5-Aminosalicylic acid, also known as mesalamine or mesalazine, is an anti-inflammatory drug primarily used in the treatment of inflammatory bowel diseases, including ulcerative colitis and Crohn’s disease.
5-Aminosalicylic acid is a derivative of salicylic acid, with an additional amine group at the fifth position of the benzene ring, which contributes to its therapeutic properties.
5-Aminosalicylic acid exerts its effects by inhibiting the production of inflammatory cytokines and reducing oxidative stress within the gastrointestinal tract.
CAS Number: 89-57-6
Molecular Formula: C7H7NO3
Molecular Weight: 153.14
EINECS Number: 201-919-1
Synonyms: 5-Aminosalicylic acid, mesalamine, Mesalazine, 89-57-6, 5-Amino-2-hydroxybenzoic acid, Pentasa, Asacol, Canasa, 5-ASA, Claversal, Rowasa, m-Aminosalicylic acid, Salofalk, Lialda, Fisalamine, Apriso, Mesasal, Benzoic acid, 5-amino-2-hydroxy-, Mesalazina, sfRowasa, Asacolitin, Mesalazinum, Lixacol, Iialda, p-Aminosalicylsaeure, Asacol HD, Pentacol, 5-amino-2-hydroxy-benzoic acid, Mesalamine [USAN], Mesalazinum [Latin], Delzicol, 3-carboxy-4-hydroxyaniline, 5-Amino Salicylic Acid, 2-Hydroxy-5-aminobenzoic acid, MAX-002, SALICYLIC ACID, 5-AMINO-, MFCD00007877, NSC 38877, NSC-38877, CCRIS 7334, EINECS 201-919-1, UNII-4Q81I59GXC, Mesalazine [INN], BRN 2090421, 4Q81I59GXC, CHEBI:6775, DTXSID5024506, AI3-15564, HSDB 7512, SPD 476, Mesalamine [USAN:USP], 5-?Aminosalicylic Acid (Mesalazine), MLS001424012, DTXCID804506, EC 201-919-1, 4-14-00-02058 (Beilstein Handbook Reference), NSC38877, mesalamine (USAN), Mesalazinum (Latin), 51481-17-5, CAS-89-57-6, NCGC00016344-03, SMR000145728, Mesalamine (USAN:USP), MESALAZINE (MART.), MESALAZINE [MART.], MESALAMINE (USP-RS), MESALAMINE [USP-RS], 5-amino-2-hydroxybenzoic acid,5-Aminosalicylic acid, m Aminosalicylic Acid, Mesalazina [Spanish], MESALAZINE (EP IMPURITY), MESALAZINE [EP IMPURITY], 5 Aminosalicylic Acid, p-Aminosalicylsaeure [German], MESALAZINE (EP MONOGRAPH), MESALAZINE [EP MONOGRAPH], Mesavancol, MESALAMINE (USP MONOGRAPH), MESALAMINE [USP MONOGRAPH], Mesavance, Mezavant, meta Aminosalicylic Acid, meta-Aminosalicylic Acid, Mesalazine MMX, Mezavant XL, Mesalamine (USP), Pentasa (TN), Salofalk Granu-Stix, Apriso (TN), Asacol (TN), Canasa (TN), Lialda (TN), Rowasa (TN), 5-AS, 5-Amino 2-hydroxy benzoic acid, SR-01000763486, 5-amino-2-hydroxybenzoicacid, Mesalamine Rectal, AJG-501, SPD-476, SPD-480, Mesalamine (TN), Delzicol (TN), Sfrowasa (TN), Mesalamine (Lialda), ZALDYON, 5-aminosalicylic_acid, MD-0901, 5-Aminosalicyclic acid, 5-amino-salicylic acid, MESALAMINE [MI], MESALAZINE [JAN], Prestwick0_001069, Prestwick1_001069, Prestwick2_001069, Prestwick3_001069, MESALAMINE [HSDB], WLN: ZR DQ CVQ, Z-206, MESALAMINE [VANDF], CHEMBL704, Mesalazine (JP17/INN), cid_4075, MESALAZINE [WHO-DD], Oprea1_847633, SCHEMBL31297, 