Sulfaphenazole

Base Information

• Chemical Name: Sulfaphenazole
• CAS No.: 526-08-9
• Molecular Formula: C15H14 N4 O2 S
• Molecular Weight: 314.368
• Hs Code.: 2935009090
• European Community (EC) Number: 208-384-3
• NSC Number: 757859
• UNII: 0J8L4V3F81
• DSSTox Substance ID: DTXSID2044131
• Nikkaji Number: J2.062A
• Wikipedia: Sulfaphenazole
• Wikidata: Q6577293
• NCI Thesaurus Code: C66569
• Pharos Ligand ID: CYAJWRGN8KSA
• Metabolomics Workbench ID: 43697
• ChEMBL ID: CHEMBL1109
• Mol file: 526-08-9.mol

Synonyms:Phenylsulfapyrazole;Sulfaphenazole;Sulfaphenylpyrazol;Sulphaphenazole

Chemical Property of Sulfaphenazole

Chemical Property:

• Vapor Pressure: 8.34E-12mmHg at 25°C
• Melting Point: 179-183 °C
• Refractive Index: 1.6440 (estimate)
• Boiling Point: 541.9°Cat760mmHg
• PKA: pKa 5.71(H2O t = 25 I = 0.05) (Uncertain)
• Flash Point: 281.5°C
• PSA: 98.39000
• Density: 1.39g/cm³
• LogP: 3.99030
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 314.08374688
• Heavy Atom Count: 22
• Complexity: 451

Purity/Quality:

99% ^*data from raw suppliers

Trefoil Factor 2 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N2C(=CC=N2)NS(=O)(=O)C3=CC=C(C=C3)N
• Description: CYP2C9 is a major cytochrome P450 enzyme that is involved in the metabolic clearance of various therapeutic agents. Disruption of this enzyme’s activity can lead to adverse drug reactions. Sulfaphenazole is an inhibitor of CYP2C9 (Ki = 0.3 μM) that demonstrates at least 100-fold selectivity over other CYP450 isoforms (Kis = 63 and 29 μM for CYP2C8 and CYP2C18, respectively, and no activity at CYP1A1, CYP1A2, CYP3A4, CYP2C19). At 10 μM, sulfaphenazole has been shown to inhibit endothelium-derived hyperpolarizing factor synthase, a CYP450 isozyme in the porcine coronary artery homologous to CYP2C8/9 that generates reactive oxygen species in coronary endothelial cells and modulates vascular tone and homeostasis.
• Uses: Sulfaphenazole is used as an inhibitor for mammalian CYP2C9, an enzyme of the cytochrome P450 family allowing for pharmacological application. Sulfaphenazole can help protect against ischemia-reperfus ion, and resulting tissue damage by inhibition of CYP2C9. Sulfaphenazole has been used as a positive control to inhibit cytochrome P450 2C9 (cyp2c9) to quantify Rhodiola rosea inhibition. It has also been used as cytochrome P450 2C9 (cyp2c9) inhibitor in endothelial cells and microsomal preparations. Sulfaphenazole is used as an inhibitor for mammalian CYP2C9, an enzyme of the cytochrome P450 family allowing for pharmacological application.Sulfaphenazole can help protect against ischemia-reperfusion, and resulting tissue damage by inhibition of CYP2C9.

Technology Process of Sulfaphenazole

There total 5 articles about Sulfaphenazole 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: 98.0%

N4-Acetylsulfaphenazole (855-91-4) → sulfaphenazole (526-08-9)

Guidance literature:

With water; sodium hydroxide; for 2h; Reflux;

DOI:10.1016/j.bmcl.2021.127924

Reference yield:

p-acetylaminobenzenesulfonyl chloride (121-60-8) → sulfaphenazole (526-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 5 h / 95 °C / Inert atmosphere

2: water; sodium hydroxide / 2 h / Reflux

With water; sodium hydroxide; In pyridine;

DOI:10.1016/j.bmcl.2021.127924

Reference yield:

1-phenylpyrazol-5-amine (826-85-7) → sulfaphenazole (526-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 5 h / 95 °C / Inert atmosphere

2: water; sodium hydroxide / 2 h / Reflux

With water; sodium hydroxide; In pyridine;

DOI:10.1016/j.bmcl.2021.127924

upstream raw materials:

[4-(2-phenyl-2H-pyrazol-3-ylsulfamoyl)-phenyl]-carbamic acid ethyl ester

p-acetylaminobenzenesulfonyl chloride

N₄-Acetylsulfaphenazole

1-phenylpyrazol-5-amine

Downstream raw materials:

4-[(1H-Benzoimidazol-2-ylmethyl)-amino]-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide

4-[(5-Nitro-1H-benzoimidazol-2-ylmethyl)-amino]-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide

4-[2-Amino-4-(4-methoxy-phenyl)-thiazol-5-ylazo]-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide

4-amino-N-(2-o-tolyl-2H-pyrazol-3-yl)-benzenesulfonamide

Refernces

• 1、 -. "Process for formulating a synthetic drug for use in animal feed, and resulting formulation". . . Retrieved 2008/06/13.