Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Mesalazine: Difference between pages

{{Short description|Anti-inflammatory medication}}

{{Distinguish|text=[[Aspirin]], also known as acetylsalicylic acid (ASA)}}

{{Use dmy dates|date=November 2022}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

| Watchedfields = changed

| verifiedrevid = 462248957

| alt =

| caption =

| USAN = Mesalamine

<!-- Clinical data -->

| pronounce =

| tradename = Asacol, Lialda, Pentasa, Delzicol, others<ref name=AHFS2019/>

| MedlinePlus = a688021

| DailyMedID = Mesalamine

| pregnancy_AU = C

| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Mesalamine Use During Pregnancy | website=Drugs.com | date=18 September 2018 | url=https://www.drugs.com/pregnancy/mesalamine.html | access-date=30 December 2019}}</ref>

| pregnancy_category=

| routes_of_administration = [[Oral administration|By mouth]], [[Rectal administration|rectal]]

| class =

| ATCvet =

| ATC_prefix = A07

| ATC_suffix = EC02

| ATC_supplemental =

<!-- Legal status -->

| legal_AU = S4

| legal_AU_comment = <ref>{{cite web | title=Mesalazine Sun/ Mesalz (Sun Pharma ANZ Pty Ltd) | website=Therapeutic Goods Administration (TGA) | date=13 January 2023 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/mesalazine-sun-mesalz-sun-pharma-anz-pty-ltd | access-date=9 April 2023}}</ref>

| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->

| legal_BR_comment =

| legal_CA = Rx-only

| legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=Health Canada | date=February 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=24 March 2024}}</ref><ref>{{cite web | title=Regulatory Decision Summary for Mezera | website=Drug and Health Products Portal | date=5 February 2024 | url=https://dhpp.hpfb-dgpsa.ca/review-documents/resource/RDS1710793698140 | access-date=2 April 2024}}</ref><ref>{{cite web | title=Drug and medical device highlights 2018: Helping you maintain and improve your health | website=[[Health Canada]] | date=14 October 2020 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/drug-medical-device-highlights-2018.html | access-date=17 April 2024}}</ref>

| legal_DE = <!-- Anlage I, II, III or Unscheduled-->

| legal_DE_comment =

| legal_NZ = <!-- Class A, B, C -->

| legal_NZ_comment =

| legal_UK = POM

| legal_UK_comment = <ref name="Asacol SmPC" />

| legal_US_comment = <ref name="Asacol FDA label" /><ref name="Pentasa FDA label">{{cite web | title=Pentasa- mesalamine capsule | website=DailyMed | date=8 November 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e39d9a3d-5d3a-4bb6-aab1-fdbb2a598606 | access-date=17 May 2022}}</ref><ref name="Lialda FDA label">{{cite web | title=Lialda- mesalamine tablet, delayed release | website=DailyMed | date=8 November 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3098a080-be86-4265-9818-7fc4beab77b7 | access-date=17 May 2022}}</ref>

| legal_EU = Rx-only

| legal_EU_comment = <ref>{{cite web | author = Human Medicines Evaluation Division | title = Active substance: mesalazine | work = List of nationally authorised medicinal products | publisher = European Medicines Agency | date = 15 October 2020 | url = https://www.ema.europa.eu/documents/psusa/mesalazine-list-nationally-authorised-medicinal-products-psusa/00001990/202002_en.pdf}}</ref>

| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->

| legal_UN_comment =

| legal_status = <!--For countries not listed above-->

<!-- Pharmacokinetic data -->

| bioavailability = orally: 20–30% absorbed<br />rectally: 10–35%

| protein_bound =

| metabolism = Rapidly & extensively metabolized intestinal mucosal wall and the liver

| metabolites =

| onset =

| elimination_half-life = 5 hours after initial dose.<br />At steady state 7 hours

| duration_of_action =

| excretion =

<!-- Identifiers -->

| CAS_supplemental =

| IUPHAR_ligand = 2700

| ChEBI_Ref = {{ebicite|correct|EBI}}

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = mesalamine, 5-aminosalicylic acid, 5-ASA