3amino-6-hydroxybenzoic acid, BSPBio_001058, KBioGR_002425, KBioSS_002431, MLS000758287, 5-Aminosalicylic acid, 95%, 5-Aminosalicylic acid, tablet, BIDD:GT0811, 3-amino-6-hydroxybenzoic acid, SPBio_002969, BPBio1_001164, GTPL2700, sfRowasaSulfite-Free Formulation, MESALAMINE [ORANGE BOOK], SCHEMBL18038934, 5-Aminosalicylic acid, >=99%, BDBM60918, KBio2_002425, KBio2_004993, KBio2_007561, KBio3_002904, 5-Aminosalicylic acid (5-ASA), A07EC02, 5-Aminosalicylic Acid (Standard), cMAP_000045, HMS1571E20, HMS2051M21, HMS2090I09, HMS2098E20, HMS3393M21, HMS3649K15, HMS3651M15, HMS3715E20, Pharmakon1600-01505993, BCP05326, Tox21_110384, Tox21_201610, Tox21_303125, AC8101, BBL013046, HY-15027R, NSC759301, s1681, STK301678, AKOS000118959, Tox21_110384_1, AC-2764, BCP9000175, CCG-100829, DB00244, HS-0100, NC00079, NSC-759301, NCGC00016344-01, NCGC00016344-02, NCGC00016344-04, NCGC00016344-05, NCGC00016344-07, NCGC00090934-01, NCGC00090934-02, NCGC00257142-01, NCGC00259159-01, 5-amino-2-hydroxobenzoic acid monohydrate, BP-13074, DA-70181, HY-15027, SY002854, 5-Aminosalicylic acid, analytical standard, 5-Amino-2-hydroxybenzene-1-carboxylic Acid, A0317, A2291, AB00374979, NS00004165, SW197303-4, EN300-18389, C07138, D00377, AB00374979-09, AB00374979-10, AB00374979_11, AB00374979_12, Q412479, Q-201355, SR-01000763486-3, SR-01000763486-4, SR-01000763486-9, BRD-K28849549-001-11-8, BRD-K28849549-001-12-6, BRD-K28849549-001-13-4, Z57127471, F1918-0003, Mesalazine, European Pharmacopoeia (EP) Reference Standard, Mesalamine, United States Pharmacopeia (USP) Reference Standard, Mesalamine, Pharmaceutical Secondary Standard; Certified Reference Material, InChI=1/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11, Mesalazine for system suitability, European Pharmacopoeia (EP) Reference Standard, 5-Aminosalicylic acid, 98.5%, IKK inhibitor;2-HYDROXY-5-AMINOBENZOIC ACID;3-Carboxy-4-hydroxyaniline;5-AMINO-2-HYDROXYBENZOIC ACID;5-AMINOSALICYLIC ACID;5-ASA;5-AS;rowasa
5-Aminosalicylic acid use in pregnancy and breastfeeding appears safe.
In people with a sulfa allergy certain formulations may result in problems.
5-Aminosalicylic acid is an aminosalicylate and anti-inflammatory.
Unlike corticosteroids or systemic immunosuppressants, 5-Aminosalicylic acid is locally active in the intestinal mucosa, making it a first-line treatment option for mild to moderate cases of ulcerative colitis.
5-Aminosalicylic acid is commonly administered in oral or rectal formulations, including tablets, capsules, suppositories, and enemas, depending on the severity and location of the inflammation.
Additionally, 5-Aminosalicylic acid is often prescribed as a maintenance therapy to prevent disease relapse and sustain remission in patients with chronic inflammatory conditions affecting the digestive system.
