Compound: 5-Aminosalicylic acid
SMILES: O=C(O)c1c(O)ccc(c1)N
InChIKey: KBOPZPXVLCULAV-UHFFFAOYSA-N
Synonyms: 5-Aminosalicylic acid, mesalamine, Mesalazine, 89-57-6, 5-Amino-2-hydroxybenzoic acid, 5-ASA, Fisalamine, Lialda, m-Aminosalicylic acid, Benzoic acid, 5-amino-2-hydroxy-, Apriso, Mesalazina, sfRowasa, Asacolitin, Mesalazinum, Iialda, p-Aminosalicylsaeure, Asacol HD, Pentacol, Delzicol, 3-carboxy-4-hydroxyaniline, Mezavant XL, MAX-002, SALICYLIC ACID, 5-AMINO-, NSC-38877, 4Q81I59GXC, CHEBI:6775, DTXSID5024506, 5 Aminosalicylate, DTXCID804506, 4-14-00-02058 (Beilstein Handbook Reference), NSC38877, Ipocol, m Aminosalicylic Acid, 5 Aminosalicylic Acid, Novo 5 ASA, meta Aminosalicylic Acid, meta-Aminosalicylic Acid, Hydrochloride, Mesalamine, Monosodium Salt, Mesalamine, Octasa, Pentasa sr, Coltec ec, Mesren mr, Mesalamine Rectal, ZALDYON, RefChem:6004, A07EC02, sfRowasa Sulfite-Free Formulation, 201-919-1, Pentasa, Asacol, Canasa, Claversal, Salofalk, Rowasa, Mesasal, 5-amino-2-hydroxy-benzoic acid, Lixacol, 5-Amino Salicylic Acid, Mesalamine [USAN], 2-Hydroxy-5-aminobenzoic acid, MFCD00007877, 5-AS, NSC 38877, Mesalazine [INN], 5-?Aminosalicylic Acid (Mesalazine), MLS001424012, mesalamine (USAN), 51481-17-5, CAS-89-57-6, NCGC00016344-03, Mesalazinum [Latin], SMR000145728, 5-amino-2-hydroxybenzoic acid,5-Aminosalicylic acid, F1918-0003, Mesalazina [Spanish], p-Aminosalicylsaeure [German], Mesavancol, Mesavance, Mezavant, Mesalazine MMX, Mesalamine (USP), Pentasa (TN), Salofalk Granu-Stix, Apriso (TN), Asacol (TN), Canasa (TN), Lialda (TN), Rowasa (TN), CCRIS 7334, 5-Amino 2-hydroxy benzoic acid, SR-01000763486, Mesalamine [USAN:USP], EINECS 201-919-1, BRN 2090421, UNII-4Q81I59GXC, 5-amino-2-hydroxybenzoicacid, Mesalazin, 3-amino-6-hydroxybenzoic acid, Fisalamine;, Mesalamine;, Mesalazine;, AI3-15564, Claversal;, Pentasa;, Mesalazine CRS, Asacol;, Asalit;, Rowasa;, HSDB 7512, AJG-501, SPD 476, SPD-476, SPD-480, Mesalamine (TN), Delzicol (TN), Sfrowasa (TN), Mesalamine (Lialda), 5-aminosalicylic_acid, MD-0901, 5-Aminosalicyclic acid, 5-amino-salicylic acid, Mesalamine (5-ASA), 5-Aminosalicylic acid;, MESALAMINE [MI], MESALAZINE [JAN], Prestwick0_001069, Prestwick1_001069, Prestwick2_001069, Prestwick3_001069, MESALAMINE [HSDB], WLN: ZR DQ CVQ, Z-206, MESALAMINE [VANDF], CHEMBL704, Epitope ID:613406, Mesalazine (JP18/INN), EC 201-919-1, cid_4075, MESALAZINE [MART.], MESALAMINE [USP-RS], 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, SCHEMBL343127, SPBio_002969, BPBio1_001164, GTPL2700, orb1310419, orb3139226, SCHEMBL7075986, MESALAMINE [ORANGE BOOK], MESALAZINE [EP IMPURITY], SCHEMBL29354798, 5-Aminosalicylic acid, >=99%, BDBM60918, KBio2_002425, KBio2_004993, KBio2_007561, KBio3_002904, 5-Aminosalicylic acid (5-ASA), MESALAZINE [EP MONOGRAPH], 5-Aminosalicylic Acid (Standard), cMAP_000045, HMS1571E20, HMS2051M21, HMS2090I09, HMS2098E20, HMS3393M21, HMS3649K15, HMS3651M15, HMS3715E20, HMS5079B12, MESALAMINE [USP MONOGRAPH], Pharmakon1600-01505993, SMSSF-0065812, Tox21_110384, Tox21_201610, Tox21_303125, AC8101, BBL013046, EBC-00537, HY-15027R, MSK159016, NSC759301, s1681, SBB052617, Sodium aminosalicylate EP Impurity B, STK301678, Mesalazine for system suitability CRS, AKOS000118959, Tox21_110384_1, AC-2764, CCG-100829, DB00244, FM25111, 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, ST4109571, A0317, A2291, AB00374979, NS00004165, SW197303-4, T0646, EN300-18389, C07138, D00377, AB00374979-09, AB00374979-10, AB00374979_11, AB00374979_12, F065629, Q412479, 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, Mesalazine Working Standard (Secondary Reference Standard), 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
Theoretical properties:
molecular_formula: C7H7NO3
molecular_weight: 153.14 g/mol
exact_mass: 153.042593085 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 11
topological_polar_surface_area: 83.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to pinkish crystals
color: White to pinkish crystals
melting_point: 536 °F (decomposes) (NTP, 1992)
solubility: less than 1 mg/mL at 70 °F (NTP, 1992)
vapor_pressure: 0.00000006 [mmHg]
Descriptions:
pubchem: Mesalamine is a monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position. It has a role as a non-steroidal anti-inflammatory drug. It is a monocarboxylic acid, a monohydroxybenzoic acid, an amino acid, a member of phenols and an aromatic amine. It is functionally related to a salicylic acid. It is a conjugate acid of a mesalaminate(1-).
chebi: A monohydroxybenzoic acid that is salicylic acid substituted by an amino group at the 5-position.
chembl: MESALAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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. It 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. Use in pregnancy and breastfeeding appears safe. In people with a sulfa allergy certain formulations may result in problems. Mesalazine is an aminosalicylate and anti-inflammatory. It works by direct contact with the intestines.
Mesalazine was approved for medical use in the United States in 1987. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2023, it was the 202nd most commonly prescribed medication in the United States, with more than 2 million prescriptions.