organosulfur compound]].<ref>{{cite book|last1=Patwardhan|first1=Bhushan|last2=Chaguturu|first2=Rathnam|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.ca/books?id=K8sHBgAAQBAJ&pg=PA53|language=en}}</ref> It works by altering the breakdown products of cyclophosphamide and ifosfamide found in the urine making them less toxic.<ref name=AHFS2016/>
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 -->
<!-- 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|accessdate= 8 December 2016}}</ref> It is on the [[World Health Organization's List of Essential Medicines]], the most effective and safe medicines needed in a [[health system]].<ref name=WHO19th>{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|accessdate=8 December 2016|date=April 2015}}</ref> The wholesale cost in the [[developing world]] is about 3.50 USD USD per 400&nbsp;mg vial.<ref name=ERC2014>{{cite web|title=Mesna|url=http://erc.msh.org/dmpguide/resultsdetail.cfm?language=english&code=MES400I&s_year=2014&year=2014&str=400%20mg&desc=Mesna&pack=new&frm=AMPOULE&rte=INJ&class_code2=08%2E2%2E&supplement=&class_name=%2808%2E2%2E%29Cytotoxic%20and%20adjuvant%20medicines%3Cbr%3E|website=International Drug Price Indicator Guide|accessdate=8 December 2016}}</ref> In the United Kingdom this amount costs the [[NHS]] about £3.95.<ref name=BNF69>{{cite book|title=British national formulary : BNF 69|date=2015|publisher=British Medical Association|isbn=9780857111562|page=578|edition=69}}</ref>
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 ==
== Medical uses ==
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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 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 | last1 = Thurston | first1 = David E. | name-list-format = vanc | 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&lpg=PA54&ots=aozQs_9oDY&dq=ifosfamide%20mesna%20michael%20addition%20detoxification&pg=PA54#v=onepage&q=ifosfamide%20mesna%20michael%20addition%20detoxification&f=false}}</ref> This reaction is known as a [[Michael addition]]. Mesna also increases urinary excretion of [[cysteine]].
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 ===
=== 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 |accessdate=2008-08-12}}</ref> and Mistabronco.
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 ==
== Administration ==


It is administered [[intravenously]] or orally (per mouth).<ref name="pmid14676103">{{cite journal |vauthors=Mace JR, Keohan ML, Bernardy H, etal |title=Crossover randomized comparison of intravenous versus intravenous/oral mesna in soft tissue sarcoma treated with high-dose ifosfamide |journal=Clin. Cancer Res. |volume=9 |issue=16 Pt 1 |pages=5829–34 |date=December 2003 |pmid=14676103 |doi= |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.
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 ==
== 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 Treat. Rev. | volume = 14 | issue = 2 | pages = 67–86 | year = 1987 | pmid = 3119211 | doi = 10.1016/0305-7372(87)90041-7 }}</ref>
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==
==Names==
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== References ==
== References ==
{{reflist|30em}}
{{Reflist}}


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


{{Cough and cold preparations}}
{{Cough and cold preparations}}
{{Detoxifying agents for antineoplastic treatment}}
{{Detoxifying agents for antineoplastic treatment}}
{{portal bar|Medicine}}


[[Category:Chemotherapeutic adjuvants]]
[[Category:Chemotherapeutic adjuvants]]
[[Category:Thiols]]
[[Category:Thiols]]
[[Category:Expectorants]]
[[Category:Expectorants]]
[[Category:Sodium compounds]]
[[Category:Organic sodium salts]]
[[Category:World Health Organization essential medicines]]
[[Category:World Health Organization essential medicines]]
[[Category:RTT]]
[[Category:Wikipedia medicine articles ready to translate]]
[[Category:Sulfonates]]

Latest revision as of 12:52, 29 September 2023

This article is about the sulfonate. For the thiolate MeSNa, see Sodium methanethiolate.
Mesna
Clinical data
Pronunciation/ˈmɛznə/
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability45–79% (by mouth)
MetabolismOxidised in circulation
Elimination half-life0.36–8.3 hours
Excretionkidney
Identifiers
  • sodium 2-sulfanylethanesulfonate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.039.336 Edit this at Wikidata
Chemical and physical data
FormulaC2H5NaO3S2
Molar mass164.17 g·mol−1
3D model (JSmol)
  • [Na+].[O-]S(=O)(=O)CCS
  • 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
 ☒NcheckY (what is this?)  (verify)

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]

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 an 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.[4]

Medical uses[edit]

Chemotherapy adjuvant[edit]

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.[5] This reaction is known as a Michael addition. Mesna also increases urinary excretion of cysteine.

Other[edit]

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[6] and Mistabronco.

Administration[edit]

It is administered intravenously 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.

Mechanism of action[edit]

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.[5] This conjugation reaction inactivates the urotoxic compounds to harmless metabolites. The metabolites are then excreted in the urine.[8]

Names[edit]

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[edit]

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

References[edit]

  1. ^ a b c d e f "Mesna". The American Society of Health-System Pharmacists. Archived from the original on 11 May 2017. Retrieved 8 December 2016.
  2. ^ "Mesna (Mesnex) Use During Pregnancy". www.drugs.com. Archived from the original on 11 May 2017. Retrieved 20 December 2016.
  3. ^ Patwardhan B, Chaguturu R (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.
  4. ^ 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.
  5. ^ a b Thurston DE (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.
  6. ^ "Mistabron Ampoules". South African Electronic Package Inserts. August 1973. Archived from the original on 2008-10-22. Retrieved 2008-08-12.
  7. ^ Mace JR, Keohan ML, Bernardy H, Junge K, Niebch G, Romeis P, et al. (December 2003). "Crossover randomized comparison of intravenous versus intravenous/oral mesna in soft tissue sarcoma treated with high-dose ifosfamide". Clinical Cancer Research. 9 (16 Pt 1): 5829–5834. PMID 14676103.
  8. ^ Shaw IC, Graham MI (June 1987). "Mesna--a short review". Cancer Treatment Reviews. 14 (2): 67–86. doi:10.1016/0305-7372(87)90041-7. PMID 3119211.

External links[edit]

Retrieved from "https://en.wikipedia.org/w/index.php?title=Mesna&oldid=1177764706"