Mesalazine, also known as mesalamine or 5-Aminosalicylic acid, is a medication used to treat inflammatory bowel disease, including ulcerative colitis and Crohn's disease.
5-Aminosalicylic acid is generally used for mildly to moderately severe disease.
It is taken by mouth or rectally.
The formulations which are taken by mouth appear to be similarly-effective.
Common side-effects include headache, nausea, abdominal pain, and fever.
Serious side-effects may include pericarditis, liver problems, and kidney problems.
5-Aminosalicylic acid works by direct contact with the intestines.
5-Aminosalicylic acid was approved for medical use in the United States in 1987.
It is on the World Health Organization's List of Essential Medicines.
5-Aminosalicylic acid is available as a generic medication.
In 2021, it was the 239th most commonly prescribed medication in the United States, with more than 1 million prescriptions.
5-Aminosalicylic acid, also known as mesalazine or mesalamine, is a metabolite and potential pharmacologically active component of sulphasalazine, a drug used in the treatment of Crohn’s disease and ulcerative colitis.
However, the mechanism by which this drug works has not been established.
In whole blood assays, 5-ASA proves to be a weak, non-selective inhibitor of both COX-1 and COX-2 with IC50 values of 410 and 61 μM, respectively.
In ionophore-stimulated colonic mucosal cells, 1 mM 5-ASA does not inhibit prostaglandin E2 (PGE2) production, but does reduce leukotriene B4 (LTB4) synthesis approx.
In ionophore-stimulated human leukocytes, 400 μM 5-ASA reduces LTB4 production approximately 20%.
5-Aminosalicylic acid does not inhibit 15-hydroxy PGDH at concentrations up to 50 μM.
5-Aminosalicylic acid is a monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.
5-Aminosalicylic acid has a role as a non-steroidal anti-inflammatory drug.
It is an aromatic amine, an amino acid, a member of phenols, a monocarboxylic acid and a monohydroxybenzoic acid.
5-Aminosalicylic acid is functionally related to a salicylic acid.
It is a conjugate acid of a mesalaminate(1-).
5-Aminosalicylic acid is a first-line medicine, used to treat inflammatory bowel diseases like ulcerative colitis (UC).
It has a high-efficiency rate in maintenance and induction of remission.
5-Aminosalicylic acid is an active component of sulfasalazine and also consists of the carbohydrate polymer, inulin.
5-Aminosalicylic acid might exhibit anti-oxidant activity to lessen tissue injury.
5-Aminosalicylic acid is vital for the prevention of T cell activation and proliferation.
It negatively regulates cyclooxygenase and lipoxygenase pathways and lowers the formation of prostaglandins and leukotrienes.
5-Aminosalicylic acid stimulates the membranous expression of E-cadherin and boosts intercellular adhesion.
5-Aminosalicylic acid derivatives are a class of drugs used to treat active ulcerative colitis (a condition which causes swelling and sores in the lining of the colon [large intestine] and rectum), mild-to-moderate Crohn's disease (a chronic inflammatory disease of the intestines, especially the colon and ileum, associated with ulcers and fistulae), and ulcerative proctitis (a mild form of ulcerative colitis).
They are also indicated to reduce inflammation and pain in rheumatoid arthritis (a chronic progressive disease, causing inflammation in the joints resulting in painful deformity and immobility) and to treat tuberculosis in combination with other active antitubercular medications.
Inflammatory diseases cause excessive production of chemicals such as “prostaglandins” (produced by the enzymes, cyclooxygenase, and lipoxygenase) responsible for inflammation in the colon.
5-Aminosalicylic acid derivatives work by blocking the activity of cyclooxygenase and lipoxygenase, thereby reducing the production of prostaglandins.
5-aminosalicylic acid derivatives are anti-inflammatory drugs that help to reduce symptoms of ulcerative colitis such as diarrhea, rectal bleeding, and stomach pain.
5-Aminosalicylic acid derivatives are administered via the oral route, typically three times a day with or without food, and as a suppository and an enema to be used in the rectum typically once a day at bedtime.
