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Mesalazine - Wikipedia

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Mesalazine
Clinical data

Trade names	Asacol, Lialda, Pentasa, Delzicol, others^[1]
Other names	mesalamine, 5-aminosalicylic acid, 5-ASA, Mesalamine (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a688021
License data	US DailyMed: Mesalamine
Pregnancy category	AU: C^[2]
Routes of administration	By mouth, rectal
ATC code	A07EC02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)^[3] CA: ℞-only^[4]^[5]^[6] UK: POM (Prescription only)^[7] US: ℞-only^[8]^[9]^[10] EU: Rx-only^[11]
Pharmacokinetic data
Bioavailability	orally: 20–30% absorbed rectally: 10–35%
Metabolism	Rapidly & extensively metabolized intestinal mucosal wall and the liver
Elimination half-life	5 hours after initial dose. At steady state 7 hours
Identifiers
IUPAC name 5-Amino-2-hydroxybenzoic acid
CAS Number	89-57-6^Y
PubChem CID	4075
IUPHAR/BPS	2700
DrugBank	DB00244^Y
ChemSpider	3933^Y
UNII	4Q81I59GXC
KEGG	D00377^Y
ChEBI	CHEBI:6775^Y
ChEMBL	ChEMBL704^Y
CompTox Dashboard (EPA)	DTXSID5024506
ECHA InfoCard	100.001.745
Chemical and physical data
Formula	C₇H₇NO₃
Molar mass	153.137 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	283 °C (541 °F)
SMILES O=C(O)c1cc(ccc1O)N
InChI InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)^Y Key:KBOPZPXVLCULAV-UHFFFAOYSA-N^Y
(verify)

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.^[1] It is generally used for mildly to moderately severe disease.^[1] It is taken by mouth or rectally.^[1] The formulations which are taken by mouth appear to be similarly-effective.^[12]

Common side-effects include headache, nausea, abdominal pain, and fever.^[1] Serious side-effects may include pericarditis, liver problems, and kidney problems.^[1]^[12] Use in pregnancy and breastfeeding appears safe.^[12] In people with a sulfa allergy certain formulations may result in problems.^[1] Mesalazine is an aminosalicylate and anti-inflammatory.^[1]^[12] It works by direct contact with the intestines.^[1]

Mesalazine was approved for medical use in the United States in 1987.^[1]^[8] It is on the World Health Organization's List of Essential Medicines.^[13] It is available as a generic medication.^[1]^[14]^[15]^[16] In 2021, it was the 239th most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[17]^[18]

Medical uses

It is used to treat inflammatory bowel disease, including ulcerative colitis and Crohn's disease (effective only in colonic diseases).^[1]

In 2022 Germany introduced guidance to use mesalamine to treat acute uncomplicated diverticulitis.^[19]

Side-effects

Most often reported side-effects are gastrointestinal (GI) (but may also include headache), including: nausea, diarrhea, and abdominal pain.^[7]

Very rarely, use of mesalazine has been associated with an exacerbation of the symptoms of colitis, Stevens Johnson syndrome, and erythema multiforme.^[7]

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,^[7] people with kidney disease,^[7] or people who are allergic to aspirin.^[7]

Chemistry

Mesalazine is the active moiety of sulfasalazine, which is metabolized to sulfapyridine and mesalazine.^[20] It is also the active component of the prodrug balsalazide along with the inert carrier molecule 4-aminobenzoyl-beta-alanine.^[21] It is in the category of disease-modifying antirheumatic drugs (DMARDs) family of medications.^[22] It is unclear exactly how it works.^[22] Mesalazine is claimed to be a PPAR-γ agonist.^[23]

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.^[24] It appears to act locally on colonic mucosa.^[25]

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). ^[26]^[27]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l "Mesalamine Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists.
^ "Mesalamine Use During Pregnancy". Drugs.com. 18 September 2018. Retrieved 30 December 2019.
^ "Mesalazine Sun/ Mesalz (Sun Pharma ANZ Pty Ltd)". Therapeutic Goods Administration (TGA). 13 January 2023. Retrieved 9 April 2023.
^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
^ "Regulatory Decision Summary for Mezera". Drug and Health Products Portal. 5 February 2024. Retrieved 2 April 2024.
^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Retrieved 17 April 2024.
^ ^a ^b ^c ^d ^e ^f "Asacol 400mg MR Tablets - Summary of Product Characteristics (SmPC)". (emc). 14 April 2016. Retrieved 30 December 2019.
^ ^a ^b "Asacol HD- mesalamine tablet, delayed release". DailyMed. 15 April 2018. Retrieved 30 December 2019.
^ "Pentasa- mesalamine capsule". DailyMed. 8 November 2021. Retrieved 17 May 2022.
^ "Lialda- mesalamine tablet, delayed release". DailyMed. 8 November 2021. Retrieved 17 May 2022.
^ Human Medicines Evaluation Division (15 October 2020). "Active substance: mesalazine" (PDF). List of nationally authorised medicinal products. European Medicines Agency.
^ ^a ^b ^c ^d British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 39–41. ISBN 9780857113382.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
^ "ANDA Approval Reports - 2017 First Generic Drug Approvals". Food and Drug Administration (FDA). 3 November 2018. Retrieved 8 April 2019.
^ "2022 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Mesalamine - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
^ Peery AF (12 November 2022). "New German guidelines for the management of diverticulitis". United European Gastroenterology Journal. 10 (9): 913–914. doi:10.1002/ueg2.12331. PMC 9731652. PMID 36302089.
^ Finkel R, Clark MA, Cubeddu LX (2009). Lippincott's Illustrated Reviews: Pharmacology (Fourth ed.). Lippincott Williams & Wilkins. ISBN 978-0-7817-7155-9.
^ "Balsalazide: increasing the choice for patients with ulcerative colitis". Drugs & Therapy Perspectives. 19 (1–4): 1–4. 2003. doi:10.2165/00042310-200319100-00001. S2CID 195230977.
^ ^a ^b "Sulfasalazine". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
^ Cevallos SA, Lee JY, Velazquez EM, Foegeding NJ, Shelton CD, Tiffany CR, et al. (January 2021). Ehrt S (ed.). "5-Aminosalicylic Acid Ameliorates Colitis and Checks Dysbiotic Escherichia coli Expansion by Activating PPAR-γ Signaling in the Intestinal Epithelium". mBio. 12 (1): e03227–20. doi:10.1128/mBio.03227-20. PMC 7845635. PMID 33468700.
^ Nakashima J, Preuss CV (2022). "Mesalamine (USAN)". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 31869178. Retrieved 1 September 2022.
^ Iacucci M, de Silva S, Ghosh S (February 2010). "Mesalazine in inflammatory bowel disease: a trendy topic once again?". Canadian Journal of Gastroenterology. 24 (2): 127–133. doi:10.1155/2010/586092. PMC 2852235. PMID 20151072.
^ "Substance Name: Mesalamine [USAN:USP]". ChemIDplus. Retrieved 2 October 2020.
^ "Mesalamine Uses, Side Effects & Warnings". Drugs.com. 30 August 2019. Retrieved 2 October 2020.

