Nifekalant hydrochloride

Base Information

• Chemical Name: Nifekalant hydrochloride
• CAS No.: 130656-51-8
• Molecular Formula: C19H28ClN5O5
• Molecular Weight: 441.915
• UNII: TPP5R0MDQS
• DSSTox Substance ID: DTXSID7048374
• Wikipedia: Nifekalant
• Wikidata: Q27290131
• NCI Thesaurus Code: C75132
• ChEMBL ID: CHEMBL553090
• Mol file: 130656-51-8.mol

Synonyms:1,3-dimethyl-6-((2-(N-(2-hydroxyethyl)-3-(4-nitrophenyl)propylamino)ethylamino)-2,4(1H),3H)-pyrimidinedione hydrochloride;MS 551;MS-551;nifekalant;nifekalant hydrochloride

Chemical Property of Nifekalant hydrochloride

Chemical Property:

• Melting Point: 172-174°
• Boiling Point: 597.9 °C at 760 mmHg
• PKA: 7.05(at 25℃)
• Flash Point: 315.4 °C
• PSA: 125.32000
• LogP: 1.72940
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated), Water (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 441.1778967
• Heavy Atom Count: 30
• Complexity: 613

Purity/Quality:

98%,99%, ^*data from raw suppliers

NifekalantHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=CC(=O)N(C1=O)C)NCCN(CCCC2=CC=C(C=C2)[N+](=O)[O-])CCO.Cl
• Recent ClinicalTrials: Nifekalant Versus Amiodarone in New-Onset Atrial Fibrillation After Cardiac Surgery
• Recent NIPH Clinical Trials: The Randomized Controlled Trial Evaluating Utility of Catheter Ablation Us ing ExTRa mapping for Atrial Fibrillation
• Description: Nifekalant is a novel and pure class III anti-arrhythmic agent introduced in Japan as Shinbit injection for the treatment of serious ventricular arrhythmias. It can be synthesized in 3 steps with a final assembly of two ethanolamine blocks. Nifekalant is a non-selective blocker of myocardial repolarizing potassium currents and is completely devoid of any β-adrenergic blocking effect . In hearts from different species, Nifekalant significantly prolonged action potential duration, atrial and ventricular refractory periods in in situ and in isolation studies. In intact animals, hemodynamic parameters were not affected by doses up to 1 mg/kg. The specific characteristics of its voltage- and timedependent K+ current blockade might differentiate Nifekalant from other class III agents currently in use. Nifekalant is a class III antiarrhythmic agent that has been shown to be beneficial to initial resuscitation after cardiac arrest in clinical trials. It blocks the rapidly activating delayed rectifier potassium channel (IKr; IC50 = 10 μM). Nifekalant is also inhibits the human multidrug and toxin extrusion (MATE) transporter 1 (MATE1; IC50 = 6.5 μM).
• Uses: Nifekalant Hydrochloride is a class III antiarrhythmic agent. Nifekalant Hydrochloride is used in the treatment of patients with extensive anterior infarction and severe ventricular dysfunction.

Technology Process of Nifekalant hydrochloride

There total 5 articles about Nifekalant hydrochloride 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: 87.6%

1,3-dimethyl-6-[2-(N-[2-hydroxyethyl]-3-[4-nitrophenyl]propylamino)ethylamino]-2,4(1H,3H)-pyrimidinedione (130636-43-0) → Shinbit (130656-51-8)

Guidance literature:

With hydrogenchloride; In ethanol; at 4 - 50 ℃; for 24h;

Reference yield:

3-(4-nitrophenyl)-1-propanol (20716-25-0) → Shinbit (130656-51-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / 2 h / 0 °C

2.1: sodium hydroxide / ethanol / 1 h / 50 - 60 °C

2.2: 1 h / 80 °C

3.1: hydrogenchloride / ethanol / 24 h / 4 - 50 °C

With pyridine; hydrogenchloride; sodium hydroxide; In ethanol;

Reference yield:

6-(2-hydroxyethylamino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dion (5770-44-5) → Shinbit (130656-51-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 2 h / 0 °C

2.1: sodium hydroxide / ethanol / 1 h / 50 - 60 °C

2.2: 1 h / 80 °C

3.1: sodium hydroxide / ethanol / 1 h / 50 - 60 °C

3.2: 1 h / 80 °C

4.1: hydrogenchloride / ethanol / 24 h / 4 - 50 °C

With pyridine; hydrogenchloride; sodium hydroxide; In ethanol;

upstream raw materials:

3-(4-nitrophenyl)-1-propanol

1,3-dimethyl-6-[2-(N-[2-hydroxyethyl]-3-[4-nitrophenyl]propylamino)ethylamino]-2,4(1H,3H)-pyrimidinedione

6-(2-hydroxyethylamino)-1,3-dimethylpyrimidine-2,4(1H,3H)-dion

6-Amino-1,3-dimethylbarbituric acid

Refernces