| Identification | More | [Name]
5-Aminosalicylic acid | [CAS]
89-57-6 | [Synonyms]
2-HYDROXY-5-AMINOBENZOIC ACID
3-Carboxy-4-hydroxyaniline
5-AMINO-2-HYDROXYBENZOIC ACID
5-AMINOSALICYLIC ACID
5-AS
5-ASA
BENZOIC ACID, 5-AMINO-2-HYDROXY-
IFLAB-BB F1918-0003
LABOTEST-BB LT00134704
M-AMINOSALICYLIC ACID
MESALAMINE
MESALAZINE
rowasa
3-Amino-hydroxybenzoicacid
5-amino-2-hydroxy-benzoicaci
5-Aminosalicyclic acid
5-aminosalicylic
5-amino-salicylicaci
Asacol
Asacolitin | [EINECS(EC#)]
201-919-1 | [Molecular Formula]
C7H7NO3 | [MDL Number]
MFCD00007877 | [Molecular Weight]
153.14 | [MOL File]
89-57-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Crystals | [Melting point ]
275-280 °C (dec.) (lit.) | [Boiling point ]
276.03°C (rough estimate) | [density ]
1.3585 (rough estimate) | [vapor pressure ]
0Pa at 25℃ | [refractive index ]
1.5500 (estimate) | [Fp ]
279-281°C | [storage temp. ]
2-8°C
| [solubility ]
Soluble in dimethyl sulfoxide. | [form ]
tablets
| [pka]
2.74, 5.84(at 25℃) | [color ]
off-white to gray
| [PH]
4.0-4.1 (0.8g/l, H2O, 20℃) | [PH Range]
Non-B uorescence (3.1) to light green B uorescence (4.4) | [Stability:]
Stable. Incompatible with acids, acid anhydrides, acid chlorides, chloroformates, strong oxidizing agents. | [Water Solubility ]
<0.1 g/100 mL at 21 ºC | [Decomposition ]
279-281 ºC | [Usage]
The active metabolite of Sulfasalazine. Anti-inflammatory (gastrointestinal) | [Detection Methods]
T,HPLC,NMR | [Merck ]
14,5904 | [BRN ]
2090421 | [BCS Class]
4 | [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℃ | [CAS DataBase Reference]
89-57-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Mesalamine(89-57-6) | [Storage Precautions]
Air sensitive;Store under nitrogen;Light sensitive | [EPA Substance Registry System]
89-57-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
2
| [RTECS ]
VO1400000
| [F ]
8-10-23 | [Autoignition Temperature]
280 °C | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29225000 | [Hazardous Substances Data]
89-57-6(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 2800 mg/kg LD50 dermal Rat > 5000 mg/kg |
| Hazard Information | Back Directory | [General Description]
Odorless white to pinkish crystals or purplish-tan powder. Aqueous solutions acidic (pH approximately 4.1 at 0.8 mg/L water) . | [Reactivity Profile]
5-AMINOSALICYLIC ACID(89-57-6) is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers. | [Air & Water Reactions]
Sensitive to moisture. Water insoluble. | [Fire Hazard]
Flash point data for this chemical are not available; however, 5-AMINOSALICYLIC ACID is probably combustible. | [Description]
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. | [Chemical Properties]
Off-White Crystals | [Originator]
Radcliffe Infirmary (United Kingdom) | [Uses]
anesthetic (local) | [Uses]
For the treatment of active ulcerative proctitis. | [Uses]
In manufacture of light-sensitive paper, azo and sulfur dyes. | [Uses]
peroxidase substrate | [Uses]
The active metabolite of Sulfasalazine (S699084). Anti-inflammatory (gastrointestinal). | [Application]
5-Aminosalicylic acid (5-ASA) 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. | [Definition]
ChEBI: A monohydroxybenzoic acid that is salicylic acid which is substituted by an amino group at the 5-position. | [Preparation]
Preparation by reduction of m-nitrobenzoic acid with Zn dust and HCl. | [Manufacturing Process]
Procedure A: To 5-nitrosalicylic acid potassium salt (55 g, 246 mmol) dissolved in water (200 mL) was added potassium hydroxide pellets to reach pH 11.5. To this solution 2 g of Raney nickel were added. The mixture was heated-up to reflux and hydrazine hydrate (40 mL, 80% in water, 64 mmol) was added dropwise during 3-4 hrs. The reflux was maintened until HPLC showed the disappearance of the starting material and the complete reduction of 5-nitrosalicylic acid (3-4 hrs). The hot mixture was filtered under nitrogen and the solution was collected. The solution was cooled to 40°C and the pH was adjusted to 2.3 by addition of 35% HCl aqueous solution. The precipitation of 5-aminosalicylic acid occurred. The solution was cooled at 0°C, and after standing at this temperature for 2 hr, the precipitate was filtered, washed with water, and dried at 60-70°C. 5-Aminosalicylic acid was obtained in 89% yield.