Aminosalicylates are anti-inflammatory agents used to treat inflammatory bowel disease and some forms of arthritis.
They work by inhibiting the production of cyclo-oxygenase and prostaglandin, thromboxane synthetase, platelet activating factor synthetase, and interleukin-1 by macrophages so reduces the acute inflammatory response in inflammatory bowel disease.
5-Aminosalicylic acid, often referred to as mesalamine or mesalazine, is an anti-inflammatory drug widely used in the management of chronic inflammatory bowel diseases, such as ulcerative colitis and Crohn’s disease.
It is structurally related to salicylic acid but contains an amino group at the fifth position on the benzene ring, which enhances its anti-inflammatory properties.
This compound primarily works by inhibiting the production of pro-inflammatory mediators, such as leukotrienes and prostaglandins, thereby reducing inflammation and preventing damage to the intestinal lining.
One of the key advantages of 5-Aminosalicylic acid is its targeted action within the gastrointestinal tract, where it acts locally on the intestinal mucosa without significant systemic absorption.
As a result, it has a lower risk of systemic side effects compared to corticosteroids and other immunosuppressants.
It is available in various formulations, including delayed-release and extended-release oral tablets, granules, rectal suppositories, and enemas, allowing for flexible treatment depending on the severity and location of inflammation.
This medication is commonly used not only for inducing remission in active ulcerative colitis but also as a long-term maintenance therapy to prevent disease relapse.
5-Aminosalicylic acid is especially beneficial for patients with mild to moderate forms of the disease and is often preferred due to its favorable safety profile.
Additionally, some studies suggest that 5-Aminosalicylic acid may have a protective effect against colorectal cancer in patients with chronic inflammatory conditions of the colon.
Melting point: 275-280 °C (dec.) (lit.)
Boiling point: 276.03°C (rough estimate)
Density: 1.3585 (rough estimate)
Bulk density: 300kg/m³
Vapor pressure: 0Pa at 25℃
Refractive index: 1.5500 (estimate)
Flash point: 279-281°C
Storage temp.: 2-8°C
Solubility: Soluble in dimethyl sulfoxide.
pKa: 2.74, 5.84 (at 25℃)
Form: Tablets
Color: Off-white to gray
pH: 4.0-4.1 (0.8g/l, H₂O, 20℃)
pH Range: Non-fluorescence (3.1) to light green fluorescence (4.4)
Water Solubility: <0.1 g/100 mL at 21 ºC
Decomposition: 279-281 ºC
Merck: 14,5904
BRN: 2090421
BCS Class: 4
Stability: Stable. Incompatible with acids, acid anhydrides, acid chlorides, chloroformates, strong oxidizing agents.
Major Application: Detergent, hair dyes, prevention of colorectal cancer, treating inflammatory bowel disease, autoimmune disorders, gastrointestinal inflammation, chemokine-mediated diseases, mucosal tissue disorder, sleep disorders, rectoanal tenesmus, ulcerative colitis.
InChIKey: KBOPZPXVLCULAV-UHFFFAOYSA-N
LogP: 0.98 at 25℃
Off-White to pink crystals, melting point about 280 ℃ (decomposition).
Soluble in hydrochloric acid, slightly soluble in hot water, and slightly bath in cold water or ethanol.
In the manufacture of light-sensitive paper, azo and sulfur dyes.
Poison by intraperitoneal route.
5-Aminosalicylic acid human systemic effects byingestion: hypermotility, diarrhea, dermatitis, increasedbody temperature.
When heated to decomposition it emitstoxic fumes of NOx.
Most often reported side-effects are gastrointestinal (GI) (but may also include headache), including: nausea, diarrhea, and abdominal pain.
Very rarely, use of 5-Aminosalicylic acid has been associated with an exacerbation of the symptoms of colitis, Stevens Johnson syndrome, and erythema multiforme.