<!-- Chemical and physical data -->

| IUPAC_name = 5-Amino-2-hydroxybenzoic acid

| C=7 | H=7 | N=1 | O=3

| SMILES = O=C(O)c1cc(ccc1O)N

| StdInChI_comment =

| density =

| density_notes =

| melting_point = 283

| melting_high =

| melting_notes =

| boiling_point =

| boiling_notes =

| solubility =

| sol_units =

| specific_rotation =

<!-- Definition and medical uses -->

'''Mesalazine''', also known as '''mesalamine''' or '''5-aminosalicylic acid''' ('''5-ASA'''), is a medication used to treat [[inflammatory bowel disease]], including [[ulcerative colitis]] and [[Crohn's disease]].<ref name=AHFS2019/> It is generally used for mildly to moderately severe disease.<ref name=AHFS2019/> It is taken by mouth or [[Rectal administration|rectally]].<ref name=AHFS2019/> The formulations which are taken by mouth appear to be similarly-effective.<ref name=BNF76/>

<!-- Side effects and mechanism -->

Common side-effects include headache, nausea, abdominal pain, and fever.<ref name=AHFS2019/> Serious side-effects may include [[pericarditis]], [[liver problems]], and [[kidney problems]].<ref name=AHFS2019/><ref name=BNF76/> Use in [[pregnancy]] and [[breastfeeding]] appears safe.<ref name=BNF76/> In people with a [[sulfa allergy]] certain formulations may result in problems.<ref name=AHFS2019/> Mesalazine is an [[aminosalicylate]] and [[anti-inflammatory]].<ref name=AHFS2019/><ref name=BNF76>{{cite book|title=British national formulary: BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=39–41|edition=76}}</ref> It works by direct contact with the [[intestines]].<ref name=AHFS2019/>

<!--History and culture-->

Mesalazine was approved for medical use in the United States in 1987.<ref name=AHFS2019>{{cite web |title=Mesalamine Monograph for Professionals |url=https://www.drugs.com/monograph/mesalamine.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists }}</ref><ref name="Asacol FDA label">{{cite web | title=Asacol HD- mesalamine tablet, delayed release | website=DailyMed | date=15 April 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f68f68c-58d2-4575-b573-f2e62f95d7e3 | access-date=30 December 2019}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> It is available as a [[generic medication]].<ref name=AHFS2019/><ref>{{cite web |title=ANDA Approval Reports - 2017 First Generic Drug Approvals |url=https://www.fda.gov/Drugs/DevelopmentApprovalProcess/HowDrugsareDevelopedandApproved/DrugandBiologicApprovalReports/ANDAGenericDrugApprovals/ucm597322.htm |website=[[Food and Drug Administration]] (FDA) |date=3 November 2018 |access-date=8 April 2019 }}</ref><ref>{{cite web | title=2022 First Generic Drug Approvals | website=U.S. [[Food and Drug Administration]] (FDA) | date=3 March 2023 | url=https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/2022-first-generic-drug-approvals | archive-url=https://web.archive.org/web/20230630003602/https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/2022-first-generic-drug-approvals | archive-date=30 June 2023 | url-status=live | access-date=30 June 2023}}</ref><ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. [[Food and Drug Administration]] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}</ref> In 2021, it was the 239th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Mesalamine - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Mesalamine | access-date = 14 January 2024}}</ref>

==Medical uses==

{{See also|4-Aminosalicylic acid}}

It is used to treat [[inflammatory bowel disease]], including [[ulcerative colitis]] and [[Crohn's disease]] (effective only in colonic diseases).<ref name=AHFS2019/>

In 2022 Germany introduced guidance to use mesalamine to treat acute uncomplicated [[diverticulitis]].<ref>{{Cite journal|title=New German guidelines for the management of diverticulitis|first=Anne F.|last=Peery|date=November 12, 2022|journal=United European Gastroenterology Journal|volume=10|issue=9|pages=913–914|doi=10.1002/ueg2.12331|pmid=36302089|pmc=9731652}}</ref>

==Side-effects==

Most often reported side-effects are gastrointestinal (GI) (but may also include headache), including: nausea, diarrhea, and abdominal pain.<ref name="Asacol SmPC" />

Very rarely, use of mesalazine has been associated with an exacerbation of the symptoms of [[colitis]], [[Stevens Johnson syndrome]], and [[erythema multiforme]].<ref name="Asacol SmPC">{{cite web | title=Asacol 400mg MR Tablets - Summary of Product Characteristics (SmPC) | website=(emc) | date=14 April 2016 | url=https://www.medicines.org.uk/emc/medicine/12583 | access-date=30 December 2019}}</ref>

=== Pregnancy ===

There is no data on use in pregnant women, but the drug does cross the placenta and is excreted in [[breast milk]]. The drug should not be used in children under two years of age,<ref name="Asacol SmPC" /> people with [[kidney disease]],<ref name="Asacol SmPC" /> or people who are allergic to [[aspirin]].<ref name="Asacol SmPC" />

