Dantrolene sodium

Base Information

• Chemical Name: Dantrolene sodium
• CAS No.: 14663-23-1
• Molecular Formula: C14H9N4O5Na
• Molecular Weight: 336.239
• Hs Code.: 2934999090
• European Community (EC) Number: 238-706-8,829-303-3
• UNII: 28F0G1E0VF
• NCI Thesaurus Code: C61698
• RXCUI: 3106
• ChEMBL ID: CHEMBL928
• Mol file: 14663-23-1.mol

Synonyms:Dantrium;Dantrolene;Dantrolene Sodium;Sodium, Dantrolene

Chemical Property of Dantrolene sodium

Chemical Property:

• Appearance/Colour: COA
• Boiling Point: 85°C 4mm
• Flash Point: 283.1oC
• PSA: 127.05000
• LogP: 1.71410
• Storage Temp.: Store at RT
• Solubility.: Soluble in DMSO (up to 3 mg/ml)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 336.04706368
• Heavy Atom Count: 24
• Complexity: 536

Purity/Quality:

98.0%～102.0% ^*data from raw suppliers

Dantrolene, sodium salt ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(=NC(=O)N1N=CC2=CC=C(O2)C3=CC=C(C=C3)[N+](=O)[O-])[O-].[Na+]
• Isomeric SMILES: C1C(=NC(=O)N1/N=C/C2=CC=C(O2)C3=CC=C(C=C3)[N+](=O)[O-])[O-].[Na+]
• Recent ClinicalTrials: A Clinical Trial of Dantrolene Sodium in Pediatric and Adult Patients With Wolfram Syndrome
• Recent EU Clinical Trials: Dantrolene in catecholaminiergic polymorphic ventricular tachycardia
• Description: Dantrolene is an inhibitor of calcium release from the sarcoplasmic reticulum (IC50 = 0.3 μM). It binds to sarcoplasmic reticulum vesicles isolated from normal and malignant hyperthermia-susceptible (MHS) pigs with Kd values of 0.3 and 0.09 μM, respectively. Dantrolene reduces spontaneous calcium wave frequency and amplitude in the presence of calmodulin in isolated mouse cardiomyocytes with IC50 values of 0.42 and 0.19 μM, respectively. It reduces the magnitude of electrically stimulated twitch tensions in isolated rat extensor digitorum longus and soleus muscles (IC50 = 3 μg/ml) and MHS pigs (ED50 = 0.85 mg/kg). Formulations containing dantrolene have been used in the treatment of malignant hyperthermia.
• Uses: Skeletal muscle relaxant;Blocker of Ca2+ release Dantrolene Sodium Salt is a skeletal muscle relaxant, which inhibits intracellular Ca 2+release from the sarcoplasmic reticulum.

Technology Process of Dantrolene sodium

There total 2 articles about Dantrolene sodium 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: 100.0%

dantrolene (7261-97-4) → 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt (14663-23-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 3h;

DOI:10.1007/BF00766662

Reference yield:

5-(4-nitrophenyl)-2-furaldehyde (7147-77-5) → 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt (14663-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / H₂O; dimethylformamide

2: 100 percent / CH₃ONa / methanol / 3 h / 20 °C

With sodium methylate; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1007/BF00766662

Reference yield: 98.0%

1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidine-dione sodium salt (14663-23-1) → dantrolene (7261-97-4)

Guidance literature:

With acetic acid; In N,N-dimethyl-formamide; at 20 ℃;

upstream raw materials:

dantrolene

5-(4-nitrophenyl)-2-furaldehyde

Downstream raw materials:

dantrolene

Refernces