Cariporide

Base Information

• Chemical Name: Cariporide
• CAS No.: 159138-80-4
• Molecular Formula: C12H17N3O3S
• Molecular Weight: 283.351
• UNII: 7E3392891K
• DSSTox Substance ID: DTXSID8047345
• Nikkaji Number: J812.746H
• Wikipedia: Cariporide
• Wikidata: Q5039665
• NCI Thesaurus Code: C76028
• Pharos Ligand ID: UTNGY3JBVPA6
• Metabolomics Workbench ID: 149794
• ChEMBL ID: CHEMBL436559
• Mol file: 159138-80-4.mol

Synonyms:4-isopropyl-3-(methylsulfonyl)benzoyl-guanidine methanesulfonate;cariporide;HOE 642;HOE-642;HOE642

Chemical Property of Cariporide

Chemical Property:

• Vapor Pressure: 7.62E-12mmHg at 25°C
• Melting Point: 90-94° (dec)
• Refractive Index: 1.601
• Boiling Point: 542.8 °C at 760 mmHg
• Flash Point: 282.1 °C
• PSA: 123.99000
• Density: 1.34 g/cm³
• LogP: 3.10850
• Storage Temp.: 2-8°C
• Solubility.: insoluble in H2O; ≥12.05 mg/mL in DMSO; ≥2.675 mg/mL in EtOH with gentle warming and ultrasonic
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 283.09906259
• Heavy Atom Count: 19
• Complexity: 461

Purity/Quality:

99% ^*data from raw suppliers

Cariporide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C=C(C=C1)C(=O)N=C(N)N)S(=O)(=O)C
• Uses: Reduction of death and nonfatal myocardial infarction in patients undergoing CABG surgery. Cariporide is an Na+/H+ exchange inhibitor that functions to improve cellular integrity following events of cardiac ischemia and reperfusion (most commonly seen in non-heart beating donor organs). Cariporide is also used to prevent heart attacks in high-risk ischemic patients.

Technology Process of Cariporide

There total 7 articles about Cariporide 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: 92.0%

guanidine nitrate (113-00-8) + 4-Isopropyl-3-methanesulfonyl-benzoic acid methyl ester (176107-23-6) → cariporide (159138-80-4)

Guidance literature:

In tetrahydrofuran; for 1.5h; Heating;

Reference yield:

3-Methylsulfonyl-4-i-propylbenzoyl Chloride (167764-63-8) + guanidine hydrochloride (50-01-1) → cariporide (159138-80-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 30 - 40 ℃; for 4h;

Reference yield:

2-Isopropyl-5-carboxybenzenesulfinic acid (159139-34-1) → cariporide (159138-80-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / water; N,N-dimethyl-formamide / 3 h / 60 °C

2: thionyl chloride / toluene / 1 h / Heating / reflux

3: sodium hydroxide / tetrahydrofuran; water / 4 h / 30 - 40 °C

With sodium hydroxide; thionyl chloride; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

guanidine nitrate

4-Isopropyl-3-methanesulfonyl-benzoic acid methyl ester

methyl 3-methylsulfonyl-4-bromobenzoate

3-Methylsulfonyl-4-i-propylbenzoyl Chloride

Downstream raw materials:

HOE₆₄₂

Refernces

• 1、 Weichert, Andreas,Faber, Sabine,Jansen, Hans W.,Scholz, Wolfgang,Lang, Hans J.. "Synthesis of the highly selective Na+/H+ exchange inhibitors cariporide mesilate and (3-methanesulfonyl-4-piperidino-benzoyl) guanidine methanesulfonate". . p. 1204 - 1207. Retrieved 2007/10/03.