Dantrolene sodium CAS 24868-20-0

Introduction：Basic information about Dantrolene sodium CAS 24868-20-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Dantrolene sodium Basic information

• Product Name: Dantrolene sodium
• Synonyms: Dantrolene sodium hydrate (2:2:7);DANTROLENE SODIUM HYDRATE;2,4-Imidazolidinedione, 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-, sodium salt, hydrate (2:2:7);disodium 3-[(E)-[5-(4-nitrophenyl)-2-furanyl]methylideneamino]-5-oxo-4H-imidazol-2-olate heptahydrate;1-[[[5-(4-NITROPHENYL)-2-FURANYL]METHYLENE]AMINO]-2,4-IMIDAZOLINEDIONE SODIUM SALT;1-[[[5-(4-NITROPHENYL)-2-FURANYL]-METHYLENE]IMINO]2,4-IMIDAZOLIDINEDIONE SODIUM SALT;DANTRIUM;DANTROLENE NA
• CAS: 24868-20-0
• MF: C14H13N4NaO6
• MW: 356.27
• Product Categories: Active Pharmaceutical Ingredients;Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;API;24868-20-0
• Mol File: 24868-20-0.mol

Dantrolene sodium Chemical Properties

• Melting point: >230°C
• storage temp.: Sealed in dry,Store in freezer, under -20°C
• solubility: DMSO (Slightly), Ethyl Acetate (Slightly, Heated, Sonicated)
• form: Solid
• color: Yellow to Dark Yellow
• Major Application: pharmaceutical (small molecule)
• InChI: InChI=1S/C14H10N4O5.Na.H2O.H/c19-13-8-17(14(20)16-13)15-7-11-5-6-12(23-11)9-1-3-10(4-2-9)18(21)22;;;/h1-7H,8H2,(H,16,19,20);;1H2;/b15-7+;;;
• InChIKey: FNWJBGOLSPMRSF-HFUUWOKWSA-N
• SMILES: C(/C1=CC=C(C2C=CC(N(=O)=O)=CC=2)O1)=N\N1C(NC(=O)C1)=O.[NaH].O
• CAS DataBase Reference: 24868-20-0(CAS DataBase Reference)

Safety Information

• Safety Statements: 22-24/25
• WGK Germany: 2
• RTECS: MU3875000
• HS Code: 2934990002
• Storage Class: 11 - Combustible Solids

Dantrolene sodium Usage And Synthesis

Chemical Properties

Orange Powder

Originator

Dantrium,Norwich Eaton ,US,1974

Uses

Dantrolene Sodium Salt Hemiheptahydrate is a muscle relaxant (skeletal). Used in the treatment of malignant hyperthermia.

Definition

ChEBI: A hydrate which is the hemiheptahydrate of anhydrous dantrolene sodium.

Manufacturing Process

5-(p-Nitrophenyl)-2-furaldehyde (40.0 grams, 0.2 mol) is dissolved indimethylformamide. An aqueous solution of 1-aminohydantoin hydrochloride(30.0 grams, 0.2 mol) is added. The solution is chilled and diluted with water.The crude material is collected and recrystallized from aqueousdimethylformamide to yield 10.0 grams (16%). MP 279°-280°C. Thiscompound is then converted to the sodium salt.

Brand name

Dantrium (Procter & Gamble).

Therapeutic Function

Muscle relaxant

Biological Functions

Dantrolene sodium (Dantrium) is used in the treatmentof spasticity due to stroke, spinal injury, multiple sclerosis,or cerebral palsy. It is also the drug of choice in prophylaxisor treatment of malignant hyperthermia.
Susceptibility to malignant hyperthermia is due to arare genetic defect that allows Ca⁺⁺ release from thesarcoplasmic reticulum to open more easily and closeless readily than normal. This leads to a high level ofCa⁺⁺ in the sarcoplasm, which produces muscle rigidity,oxygen consumption, and heat. Dantrolene acts byblocking Ca⁺⁺ release from the sarcoplasmic reticulumand uncoupling excitation from contraction.
Dantrolene is active orally, although its absorption isslow and incomplete. Its biological half-life (t_1/2) is 8.7hours in adults. The drug is metabolized by liver microsomalenzymes and is eliminated in the urine and bile.It is given IV when treating an attack of malignant hyperthermia.The most prominent and often limiting feature ofdantrolene administration is dose-dependent muscleweakness. Other side effects are drowsiness, dizziness,malaise, fatigue, and diarrhea. Symptomatic hepatitis isreported in 0.5% of patients receiving it and fatal hepatitisin up to 0.2%. Contraindications include respiratorymuscle weakness and liver disease. It is suggestedthat patients on dantrolene therapy be given regularliver function tests.

Clinical Use

Oral: Treatment of chronic, severe spasticity of skeletal muscle
IV: Treatment of malignant hyperthermia

Veterinary Drugs and Treatments

In humans, oral dantrolene is indicated primarily for the treatmentassociated with upper motor neuron disorders (e.g., multiple sclerosis,cerebral palsy, spinal cord injuries, etc.). In veterinary medicine,its proposed indications include: the prevention and treatment ofmalignant hyperthermia syndrome in various species, the treatmentof functional urethral obstruction due to increasedexternal urethraltone in dogs and cats, the prevention and treatment of equine postanestheticmyositis (PAM), and equine exertional rhabdomyolysis.It has also been recommended for use in the treatment of bites fromBlack Widow Spiders in small animals and the treatment of porcinestress syndrome.

Drug interactions

Potentially hazardous interactions with other drugs
Avoid with other hepatotoxic medication.

Metabolism

Dantrolene is inactivated by hepatic metabolism in the first instance. There are two alternative pathways. Most of the drug is hydroxylated to 5-hydroxydantrolene. The minor pathway involves nitro-reduction to aminodantrolene, which is then acetylated (compound F-490). The 5-hydroxy metabolite is a muscle relaxant with nearly the same potency as the parent molecule, and may have a longer half-life than the parent compound. Compound F-490 is much less potent and is probably inactive at the concentrations achieved in clinical samples. Metabolites are subsequently excreted in the urine in the ratio of 79 5 hydroxy-dantrolene: 17 compound F-490: 4 unaltered dantrolene (salt or free acid). The proportion of drug excreted in the faeces depends upon dose size.

Dantrolene sodium Preparation Products And Raw materials

• Raw materials: Sodium hydroxide-->1-Aminohydantoin hydrochloride-->5-(4-Nitrophenyl)-2-furaldehyde