Selexipag

Base Information

• Chemical Name: Selexipag
• CAS No.: 475086-01-2
• Molecular Formula: C26H32N4O4S
• Molecular Weight: 496.62168
• European Community (EC) Number: 809-991-1
• UNII: 5EXC0E384L
• DSSTox Substance ID: DTXSID301027959
• Nikkaji Number: J2.120.977E
• Wikipedia: Selexipag
• Wikidata: Q15424759
• NCI Thesaurus Code: C152321
• RXCUI: 1729002
• Pharos Ligand ID: UQXJU3FH7KDL
• Metabolomics Workbench ID: 152574
• ChEMBL ID: CHEMBL238804
• Mol file: 475086-01-2.mol

Synonyms:2-(4-((5,6-diphenylpyrazin-2-yl)(isopropyl)amino)butoxy)-N-(methylsulfonyl)acetamide;ACT 293987;ACT-293987;ACT293987;NS-304;selexipag;Uptravi

Chemical Property of Selexipag

Chemical Property:

• PKA: 3.82±0.40(Predicted)
• PSA: 109.87000
• Density: 1.210±0.06 g/cm3(Predicted)
• LogP: 5.36970
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 496.21442669
• Heavy Atom Count: 35
• Complexity: 730

Purity/Quality:

HPLC>99% ^*data from raw suppliers

Selexipag ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Pulmonary Arterial Hypertension Agents
• Canonical SMILES: CC(C)N(CCCCOCC(=O)NS(=O)(=O)C)C1=CN=C(C(=N1)C2=CC=CC=C2)C3=CC=CC=C3
• Recent ClinicalTrials: A Study to Find Out if Selexipag is Effective and Safe in Patients With Chronic Thromboembolic Pulmonary Hypertension When the Disease is Inoperable or Persistent/Recurrent After Surgery and/or Interventional Treatment
• Recent EU Clinical Trials: A Multicenter, Single-arm, Open-label, Long-term Follow-up Safety Study of Selexipag in Participants who Participated in a Previous Selexipag Study.
• Recent NIPH Clinical Trials: Investigational Randomized Controlled Trial of Patients with Chronic Thromboembolic Pulmonary Hypertension treated with Riociguat vs Selexipag
• Description: Selexipag and its active metabolite, the corresponding carboxylic acid, are nonprostanoid prostaglandin I2 (PGI-2) receptor agonists. The N-methylsulfonamide within selexipag is hydrolyzed to the corresponding carboxylic acid in vivo by hepatic microsomes at a rate which provides a slow-release pharmacological effect. The compound was originally discovered by Nippon Shinyaki and later licensed to Actelion for development. The drug was approved in 2015 and first launched for the oral treatment of pulmonary arterial hypertension (PAH) in the U.S. in 2016 to delay disease progression and reduce the risk of hospitalization.
• Uses: Selexipag is an orally available, highly selective, long-acting prostacyclin (IP) receptor agonist prodrug. It is a potential drug for the treatment of various vascular disorders such as pulmonary arterial hypertension and arteriosclerosis obliterans.
• Clinical Use: Selexipag was approved by the United States FDA on December 22, 2015 for the treatment of pulmonary arterial hypertension (PAH) to delay disease progression and reduce risk of hospitalization.Selective IP receptor agonist:Treatment of pulmonary arterial hypertension.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: concentration possibly reduced by rifampicin - consider increasing selexipag dose Antiepileptics: concentration possibly reduced by carbamazepine, fosphenytoin and phenytoin - consider increasing selexipag dose. Clopidogrel: concentration of selexipag possibly increased - consider reducing dose of selexipag. Deferasirox: concentration of selexipag possibly increased - consider reducing dose of selexipag. Lipid-lowering drugs: concentration possibly increased by gemfibrozil - avoid. Teriflunomide: concentration of selexipag possibly increased - consider reducing dose of selexipag

Technology Process of Selexipag

There total 32 articles about Selexipag 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: 96.8%

MRE-269 (475085-57-5) + methanesulfonamide (3144-09-0) → Selexipag (475086-01-2)

Guidance literature:

MRE-269; With 1,1'-carbonyldiimidazole; In dichloromethane; for 1h; Reflux;

methanesulfonamide; In dichloromethane; at 20 - 30 ℃; for 0.166667h;

With triethylamine; In dichloromethane; for 5h; Reagent/catalyst;

Reference yield: 89.7%

4-[N-(5,6-diphenylpyrazine-2-yl)-N-isopropylamino]-1-butanol (475086-75-0) + 2-chloro-N-(methylsulfonyl)acetamide (202658-88-6) → Selexipag (475086-01-2)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 5 ℃; for 1h;

Reference yield: 88.9%

(5,6-diphenyl-pyrazin-2-yl)-isopropyl-amine + C7H14BrNO4S → Selexipag (475086-01-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 6h;

upstream raw materials:

MRE-269

methanesulfonamide

4-hydroxy-N-isopropylbutan-1-amine

4-[N-(5,6-diphenylpyrazine-2-yl)-N-isopropylamino]-1-butanol

Refernces

• 1、 -. "Synthesis method of diphenyl pyrazine derivative". Paragraph 0059-0063; 0064-0066; 0069-0070. . Retrieved 2021/06/13.
• 2、 -. "METHOD FOR PREPARING PROSTACYCLIN RECEPTOR AGONIST". Paragraph 0076-079. . Retrieved 2018/03/01.