Sitaxentan

Base Information

• Chemical Name: Sitaxentan
• CAS No.: 184036-34-8
• Deprecated CAS: 210421-64-0
• Molecular Formula: C₁₈H₁₅ClN₂O₆S₂
• Molecular Weight: 454.912
• UNII: J9QH779MEM
• DSSTox Substance ID: DTXSID0057673
• Nikkaji Number: J851.117I
• Wikipedia: Sitaxentan
• Wikidata: Q905664
• NCI Thesaurus Code: C73038
• Pharos Ligand ID: 8N9YNVQH31CH
• Metabolomics Workbench ID: 43666
• ChEMBL ID: CHEMBL282724
• Mol file: 184036-34-8.mol

Synonyms:N-(4-chloro-3-methyl-5-isoxazolyl)-2-((4,5-(methylenedioxy)-O-toly)acetyl)-3-thiophenesulfonamide;N-(4-chloro-3-methyl-5-isoxazolyl)-2-(3,4-(methylenedioxy)-6-methyl)phenylacetyl-3-thiophenesulfonamide;sitaxsentan;TBC 11251;TBC-11251;TBC11251

Chemical Property of Sitaxentan

Chemical Property:

• Vapor Pressure: 2.25E-14mmHg at 25°C
• Melting Point: 42-45°
• Refractive Index: 1.687
• Boiling Point: 663.9 °C at 760 mmHg
• PKA: 4.96±0.10(Predicted)
• Flash Point: 355.3 °C
• PSA: 144.35000
• Density: 1.558 g/cm³
• LogP: 5.11500
• Storage Temp.: 2-8°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 454.0060062
• Heavy Atom Count: 29
• Complexity: 720

Purity/Quality:

99%+, ^*data from raw suppliers

N-(4-Chloro-3-methylisoxazol-5-yl)-2-(2-(6-methylbenzo-[d]-[1,3]dioxol-5-yl)acetyl)thiophene-3-sulfonamide sodium salt95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1CC(=O)C3=C(C=CS3)S(=O)(=O)NC4=C(C(=NO4)C)Cl)OCO2
• Recent ClinicalTrials: Confirming The Sitaxsentan Dose In Patients Undergoing Heart Surgery
• Recent EU Clinical Trials: A PHASE 3, MULTI-CENTER, OPEN LABEL STUDY TO EVALUATE THE LONG-TERM SAFETY OF MONOTHERAPY SITAXSENTAN SODIUM AND COMBINATION THERAPY WITH SITAXSENTAN SODIUM AND SILDENAFIL CITRATE IN SUBJECTS WITH PULMONARY ARTERIAL HYPERTENSION
• Recent NIPH Clinical Trials: A 12 Week Safety And Efficacy Study Of Sitaxentan Sodium In Japanese Pulmonary Arterial Hypertension Patients
• Description: Sitaxsentan is a selective endothelin-A (ETA) receptor antagonist launched for the treatment of patients with pulmonary arterial hypertension (PAH), to improve exercise capacity. It is the second ET receptor antagonist to be marketed for this indication behind bosentan. PAH encompasses a heterogeneous group of disorders characterized by inappropriate overactivation of the endothelin system and is characterized by a progressive increase in pulmonary vascular resistance resulting from vascular remodeling, vasoconstriction, and cellular proliferation. Endothelin-1 (ET-1), a potent vasoconstrictor and smooth muscle mitogen, is a key contributor to the acceleration of the disease, and its effects are mediated through activation of ETA and ETB receptors. ETA receptors are found primarily on smooth muscle cells and, when activated, induce vasoconstriction and cellular proliferation. ETB receptors are expressed in both pulmonary vascular endothelial cells and smooth muscle cells, and their activation is associated with the renal and pulmonary clearance of ET.

Technology Process of Sitaxentan

There total 11 articles about Sitaxentan 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: 71.0%

(3,4-methylenedioxy)-6-methylbenzyl chloride (117661-72-0) → sitaxentan (184036-34-8,210421-64-0)

Guidance literature:

Reference yield: 71.0%

(3,4-methylenedioxy)-6-methylbenzyl chloride (117661-72-0) + 3{[(4-chloro-3-methyl-5-isoxazolyl)amino]sulfonyl}-2-thiophenecarboxylic acid (184040-74-2) → sitaxentan (184036-34-8,210421-64-0)

Guidance literature:

Reference yield:

C9H9ClMgO2 (1008726-80-4) + N-(4-chloro-3-methyl-5-isoxazolyl)-2-(N-methyl-N'-methoxy)aminocarbonyl-3-thiophenesulfonamide (210421-71-9) → sitaxentan (184036-34-8,210421-64-0)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 3h; Yield given;

DOI:10.1021/jm9700068

upstream raw materials:

C₉H₉ClMgO₂

N-(4-chloro-3-methyl-5-isoxazolyl)-2-(N-methyl-N'-methoxy)aminocarbonyl-3-thiophenesulfonamide

C₉H₅ClN₂O₄S₂

(3,4-methylenedioxy)-6-methylbenzyl chloride

Refernces

• 1、 -. "SUBSTITUTED THIOPHENES". Page/Page column 66. . Retrieved 2008/12/04.
• 2、 -. "PROCESSES FOR THE PREPARATION OF 4-CHLORO-3-METHYL-5-(2-(2-(6-METHYLBENZO[D][1,3]DIOXOL-5-YL)ACETYL)-3-THIENYLSULFONAMIDO) ISOXAZOLE". Page/Page column 12. . Retrieved 2008/06/13.