Balsalazide

Base Information

• Chemical Name: Balsalazide
• CAS No.: 80573-04-2
• Molecular Formula: C₁₇H₁₅N₃O₆
• Molecular Weight: 357.323
• Mol file: 80573-04-2.mol

Synonyms:Colazide;Benzoic acid,5-[(1E)-[4-[[(2-carboxyethyl)amino]carbonyl]phenyl]azo]-2-hydroxy- (9CI);Benzoic acid, 5-[[4-[[(2-carboxyethyl)amino]carbonyl]phenyl]azo]-2-hydroxy-,(E)-;Balsalazida;Balsalazido;Balsalazidum;

Chemical Property of Balsalazide

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 0Pa at 20℃
• Melting Point: 254-255 °C
• Refractive Index: 1.649
• Boiling Point: 729.6±60.0 °C(Predicted)
• PKA: 2.97±0.10(Predicted)
• PSA: 148.65000
• Density: 1.44 g/cm³
• LogP: 3.10120
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Balsalazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Colazide was launched in the UK for mild to moderate acute attacks of ulcerative colitis. It can be prepared by diazotization of 3-(4-aminobenzoylamino) propionic acid followed by condensation with salicylic acid. Colazide, an analogue of sulfasalazine, was found to be non-toxic and non-mutagenic in the Ames test. Once ingested the molecule releases a non-toxic fragment, 4-aminobenzoyl-β-alanine (poorly absorbed - 75% excretion in stool), and the active component 5- aminosalicylic acid (Mesalazine). The exact mechanism of action is not clearly understood but it is cytoprotective and has antiinflammatory properties. Other biological effects have been observed and include the following: (a) granulocyte activation is blocked, (b) there is a reduction in myeloperoxidase activity, and (c) a reduction in the release of arachidonic acid with a concomitant decrease in prostaglandin and leucotriene (as indicated by the lack of production of LTB4) production. It can behave as a reactive oxygen species (ROS) scavenger, inhibit PAF formation, reduce IL-1 production, and antagonize TNF and NK cells. While comparable in efficacy to sulfasalazine, Colazide removes the possibility of sulfasalazine side-effects, such as, agranulocytosis, hepatotoxicity and male infertility. Balsalazide is a prodrug form of 5-aminosalicylic acid (5-ASA; ). It is cleaved by bacterial azoreductases in the intestinal lumen to release 5-ASA. Balsalazide (600 mg/kg per day) decreases IL-2 levels and increases IL-6 levels in the serum and colonic mucosa membrane, as well as decreases micro- and macroscopic colonic damage, in a rat model of colitis induced by 2,4-dinitrochlorobenzene (DNCB). Formulations containing balsalazide have been used in the treatment of ulcerative colitis.
• Uses: An analogue of Sulfasalazine, A prodrug of 5-Aminosalicylic Acid An analogue of Sulfasalazine (S699084). A prodrug of 5-aminosalicylic acid where carrier molecule is 4-aminobenzoyl-β-alanine. Anti-inflammatory (gastrointestinal). Balsalazide-d4 is an isotopically labelled analog of Balsalazide (B116300), which is an analogue of Sulfasalazine (S699084). A prodrug of 5-aminosalicylic acid where carrier molecule is 4-aminobenzoyl-β-alanine. Anti-inflammatory (gastrointestinal).
• Therapeutic Function: Antiinflammatory
• Clinical Use: Treatment and maintenance of remission, in mild to moderate ulcerative colitis
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Balsalazide

There total 6 articles about Balsalazide 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: 95.0%

N-(4-aminobenzoyl)-B-alanine (7377-08-4) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → balsalazide (80573-04-2)

Guidance literature:

N-(4-aminobenzoyl)-B-alanine; With hydrogenchloride; sodium nitrite; In water; at 0 - 5 ℃; for 1h;

salicylic acid; With sodium carbonate; sodium hydroxide; In water; at 0 - 5 ℃; for 1h;

DOI:10.1080/00397910903221068

Reference yield: 67.0%

4-((2-carboxyethyl)carbamoyl)benzenediazonium chloride + salicylic acid (69-72-7,25496-36-0,8052-31-1) → balsalazide (80573-04-2)

Guidance literature:

With sodium carbonate; sodium hydroxide; In water; at 0 ℃; for 3h; pH=10; Reagent/catalyst; pH-value; Temperature;

DOI:10.1002/chem.201605359

Reference yield:

4-nitro-benzoyl chloride (122-04-3) → balsalazide (80573-04-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide / 2.5 h / 0 - 20 °C

2: hydrogen; palladium 10% on activated carbon / methanol / 3 h / 20 °C / 750.08 Torr / Inert atmosphere

3: sodium nitrite; nitric acid; hydrogenchloride / water / 1 h / 20 °C

4: sodium carbonate; sodium hydroxide / water / 3 h / 0 °C / pH 10

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; nitric acid; sodium carbonate; sodium hydroxide; sodium nitrite; In methanol; water;

DOI:10.1002/chem.201605359

upstream raw materials:

N-(4-aminobenzoyl)-B-alanine

salicylic acid

N-(4-nitrobenzoyl)-beta-alanine

4-nitro-benzoyl chloride

Refernces

• 1、 -. "A synthetic balsalazide sodium intermediates (by machine translation)". Paragraph 0013. . Retrieved 2019/01/07.
• 2、 Khan, Md. Umar,Baseer,Kumar, S. Ranjith,Saravanakumar,Prasannanjali,Gupta, P. Badarinadh,Kaushik, Vipin K.,Handa, Vijay K.,Islam, Aminul. "Synthesis and characterization of metabolites and potential impurities of balsalazide disodium, an anti-inflammatory drug". scheme or table. p. 2241 - 2253. Retrieved 2010/10/02.