Indication References
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5-Aminosalicylic acid

Indication References
Product Name
5-Aminosalicylic acid
CAS No.
89-57-6
Chemical Name
5-Aminosalicylic acid
Synonyms
MESALAZINE;MESALAMINE;5-ASA;5-AMINO-2-HYDROXYBENZOIC ACID;Asacol;rowasa;3-Carboxy-4-hydroxyaniline;Canasa;Pentasa;Mesalmine
CBNumber
CB1480481
Molecular Formula
C7H7NO3
Formula Weight
153.14
MOL File
89-57-6.mol
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5-Aminosalicylic acid Property

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)
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-B uorescence (3.1) to light green B uorescence (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℃
CAS DataBase Reference
89-57-6(CAS DataBase Reference)
NIST Chemistry Reference
Mesalamine(89-57-6)
EPA Substance Registry System
Benzoic acid, 5-amino-2-hydroxy- (89-57-6)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38-52/53
Safety Statements 
26-36-24/25-61-37/39
WGK Germany 
2
RTECS 
VO1400000
F 
8-10-23
Autoignition Temperature
280 °C
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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
BP1075
Product name
Mesalazine
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
125MG
Price
$257
Updated
2024/03/01
Sigma-Aldrich
Product number
1392705
Product name
Mesalamine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
8.20095
Product name
5-Amino-2-hydroxybenzoic acid
Purity
for synthesis
Packaging
250g
Price
$97.3
Updated
2022/05/15
Sigma-Aldrich
Product number
18858
Product name
5-Aminosalicylic acid
Purity
analytical standard
Packaging
100mg
Price
$55.2
Updated
2021/12/16
TCI Chemical
Product number
A0317
Product name
5-Aminosalicylic Acid
Purity
>98.0%(T)
Packaging
25g
Price
$27
Updated
2024/03/01
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5-Aminosalicylic acid Chemical Properties,Usage,Production

Indication

It is used for the treatment of active ulcerative proctitis.

References

  1. Martin F. Oral 5-aminosalicylic acid preparations in treatment of inflammatory bowel disease: an update. Dig Dis Sci 1987; 32 (12 Suppl.): 57S-63S
  2. Azad Khan AK, Piris J, Truelove SC. An experiment ot determine the active therapeutic moiety of sulphasalazine. Lancet 1979; II (8044): 892-5
  3. Schröder H, Price E, Evans DA. Acetylator phenotype and adverse events of sulphasalazine in healthy subjects. Gut 1972; 13 (4): 278-84
  4. Haagen Nielsen O, Bondesen S. Kinetics of 5-aminosalicylic acid after jejunal instillation in man. Br J Clin Pharmacol 1983; 16 (6): 738-40
  5. Ireland A, Jewell DP. Mechanism of action of 5-aminosalicylic acid and its derivatives. Clin Sci 1990; 78: 119-25
  6. 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
  7. Travis SPL, Jewell DP. Salicylates for ulcerative colitis – their mode of action. Pharmacol Ther 1994; 63: 135-61
  8. 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
  9. 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
  10. 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
  11. 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
  12. Vainio H, Morgan G. Non-steroidal anti-inflammatory drugs and the chemoprevention of gastrointestinal cancers. Scand J Gastroenterol 1998; 33: 785–9.
  13. 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.
  14. 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.
  15. 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.
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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
  24. 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
  25. 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
  26. 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
  27. 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

Description

5-Aminosalicylic acid (5-ASA), 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. 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.

Chemical Properties

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.

Originator

Radcliffe Infirmary (United Kingdom)

Uses

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.

Definition

ChEBI: 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 an aromatic amine, an amino acid, a member of phenols, a monocarboxylic acid and a monohydroxybenzoic acid. It is functionally related to a salicylic acid. It is a conjugate acid of a mesalaminate(1-).

Preparation

Preparation by reduction of m-nitrobenzoic acid with Zn dust and HCl.

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.

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

General Description

Odorless white to pinkish crystals or purplish-tan powder. Aqueous solutions acidic (pH approximately 4.1 at 0.8 mg/L water) .

Air & Water Reactions

Sensitive to moisture. Water insoluble.

Reactivity Profile

5-Aminosalicylic acid is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers.

Fire Hazard

Flash point data for 5-Aminosalicylic acid are not available; however, 5-Aminosalicylic acid is probably combustible.

Flammability and Explosibility

Non flammable

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.

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.

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.]

5-Aminosalicylic acid Preparation Products And Raw materials

Raw materials

ZINC Nitro Sodium dithionite Salicylic acid 5-Nitrosalicylic acid Water Methanesulfonyl chloride Tyramine Sodium carbonate

Preparation Products

Benzoic acid, 2-[[1-amino-7-[[4-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sulfo-2-naphthalenyl]azo]-2-methoxyphenyl]azo]-8-hydroxy-3,6-disulfo-2-naphthalenyl]azo]-5-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sul
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5-Aminosalicylic acid Suppliers

Americas 1 Belgium 7 Brazil 3 Canada 7 China 535 Cyprus 1 Denmark 1 Egypt 1 Europe 4 France 5 Germany 21 India 146 Indonesia 1 Italy 7 Japan 9 Malaysia 1 Nepal 1 Philippines 1 Poland 1 Russia 1 Slovakia 1 South Africa 1 South Korea 3 Spain 4 Sweden 1 Switzerland 5 The Netherlands 3 Ukraine 2 United Arab Emirates 1 United Kingdom 24 United States 77 Uruguay 1 Global 877
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Shanghai Yolne Chemical Co., Ltd.
Tel
021-62960152
Fax
021-52212593
Email
934678158@qq.com
Country
China
ProdList
9899
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55
Nanjing Dulai Biotechnology Co., Ltd.
Tel
025-84699383-8003 18013301590
Fax
025-84699383-8003
Email
njduly@126.com
Country
China
ProdList
971
Advantage
55
Chengdu AstaTech Trading Co., Ltd./AstaTech (Chengdu) Pharma. Co., Ltd.
Tel
+86-28-85122536 85324413
Fax
+86-28-85326443
Email
market@astatech.cn
Country
China
ProdList
8026
Advantage
55
Nanjing Sunlida Biological Technology Co., Ltd.
Tel
025-57798810
Fax
025-57019371
Email
sales@sunlidabio.com
Country
China
ProdList
3239
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55
TargetMol Chemicals Inc.
Tel
021-021-33632979 15002134094
Fax
021-33632979
Email
marketing@targetmol.com
Country
China
ProdList
7783
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58
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View Lastest Price from 5-Aminosalicylic acid manufacturers

Sinoway Industrial co., ltd.
Product
Mesalazine 89-57-6
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20tons
Release date
2024-05-31
Hebei Zhuanglai Chemical Trading Co Ltd
Product
5-Aminosalicylic Acid 89-57-6
Price
US $79.00-38.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-11-19
WUHAN FORTUNA CHEMICAL CO., LTD
Product
5-Aminosalicylic acid (Mesalazine) 89-57-6
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98.5%~101.5%; USP40
Supply Ability
15tons/month
Release date
2021-06-04

89-57-6, 5-Aminosalicylic acidRelated Search:

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