Sulfasalazine

Base Information

• Chemical Name: Sulfasalazine
• CAS No.: 599-79-1
• Molecular Formula: C18H14N4O5S
• Molecular Weight: 398.399
• Hs Code.: DERIVATION
• European Community (EC) Number: 209-974-3
• NSC Number: 757330,667219,203730
• UNII: 3XC8GUZ6CB
• DSSTox Substance ID: DTXSID0021256
• Nikkaji Number: J2.073G
• Wikipedia: Sulfasalazine
• Wikidata: Q420035,Q27166356,Q63398427
• NCI Thesaurus Code: C29469
• RXCUI: 9524
• Pharos Ligand ID: C2DRLL67G78H
• Metabolomics Workbench ID: 50025
• ChEMBL ID: CHEMBL421,CHEMBL242373,CHEMBL1206016,CHEMBL100848
• Mol file: 599-79-1.mol

Synonyms:Asulfidine;Azulfadine;Azulfidine;Azulfidine EN;Colo Pleon;Colo-Pleon;Pleon;Pyralin EN;ratio Sulfasalazine;ratio-Sulfasalazine;Salazopyrin;Salazosulfapyridine;Salicylazosulfapyridine;Sulfasalazin Heyl;Sulfasalazin medac;Sulfasalazin-Heyl;Sulfasalazine;Sulfasalazine FNA;Sulphasalazine;Ucine;Ulcol

Chemical Property of Sulfasalazine

Chemical Property:

• Appearance/Colour: brownish-yellow crystals
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 260-265 °C (dec.)(lit.)
• Refractive Index: 1.691
• Boiling Point: 689.347 °C at 760 mmHg
• PKA: pKa 0.6(H2O t = 20 I < 0.001) (Uncertain);2.4(H2O t = 20 I < 0.001) (Uncertain);9.7(H2O t = 20 I < 0.001) (Uncertain);11.8(H2O t = 20 I < 0.001) (Uncertain)
• Flash Point: 370.704 °C
• PSA: 149.69000
• Density: 1.488 g/cm³
• LogP: 4.85540
• Storage Temp.: Refrigerator
• Solubility.: NH4OH 1 M: 50 mg/mL, clear, red
• Water Solubility.: <0.1 g/100 mL at 25℃
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 398.06849073
• Heavy Atom Count: 28
• Complexity: 657

Purity/Quality:

99% ^*data from raw suppliers

Sulfasalazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-29/56-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N=NC3=CC(=C(C=C3)O)C(=O)O
• Recent ClinicalTrials: Sulfasalazine in Decreasing Opioids Requirements in Breast Cancer Patients
• Recent EU Clinical Trials: A prospective, randomized, controlled, open label, assessor-blinded, parallel-group Phase III clinical trial to evaluate the impact of tapering systemic immunosuppressive therapy in a treat-to-target approach on maintaining minimal disease activity in adult subjects with psoriatic arthritis
• Recent NIPH Clinical Trials: Exploratory study of the efficacy and safety of salazosulfapyridine for immune checkpoint inhibitor related colitis
• Description: Sulfasalazine (brand name Azulfidine in the U.S., Salazopyrin and Sulazine in Europe and Hong Kong) was developed in the 1950s specifically to treat rheumatoid arthritis. It was believed at the time that bacterial infections were the cause of rheumatoid arthritis. Sulfasalazine is a sulfa drug, (a derivative of mesalazine) and is formed by combining sulfa pyridine and salicylate with an azo bond. It may be abbreviated SSZ.
• Uses: Anti-inflammatory (gastrointestinal). Has been used in granulomatous colitis. anticolitis and Crohn's disease Sulfasalazine is an anti-inflammatory (gastrointestinal). Sulfasalazine has been used in granulomatous colitis. Sulfasalazine is a prodrug of the anti-inflammatory agent 5-aminosalicylic acid that is covalently linked to the antibiotic sulfapyridine by an azo bond. This bond is rapidly cleaved by bacteria in the terminal ileum and colon, thus releasing the active anti-inflammatory component. It has long been used in treatment of inflammatory bowel disease and rheumatoid arthritis because of its ability to induce T lymphocyte apoptosis, modulate inflammatory mediators from both cyclooxygenase/5-lipoxygenase pathways and NF-κB signaling pathways, attenuate transcription of proinflammatory cytokines, and activate PPARγ.[Cayman Chemical] An inhibitor of of GSH-H-transferase and NF-kB activation and an apoptosis inducer
• Indications: Sulfasalazine is used in the treatment of inflammatory bowel disease, including ulcerative colitis and Crohn's disease. It is also indicated for use in rheumatoid arthritis and used in other types of inflammatory arthritis (e.g. psoriatic arthritis) where it has a beneficial effect. It is often well tolerated compared to other DMARDS. In clinical trials for the treatment of chronic alcoholics, sulfasalazine has been found to reverse the scarring associated with cirrhosis of the liver . Cells called myofibroblasts, which contribute to scar tissue in a diseased liver, also appear to secrete proteins that prevent the breakdown of the scar tissue. Sulfasalazine appears to retard this secretion. Sulfasalazine (Azulfidine) is approved for the treatment of rheumatoid arthritis and ulcerative colitis. It is also used to treat ankylosing spondylitis and Crohn’s disease. Comparisons of sulfasalazine with other DMARDs suggest that it is more effective than hydroxychloroquine, azathioprine, and oral gold compounds. It is at least as effective as intramuscular gold and penicillamine. It has a greater degree of toxicity than hydroxychloroquine but less than gold compounds and penicillamine. After 5 years, approximately 75% of patients have discontinued sulfasalazine therapy, primarily because of a lack of efficacy as opposed to intolerable side effects. Sulfasalazine (Azulfidine) was first introduced in 1940 as a treatment for rheumatoid arthritis. It was found that a number of patients with coexistent inflammatory bowel disease showed improvement of their GI symptoms, and the drug has subsequently been used for the treatment of patients with inflammatory bowel disease.
• Clinical Use: Sulfasalazine (Azulfidine) was first introduced in 1940 as a treatment for rheumatoid arthritis. Sulfasalazine (2-hydroxy-5[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]benzoic acid or 5-[p-(2-pyridylsulfamoyl)phenylazo]salicylic acid) is a brownish yellow, odorlesspowder, slightly soluble in alcohol but practically insolublein water, ether, and benzene.Sulfasalazine is broken down in the body to m-aminosalicylicacid and sulfapyridine. The drug is excreted throughthe kidneys and is detectable colorimetrically in the urine,producing an orange-yellow color when the urine is alkalineand no color when the urine is acid.
• Drug interactions: Potentially hazardous interactions with other drugs Ciclosporin: may reduce ciclosporin levels.

Technology Process of Sulfasalazine

There total 9 articles about Sulfasalazine 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: 95.4%

sulphapyridine (144-83-2) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → sulfosalazine (599-79-1)

Guidance literature:

sulphapyridine; With hydrogenchloride; sodium nitrite; In water; at 2 ℃; for 0.333333h;

salicylic acid; With sodium hydroxide; In water; at 7 ℃; for 1.5h; Temperature; Concentration;

Reference yield: 94.9%

4-(Pyridin-2-ylsulfamoyl)-benzenediazonium; chloride + salicylic acid (69-72-7,25496-36-0,8052-31-1) → sulfosalazine (599-79-1)

Guidance literature:

With sodium hydroxide; at 7 ℃; for 1.5h; pH=10; pH-value; Temperature;

Reference yield: 94.2%

sodium salicylate (54-21-7) + C11H9ClN4O2S → sulfosalazine (599-79-1)

Guidance literature:

sodium salicylate; C₁₁H₉ClN₄O₂S; In water; at -30 ℃; for 0.0138889h;

With hydrogenchloride; In water; Temperature;

upstream raw materials:

sulphapyridine

salicylic acid

2-aminopyridine

p-acetylaminobenzenesulfonyl chloride

Downstream raw materials:

N-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy-5-({[(4-pyridin-2-yl)sulfamoyl]phenyl}diazenyl)benzamide

5-Aminosalicylic Acid

sulphapyridine

Refernces

• 1、 -. "Preparation method of salazosulfapyridine". Paragraph 0016. . Retrieved 2020/07/13.
• 2、 -. "A method for preparing liu Danhuang pyridine (by machine translation)". Paragraph 0049; 0050; 0051; 0052; 0053. . Retrieved 2016/10/07.