5-Aminosalicylic acid is the active moiety of sulfasalazine, which is metabolized to sulfapyridine and mesalazine.
5-Aminosalicylic acid is also the active component of the prodrug balsalazide along with the inert carrier molecule 4-aminobenzoyl-beta-alanine.
It is in the category of disease-modifying antirheumatic drugs (DMARDs) family of medications.
It is unclear exactly how it works.
5-Aminosalicylic acid is claimed to be a PPAR-γ agonist.
Exact mechanism of 5-Aminosalicylic acid is unknown, but is speculated that mesalazine decreases synthesis of prostaglandin and leukotriene, modulating the inflammatory response derived from the cyclooxygenase and lipooxygenase pathways.
It appears to act locally on colonic mucosa.
5-Aminosalicylic acid 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).
An anti-inflammatory agent, structurally related to the salicylates and non-steroidal anti-inflammatory drugs like acetylsalicylic acid, which is active in inflammatory bowel disease 2.
Although demonstrably effective in treating and maintaining remission for ulcerative colitis, mesalazine has historically faced a number of issues regarding its lack of stability as a pharmaceutical agent 1.
Throughout the late seventies and the eighties, important research initiatives developed stable 5-Aminosalicylic acid formulations like the eudragit-S coating of Asacol brand mesalazine and the Pentasa brand's encapsulation of mesalazine within microgranules 1.
In the present day, contemporary research regarding novel methods to stabilize mesalazine continues and interest in the agent's capacity to decrease inflammatory activity and subsequently potentially reduce the risk of colorectal cancer in conditions like ulcerative colitis is maintained.
5-Aminosalicylic acid can vary between individuals, and some patients may require alternative treatments if they do not respond adequately.
Physicians may combine it with other medications, such as corticosteroids or immunomodulators, in cases where inflammation is more severe.
5-Aminosalicylic acid remains an essential component in the management of inflammatory bowel diseases, helping to reduce symptoms, maintain remission, and improve the quality of life for many patients.
Uses Of 5-Aminosalicylic acid:
5-Aminosalicylic acid is used in the preparation of gastrointestinal anti-inflammatory agents.
5-Aminosalicylic acid is a metabolite of sulfasalazine.
It acts as a drug involved in the treatment of Crohn's disease and ulcerative colitis.
5-Aminosalicylic acid is used to make dyes and light-sensitive papers.
5-Aminosalicylic acid has been used to synthesize 5-formyl-aminosalicylate-inulin to quantify its release during in vitro digestion and fermentation and compare the in vitro fermentation properties of the conjugated inulin to native inulin.
It is also used in cell adhesion assay to study its effects on E-cadherin glycosylation and membranous turnover.
This compound is used to evaluate its effects on the neutrophilic inflammation index (NII) phenotype to study the effectiveness of the high cholesterol diet-gut inflammation (HCD-GI) platform.
5-Aminosalicylic acid is a peroxidase substrate suitable for use in ELISA procedures.
This substrate produces a soluble end product that is brown in color and can be read spectrophotometrically at 450 nm.
The reaction may be stopped with 3 N NaOH and read at 550 nm.
5-Aminosalicylic acid, also known as mesalamine or mesalazine, is primarily used in the treatment and management of inflammatory bowel diseases (IBD), particularly ulcerative colitis and, to a lesser extent, Crohn’s disease.
It is commonly prescribed to reduce inflammation in the lining of the intestines and prevent flare-ups, making it an essential component in both the induction and maintenance of remission for patients suffering from these chronic conditions.
One of its most important uses is in the treatment of mild to moderate ulcerative colitis, where it helps to alleviate symptoms such as abdominal pain, diarrhea, rectal bleeding, and urgency by directly targeting inflammation in the colon. By modulating the immune response and inhibiting the production of inflammatory mediators like prostaglandins and leukotrienes, 5-ASA effectively reduces tissue damage and promotes healing of the mucosal lining.