Procedure B: To 5-nitrosalicylic acid potassium salt (55 g, 246 mmol) dissolved in water (200 mL) was added potassium hydroxide pellets to reach pH 11.5. The solution was charged in a stainless steel autoclave and 2 g of Raney nickel are added. Hydrogen was introduced into the autoclave reaching a pressure of 8 atm. The mixture was heated-up to 100°C. The temperature was maintained until HPLC-test 5-aminosalicylic acid showed the disappearance of the starting material and the complete reduction of 5- aminosalicylic acid (6-8 hrs). Hydrogen was purged and replaced by nitrogen. The hot mixture was filtered under nitrogen, the filtrate was cooled to 40°C, and the pH was adjusted to 2.3 by addition of 35% HCl aqueous solution. The precipitation of the 5-aminosalicylic acid occurred. The solution was cooled at 0°C, and after standing at this temperature for 2 hr, the precipitate was filtered, washed with ion depleted water, and dried at 60-70°C. | [Brand name]
SALOFALK | [Therapeutic Function]
Antibacterial | [Flammability and Explosibility]
Nonflammable | [Biochem/physiol Actions]
5-Aminosalicylic acid (5-ASA) 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-ASA is an active component of sulfasalazine and also consists of the carbohydrate polymer, inulin. It might exhibit anti-oxidant activity to lessen tissue injury. 5-ASA 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-ASA stimulates the membranous expression of E-cadherin and boosts intercellular adhesion. | [Clinical Use]
Induction and maintenance of remission in ulcerative
colitis | [Safety Profile]
Poison by intraperitoneal route.Moderately toxic by ingestion. Human systemic effects byingestion: hypermotility, diarrhea, dermatitis, increasedbody temperature. When heated to decomposition it emitstoxic fumes of NOx. | [Drug interactions]
Potentially hazardous interactions with other drugs
None known | [Metabolism]
The absorbed part of mesalazine is almost completely
acetylated in the gut wall and in the liver to acetyl-5-
aminosalicylic acid.
The acetylated metabolite is excreted mainly in urine by
tubular secretion, with traces of the parent compound. | [storage]
4°C, protect from light, stored under nitrogen | [Purification Methods]
It crystallises as needles from H2O containing a little NaHSO3 to avoid aerial oxidation to the quinone-imine. The Me ester gives needles from *C6H6, m 96o, and the hydrazide has m 180-182o (from H2O). [Fallab et al. Helv Chim Acta 34 26 1951, Shavel J Amer Pharm Assoc 42 402 1953, Beilstein 14 IV 2058.] |
| Questions And Answer | Back Directory | [Indication]
It is used for the treatment of active ulcerative proctitis.
| [References]
- Martin F. Oral 5-aminosalicylic acid preparations in treatment of inflammatory bowel disease: an update. Dig Dis Sci 1987; 32 (12 Suppl.): 57S-63S
- Azad Khan AK, Piris J, Truelove SC. An experiment ot determine the active therapeutic moiety of sulphasalazine. Lancet 1979; II (8044): 892-5
- Schröder H, Price E, Evans DA. Acetylator phenotype and adverse events of sulphasalazine in healthy subjects. Gut 1972; 13 (4): 278-84
- Haagen Nielsen O, Bondesen S. Kinetics of 5-aminosalicylic acid after jejunal instillation in man. Br J Clin Pharmacol 1983; 16 (6): 738-40
- Ireland A, Jewell DP. Mechanism of action of 5-aminosalicylic acid and its derivatives. Clin Sci 1990; 78: 119-25
- Greenfield SM, Punchard NA, Teare JP, et al. Review article: the mode of action of the aminosalicylates in inflammatory bowel disease. Aliment Pharmacol Ther 1993; 7: 369-83
- Travis SPL, Jewell DP. Salicylates for ulcerative colitis – their mode of action. Pharmacol Ther 1994; 63: 135-61
- Schmidt C, Fels T, Baumeister B, et al. The effect of 5aminosalicylate and para-aminosalicylate on the synthesis of prostaglandin E2 and leukotriene B4 in isolated colonic mucosal cells. Curr Med Res Opin 1996; 13 (7): 417-25
- Capasso F, Tavares IA, BennettA. Release of platelet-activating factor (PAF) from human colon mucosa and its inhibition by 5-aminosalicylic acid. Drugs Exp Clin Res 1991; 17: 351-3
- Rachmilewitz D, Karmeli F, Schwartz LW, et al. Effect of aminophenols (5-ASA and 4-ASA) on colonic interleukin-1 generation. Gut 1992; 33: 929-32
- Di Paolo MC, Merrett MN, Crotty B, et al. 5-Aminosalicylic acid inhibits the impaired epithelial barrier function induced by gamma interferon. Gut 1996; 38: 115-9
- Vainio H, Morgan G. Non-steroidal anti-inflammatory drugs and the chemoprevention of gastrointestinal cancers. Scand J Gastroenterol 1998; 33: 785–9.