v t e Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)
Rehydration	Oral rehydration therapy
Intestinal anti-infectives	Antibiotics Amphotericin B Colistin Fidaxomicin Kanamycin Natamycin Neomycin Nystatin Paromomycin Polymyxin B Rifaximin Streptomycin Vancomycin Sulfonamides Phthalylsulfathiazole Succinylsulfathiazole Sulfaguanidine Nitrofuran Nifuroxazide Nifurzide Imidazole Miconazole Arsenical Acetarsol Oxyquinoline Broxyquinoline
Intestinal adsorbents	Charcoal Bismuth (including bismuth subsalicylate, known as Pepto-Bismol) Pectin Kaolin Crospovidone Attapulgite Diosmectite
Antipropulsives (opioids)	Opium tincture (laudanum) Codeine Morphine Camphorated opium tincture (paregoric) crosses BBB: Diphenoxylate (+atropine) Difenoxin does not cross BBB: Eluxadoline Loperamide^# (+simethicone)
Intestinal anti-inflammatory agents	corticosteroids acting locally Prednisolone^# Hydrocortisone Prednisone Betamethasone^# Tixocortol Budesonide Beclometasone antiallergic agents, excluding corticosteroids Cromoglicic acid Aminosalicylates Sulfasalazine Mesalazine Olsalazine Balsalazide
Antidiarrheal micro-organisms	Escherichia coli Saccharomyces boulardii
Other antidiarrheals	Albumin tannate Bismuth subsalicylate Ceratonia Crofelemer Octreotide Racecadotril Kaopectate
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)

DP₁Tooltip Prostaglandin D2 receptor 1	Agonists: Prostaglandin D₂ Treprostinil Antagonists: Asapiprant Laropiprant Vidupiprant
DP₂Tooltip Prostaglandin D2 receptor 2	Agonists: Indometacin Prostaglandin D₂ Antagonists: ADC-3680 AZD-1981 Bay U3405 Fevipiprant MK-1029 MK-7246 QAV-680 Ramatroban Setipiprant Timapiprant TM30089 Vidupiprant

EP (E₂)

EP₁Tooltip Prostaglandin EP1 receptor	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322
EP₂Tooltip Prostaglandin EP2 receptor	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155
EP₃Tooltip Prostaglandin EP3 receptor	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Ricinoleic acid Sulprostone Antagonists: L-798106
EP₄Tooltip Prostaglandin EP4 receptor	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: Grapiprant GW-627368 L-161982 ONO-AE3-208
Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)

IP (I₂)

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Unsorted

Enzyme
(inhibitors)

COX (PTGS)	Salicylic acids: Aloxiprin Aspirin (acetylsalicylic acid) Benorilate (benorylate) Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine (5-aminosalicylic acid) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate (salicylic acid) Salsalate Sodium salicylate Triflusal; Acetic acids: Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin (indomethacin) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac; Propionic acids: Alminoprofen Benoxaprofen Bucloxic acid (blucloxate) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid (tiaprofenate) Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate) Floctafenic acid (floctafenate) Flufenamic acid (flufenamate) Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Morniflumic acid (morniflumate) Niflumic acid (niflumate) Talinflumic acid (talinflumate) Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone; Enolic acids (oxicams): Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam; 4-Aminoquinolines: Antrafenine Floctafenine Glafenine; Quinazolines: Fluproquazone Proquazone; Aminonicotinic acids: Clonixeril Clonixin Flunixin; Sulfonanilides: Flosulide Nimesulide; Aminophenols (anilines): Acetanilide AM-404 (N-arachidonoylaminophenol) Bucetin Paracetamol (acetaminophen) Parapropamol Phenacetin Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib; Others/unsorted: Anitrazafen Clobuzarit Curcumin DuP-697 FK-3311 Flumizole FR-122047 Glimepiride Hyperforin Itazigrel L-655240 L-670596 Licofelone Menatetrenone (vitamin K₂) NCX-466 NCX-4040 NS-398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC-236 SC-560 SC-58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin
PGD₂STooltip Prostaglandin D synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
PGESTooltip Prostaglandin E synthase	HQL-79
PGFSTooltip Prostaglandin F synthase	Bimatoprost
PGI₂STooltip Prostacyclin synthase	Tranylcypromine
TXASTooltip Thromboxane A synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Receptor/signaling modulators; Leukotriene signaling modulators

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