Mesalamine

Base Information

• Chemical Name: Mesalamine
• CAS No.: 89-57-6
• Deprecated CAS: 61513-32-4
• Molecular Formula: C7H7NO3
• Molecular Weight: 153.137
• Hs Code.: 29225000
• European Community (EC) Number: 201-919-1
• NSC Number: 759301,38877
• UNII: 4Q81I59GXC
• DSSTox Substance ID: DTXSID5024506
• Nikkaji Number: J32.511B
• Wikipedia: Mesalazine
• Wikidata: Q412479
• NCI Thesaurus Code: C29249
• RXCUI: 52582
• Pharos Ligand ID: 6T8QBZGXYBS5
• Metabolomics Workbench ID: 42646
• ChEMBL ID: CHEMBL704
• Mol file: 89-57-6.mol

Synonyms:5 Aminosalicylate;5 Aminosalicylic Acid;5-Aminosalicylate;5-Aminosalicylic Acid;Asacol;Asacolon;Ascolitin;Canasa;Claversal;Fivasa;Hydrochloride, Mesalamine;Lixacol;m Aminosalicylic Acid;m-Aminosalicylic Acid;Mesalamine;Mesalamine Hydrochloride;Mesalamine Monosodium Salt;Mesalazine;Mesasal;meta Aminosalicylic Acid;meta-Aminosalicylic Acid;Monosodium Salt, Mesalamine;Novo 5 ASA;Novo-5 ASA;Pentasa;Rowasa;Salofalk

Chemical Property of Mesalamine

Chemical Property:

• Appearance/Colour: Off-white crystals
• Vapor Pressure: 3.01E-07mmHg at 25°C
• Melting Point: 275-280 °C (dec.)(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 403.9 °C at 760 mmHg
• PKA: 2.74, 5.84(at 25℃)
• Flash Point: 198.1 °C
• PSA: 83.55000
• Density: 1.491 g/cm³
• LogP: 1.25380
• Storage Temp.: 2-8°C
• Solubility.: Soluble in dimethyl sulfoxide.
• Water Solubility.: <0.1 g/100 mL at 21℃
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 153.042593085
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

5-?AminosalicylicAcid(Mesalazine) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-52/53
• Safety Statements: 26-36-24/25-61-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Gastrointestinal Agents
• Canonical SMILES: C1=CC(=C(C=C1N)C(=O)O)O
• Recent ClinicalTrials: Administration of Hydroxychloroquine (Plaquenil) to African Americans and Hispanics for the Treatment of Mild to Severe Ulcerative Colitis
• Recent EU Clinical Trials: Intestinal disposition of mesalazine in healthy volunteers
• Recent NIPH Clinical Trials: The investigation for maintenance therapy by mesalazine enema after remission induction by budesonide form enema in patients with ulcerative colitis: Multicenter randomized controlled study
• Description: 5-Aminosalicylic acid (5-ASA) 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. 50%. In ionophore-stimulated human leukocytes, 400 μM 5-ASA reduces LTB4 production approximately 20%. 5-ASA does not inhibit 15-hydroxy PGDH at concentrations up to 50 μM. Fisalamine is an intestinal metabolite of sulfasalazine useful in the treatment of ulcerative colitis and to a lesser degree in the management of Crohn’s disease. Administered as a suppository, it appears to lack the hypersensitivity-type side effects of sulfasalazine.
• Uses: In manufacture of light-sensitive paper, azo and sulfur dyes. The active metabolite of Sulfasalazine (S699084). Anti-inflammatory (gastrointestinal). peroxidase substrate For the treatment of active ulcerative proctitis. 5-Aminosalicylic acid is used in the preparation of gastrointestinal anti-inflammatory agents. It is a metabolite of sulfasalazine. It acts as a drug involved in the treatment of Crohn?s disease and ulcerative colitis. Further, it is used to make dyes and light-sensitive papers.
• Therapeutic Function: Antibacterial
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Mesalamine

There total 62 articles about Mesalamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.6%

5-nitrosalicylic acid (96-97-9) → 5-Aminosalicylic Acid (89-57-6)

Guidance literature:

5-nitrosalicylic acid; at 95 - 98 ℃; pH=2;

With sodium hydroxide; at 85 - 95 ℃; for 2.5h; pH=11.5 - 12; Product distribution / selectivity;

Reference yield: 90.5%

carbon dioxide (124-38-9,18923-20-1) + 4-amino-phenol (123-30-8) → 5-Aminosalicylic Acid (89-57-6)

Guidance literature:

4-amino-phenol; With sodium hydroxide; at 130 - 150 ℃;

carbon dioxide; under 67506.8 Torr; Autoclave; Heating;

With sulfuric acid; pH=2 - 3;

Reference yield: 90.0%

carbon dioxide (124-38-9,18923-20-1) + 4-acetaminophenol (103-90-2,8055-08-1) → 5-Aminosalicylic Acid (89-57-6)

Guidance literature:

carbon dioxide; 4-acetaminophenol; With potassium hydroxide; at 220 ℃; for 1h; under 37503.8 Torr;

With hydrogenchloride; water; at 80 ℃; pH=4; Reagent/catalyst; Temperature; Pressure; Time;

upstream raw materials:

2-hydroxy-5-phenylazobenzoic acid methyl ester

5-nitrosalicylic acid

p-aminophenol hydrochloride

methylammonium carbonate

Downstream raw materials:

pimelaldehyde

2-hydroxy-5-iodobenzoic acid

2,5-dihydroxybenzoic acid.

5-amino-2-hydroxy-3-sulfobenzoic acid

Refernces

• 1、 Abe, Kanae,Nakada, Akinobu,Matsumoto, Takeshi,Uchijyo, Daiki,Mori, Hirotoshi,Chang, Ho-Chol. "Functional Group-Directed Photochemical Reactions of Aromatic Alcohols, Amines, and Thiols Triggered by Excited-State Hydrogen Detachment: Additive-free Oligomerization, Disulfidation, and C(sp2)-H Carboxylation with CO2". . p. 959 - 969. Retrieved 2020/12/23.
• 2、 -. "One-pot catalytic synthesis method of 5-aminosalicylic acid". Paragraph 0013; 0026-0049. . Retrieved 2020/08/27.