- Bus PJ, Nagtegaal ID, Verspaget HW, et al. Mesalazine-induced apoptosis of colorectal cancer: on the verge of a new chemopreventive era? Aliment Pharmacol Ther 1999; 13: 1397–402.
- Reinacher-Schick A, Seidensticker F, Petrasch S, et al. Mesalazine changes apoptosis and proliferation in normal mucosa of patients with sporadic polyps of the large bowel. Endoscopy 2000; 32: 245–54.
- Egan LJ, Mays DC, Huntoon MP, et al. Inhibition of interleukin-1-stimulated NF-jB RelA ⁄ p65 phosphorylation by mesalazine is accompanied by decreased transcriptional activity. J Biol Chem 1999; 274: 26448–53.
- Bondesen S, Hegnhoj J, Larsen F, et al. Pharmacokinetics of 5-aminosalicylic acid in man following administration of intravenous bolus and Per Os slow-release formulation. Dig Dis Sci 1991; 36: 1735-40
- Daneshmend TK, Hendrickse M, Salzmann M, et al. Does systemic absorption of 5-aminosalicylic acid from olsalazine (Dipentum®) and mesalazine (Asacol® and Pentasa®) differ significantly in ulcerative colitis?[abstract]. Gut 1994; 35 Suppl. 4: 233
- Staerk-Laursen L, Stokholm M, Bukhave K, et al. Disposition of 5-aminosalicylic acid by olsalazine and three mesalazine preparations in patients with ulcerative colitis: comparison of intraluminal colonic concentrations, serum values, and urinary excretion. Gut 1990; 31: 1271-6
- Christensen LA, Rasmussen SN, Hansen SH. Disposition of 5-aminosalicylic acid and N-acetyl-5-aminosalicylic acid in fetal and maternal body fluids during treatment with different 5-aminosalicylic acid preparations. Acta Obstet Gynecol Scand 1994; 74: 399-402
- Lauritsen K, Laursen LS, Rask-Madsen J. Clinical pharmacokinetics of drugs used in the treatment of gastrointestinal diseases (Part II). Clin Pharmacokinet 1990; 19: 94-125
- Rasmussen SN, Bondesen S, Hvidberg EF, et al. 5-Aminosalicylic acid in a slow-release prepararation: bioavailability, plasma level, and excretion in humans. Gastroenterolo 1982; 83: 1062-70
- Christensen LA, Fallingborg J, Abildgaard K, et al. Topical and systemic availability of 5-amino-salicylate: comparisons of three controlled release preparations in man. Aliment Pharmacol Ther 1990; 4: 523-33
- Christensen LA, Fallingborg J, Jacobsen BA, et al. Comparative bioavailability of 5-aminosalicylic acid from a controlled release preparation and an azo-bond preparation. Aliment Pharmacol Ther 1994; 8: 289-94
- Hanauer S, Schwartz J, RobinsonM, et al.Mesalamine capsules for the treatment of active ulcerative colitis: results of a controlled trial. Am J Gastroenterol 1993; 88: 1188-97
- Miner P, Hanauer S, Robinson M, et al. Safety and efficacy of controlled-release mesalamine for maintenance of remission in ulcerative colitis. Dig Dis Sci 1995; 40: 296-304
- Singleton JW, Hanauer SB, Gitnick GL, et al. Mesalamine capsules for the treatment of active Crohn’s disease: results of a 16-week trial. Pentasa Crohn’s Disease Study Group[see comments]. Gastroenterology 1993; 104: 1293-301
- Hanauer SB, Krawitt EL, Robinson M, et al. Long-term management of Crohn’s disease with mesalamine capsules (Pentasa ®). Am J Gastroenterol 1993; 88: 1343-51
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