This makes it a valuable first-line therapy for many individuals diagnosed with the disease.
In addition to its role in active disease management, 5-Aminosalicylic acid is widely used as a long-term maintenance therapy to prevent relapses in patients with ulcerative colitis. Since this condition is characterized by periods of remission followed by unpredictable flare-ups, continuous treatment with 5-ASA has been shown to significantly reduce the frequency and severity of these episodes.
Patients who adhere to regular use of the medication often experience prolonged symptom-free periods, which helps improve their overall quality of life.
Although less commonly used for Crohn’s disease, 5-Aminosalicylic acid may still be prescribed for patients with mild cases, particularly when inflammation is localized in the colon. However, its effectiveness in treating Crohn’s disease is somewhat limited compared to ulcerative colitis, and other treatments such as corticosteroids, immunosuppressants, or biologics may be necessary for more severe cases.
Beyond its applications in inflammatory bowel diseases, 5-Aminosalicylic acid has also been explored for its potential protective effects against colorectal cancer, particularly in patients with chronic colonic inflammation.
Some studies suggest that long-term use of 5-Aminosalicylic acid may reduce the risk of dysplasia and colorectal cancer development by inhibiting inflammatory pathways that contribute to carcinogenesis.
5-Aminosalicylic acid is used to treat inflammatory bowel disease, including ulcerative colitis and Crohn's disease (effective only in colonic diseases).
In 2022 Germany introduced guidance to use mesalamine to treat acute uncomplicated diverticulitis.
This section contains uses of this drug that are not listed in the approved professional labeling for the drug but that may be prescribed by your health care professional.
Use this drug for a condition that is listed in this section only if it has been so prescribed by your health care professional.
5-Aminosalicylic acid is sometimes used in combination with other medications for treating certain autoimmune disorders and gastrointestinal conditions that involve chronic inflammation.
Researchers continue to investigate its broader therapeutic potential, including its possible applications in chemokine-mediated diseases, mucosal tissue disorders, and even neuroinflammatory conditions.
5-Aminosalicylic acid plays a crucial role in managing inflammatory bowel diseases by reducing inflammation, maintaining remission, and improving the quality of life for patients.
Its effectiveness, safety profile, and local action within the gastrointestinal tract make it a preferred treatment for many individuals dealing with chronic intestinal inflammation.
Safety Profile Of 5-Aminosalicylic acid:
5-Aminosalicylic acid, while generally considered safe and well-tolerated in most patients, does pose several hazards and potential risks, particularly in individuals with certain medical conditions or those who experience adverse reactions.
One of the primary hazards associated with 5-ASA use is kidney toxicity, as the drug has been linked to cases of interstitial nephritis, a condition that causes inflammation and damage to the kidneys.
Long-term use of 5-Aminosalicylic acid requires regular monitoring of kidney function to prevent potential complications such as renal impairment or failure, especially in patients with pre-existing kidney disease or those taking nephrotoxic medications.
Another significant concern is liver toxicity, as some individuals may experience elevated liver enzymes or hepatotoxicity, particularly those with pre-existing liver disorders.
While this side effect is relatively rare, patients with liver disease should use 5-ASA cautiously under medical supervision, and liver function tests may be required periodically.
Gastrointestinal side effects are also among the most commonly reported hazards of 5-ASA treatment.
Some patients experience nausea, vomiting, abdominal pain, diarrhea, bloating, or flatulence, particularly when starting the medication.
In rare cases, the drug can cause an exacerbation of colitis symptoms, leading to worsening inflammation and discomfort rather than relief.
Hypersensitivity reactions can occur in some individuals, leading to symptoms such as rash, fever, itching, or even severe allergic reactions like anaphylaxis.
In rare instances, patients may develop a condition known as drug-induced lupus, which presents with joint pain, fever, fatigue, and skin rashes.
These reactions typically subside once the medication is discontinued but can be serious if not recognized early.