==Chemistry==

Mesalazine is the active [[Functional group|moiety]] of [[sulfasalazine]], which is metabolized to [[sulfapyridine]] and mesalazine.<ref>{{cite book | vauthors = Finkel R, Clark MA, Cubeddu LX | title = Lippincott's Illustrated Reviews: Pharmacology | year = 2009 | publisher = Lippincott Williams & Wilkins | edition = Fourth | isbn = 978-0-7817-7155-9 }}</ref> It is also the active component of the prodrug [[balsalazide]] along with the inert carrier molecule 4-aminobenzoyl-beta-alanine.<ref>{{cite journal | vauthors = | title = Balsalazide: increasing the choice for patients with ulcerative colitis. | journal = Drugs & Therapy Perspectives | volume = 19 | issue = 1–4 | date = 2003 | pages = 1–4 | doi = 10.2165/00042310-200319100-00001 | s2cid = 195230977 }}</ref> It is in the category of [[disease-modifying antirheumatic drugs]] (DMARDs) family of medications.<ref name=AHFS2016>{{cite web|title=Sulfasalazine|url=https://www.drugs.com/monograph/sulfasalazine.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221012800/https://www.drugs.com/monograph/sulfasalazine.html|archive-date=21 December 2016}}</ref> It is unclear exactly how it works.<ref name=AHFS2016/> Mesalazine is claimed to be a [[PPAR agonist#PPAR-gamma agonists|PPAR-γ agonist]].<ref>{{cite journal | vauthors = Cevallos SA, Lee JY, Velazquez EM, Foegeding NJ, Shelton CD, Tiffany CR, Parry BH, Stull-Lane AR, Olsan EE, Savage HP, Nguyen H, Ghanaat SS, Byndloss AJ, Agu IO, Tsolis RM, Byndloss MX, Bäumler AJ | title = 5-Aminosalicylic Acid Ameliorates Colitis and Checks Dysbiotic Escherichia coli Expansion by Activating PPAR-γ Signaling in the Intestinal Epithelium | journal = mBio | volume = 12 | issue = 1 | pages = e03227–20 | date = January 2021 | pmid = 33468700 | pmc = 7845635 | doi = 10.1128/mBio.03227-20 | veditors = Ehrt S }}</ref>

==Mechanism of action==

Exact mechanism of mesalazine is unknown, but is speculated that mesalazine decreases synthesis of [[prostaglandin]] and [[leukotriene]], modulating the inflammatory response derived from the [[cyclooxygenase]] and [[lipooxygenase]] pathways.<ref>{{cite book | vauthors = Nakashima J, Preuss CV | chapter = Mesalamine (USAN) |year=2022 | chapter-url=http://www.ncbi.nlm.nih.gov/books/NBK551714/ | title = StatPearls |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=31869178 |access-date=1 September 2022 }}</ref> It appears to act locally on colonic mucosa.<ref>{{cite journal | vauthors = Iacucci M, de Silva S, Ghosh S | title = Mesalazine in inflammatory bowel disease: a trendy topic once again? | journal = Canadian Journal of Gastroenterology | volume = 24 | issue = 2 | pages = 127–133 | date = February 2010 | pmid = 20151072 | pmc = 2852235 | doi = 10.1155/2010/586092 | doi-access = free }}</ref>

== Society and culture ==

=== Brand names ===

Mesalazine is sold under various names including Apriso, Asacol, Asacol HD, Canasa, Delzicol, Fivasa, Lialda, Salofalk, Pentasa, Rowasa, Octasa, and Sfrowasa. In Europe, it is sold under the name Salofalk (rectal suppository). <ref>{{cite web | title=Substance Name: Mesalamine [USAN:USP] | website=ChemIDplus | url=https://chem.nlm.nih.gov/chemidplus/rn/89-57-6 | access-date=2 October 2020}}</ref><ref>{{cite web | title=Mesalamine Uses, Side Effects & Warnings | website=Drugs.com | date=30 August 2019 | url=https://www.drugs.com/mtm/mesalamine.html | access-date=2 October 2020}}</ref>

==References==

{{reflist}}

{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}}

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[[Category:Anilines]]

[[Category:Anti-inflammatory agents]]

[[Category:Antioxidants]]

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[[Category:Salicylic acids]]

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[[Category:Drugs developed by Takeda Pharmaceutical Company]]

[[Category:Wikipedia medicine articles ready to translate]]

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