Sulfinpyrazone

Base Information

• Chemical Name: Sulfinpyrazone
• CAS No.: 57-96-5
• Molecular Formula: C23H20N2O3S
• Molecular Weight: 404.489
• Hs Code.: 2933194350
• European Community (EC) Number: 200-357-4
• NSC Number: 757332,75925
• UNII: V6OFU47K3W
• DSSTox Substance ID: DTXSID0023618
• Nikkaji Number: J1.384F
• Wikipedia: Sulfinpyrazone
• Wikidata: Q3790542
• NCI Thesaurus Code: C47739
• Pharos Ligand ID: H1KWLARWYZ5V
• Metabolomics Workbench ID: 43360
• ChEMBL ID: CHEMBL832
• Mol file: 57-96-5.mol

Synonyms:Anturan;Anturane;Apo Sulfinpyrazone;Apo-Sulfinpyrazone;Nu Sulfinpyrazone;Nu-Sulfinpyrazone;Sulfinpyrazone;Sulfoxyphenylpyrazolidin;Sulphinpyrazone

Chemical Property of Sulfinpyrazone

Chemical Property:

• Vapor Pressure: 6.2E-14mmHg at 25°C
• Melting Point: >300°C(lit.)
• Refractive Index: 1.716
• Boiling Point: 590.8 °C at 760 mmHg
• PKA: pKa 2.8(H2O t = RT I undefined) (Uncertain)
• Flash Point: 311.1 °C
• PSA: 76.90000
• Density: 1.39 g/cm³
• LogP: 4.79120
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Very slightly soluble in water, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.
• Water Solubility.: 2.601g/L(22 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 404.11946368
• Heavy Atom Count: 29
• Complexity: 571

Purity/Quality:

99% ^*data from raw suppliers

Sulfinpyrazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C(=O)C(C(=O)N2C3=CC=CC=C3)CCS(=O)C4=CC=CC=C4
• Description: Sulfinpyrazone is soluble in alkaline solutions. Its synthesis is similar to that of phenylbutazone (Fig. 36.33). It produces its uricosuric effect in a manner similar to that of probenecid. A dose of 35 mg produces a uricosuric effect equivalent to that produced by 100 mg of probenecid, whereas 400 mg/day of sulfinpyrazone produces an effect comparable to that obtained with doses of 1.5 to 2 g of probenecid. It also possesses, not surprisingly, some of the properties of phenylbutazone. It is an inhibitor of human platelet prostaglandin synthesis at the cyclooxygenase step, resulting in a decrease in platelet release and a reduction in platelet aggregation. This antiplatelet effect suggests a role for sulfinpyrazone in reducing the incidence of sudden death, which can occur in the first year following a myocardial infarction; however, it lacks the analgetic and anti-inflammatory effects of phenylbutazone. Sulfinpyrazone is a uricosuric agent that competitively inhibits uric acid reabsorption in kidney proximal tubules, which is a key mechanism targeted in the treatment of gout. It can also inhibit degranulation of platelets, reducing the release of ADP and thromboxane and diminishing platelet aggregation.
• Uses: Sulfinpyrazone is used upon exactly the same indications as phenylbutazone. Sulfinpyrazone is used in the treatment of gout acting as a uricosuric medication. As an anti-inflammatory and uricosuric agent, its side effects were severe enough to preclude its continuous use in the treatment of chronic gout. Evaluation of several chemical congeners indicated that the phenylthioethyl analog of phenylbutazone had promising anti-inflammatory and uricosuric activity. A metabolite, the sulfoxide pyrazone, exhibited enhanced uricosuric activity. Interestingly, the corresponding sulfone does not appear to be a metabolite. Sulfinpyrazone lacks the clinically striking anti-inflammatory and analgesic properties of phenylbutazone.
• Indications: Sulfinpyrazone (Anturane), another uricosuric agent, is chemically related to the antiinflammatory and uricosuric compound phenylbutazone. However, it lacks the antiinflammatory, analgesic, and sodium-retaining properties of phenylbutazone and possesses a number of undesirable side effects that limit its therapeutic usefulness.
• Therapeutic Function: Antiarthritic (uricosuric)
• Clinical Use: Sulfinpyrazone is a structural derivative of the anti-inflammatory drug phenylbutazone. Unlike phenylbutazone, however, sulfinpyrazone does not have significant anti-inflammatory activity. It does have potent uricosuric effects and frequently is used in the treatment of gout.
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: increased risk of bleeding with apixaban; enhances anticoagulant effect of coumarins; possibly increased risk of bleeding with dabigatran. Antidiabetics: enhances effect of sulphonylureas. Antiepileptics: increases concentration of fosphenytoin and phenytoin. Ciclosporin: may reduce ciclosporin levels.

Technology Process of Sulfinpyrazone

There total 4 articles about Sulfinpyrazone 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: 60.0%

caro's acid (7722-86-3) + 4-[2-(phenylthio)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione (3736-92-3) → 4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione (57-96-5,159000-48-3,159000-47-2)

Guidance literature:

With sodium hydrogencarbonate; sodium hydrogensulfite; In water; acetic acid; ethyl acetate; toluene;

Reference yield: 58.0%

2-(2-Benzenesulfinyl-ethyl)-malonic acid diethyl ester (81580-51-0) + diphenyl hydrazine (122-66-7) → 4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione (57-96-5,159000-48-3,159000-47-2)

Guidance literature:

With sodium ethanolate; In ethanol; for 24h; Reflux;

DOI:10.1039/d1gc03440e

Reference yield:

→ 4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione (57-96-5,159000-48-3,159000-47-2)

Guidance literature:

DOI:10.1002/hlca.19610440129

upstream raw materials:

caro's acid

4-[2-(phenylthio)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

2-(2-Benzenesulfinyl-ethyl)-malonic acid diethyl ester

diphenyl hydrazine

Downstream raw materials:

Ethyltartronic dianilide

2-(Phenylthio)ethyltartronic dianilide

2-(Phenylsulfinyl)ethyltartronic dianilide

Azobenzene

Refernces

• 1、 -. "Contraceptive method". . . Retrieved 2008/06/13.
• 2、 -. "Selective oxidation of 1,2-diphenyl-4-(2-phenylthio)ethyl)-3,5-pyrazolidinedione to the sulfinyl compound". . . Retrieved 2008/06/13.