Dantrolene

Title: Dantrolene
CAS Registry Number: 7261-97-4
CAS Name: 1-[[[5-(4-Nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidinedione
Additional Names: 1-[[5-(p-nitrophenyl)furfurylidene]amino]hydantoin
Molecular Formula: C14H10N4O5
Molecular Weight: 314.25
Percent Composition: C 53.51%, H 3.21%, N 17.83%, O 25.46%
Literature References: Direct acting skeletal muscle relaxant; probably inhibits the release of calcium from the sarcoplasmic reticulum of skeletal muscle. Prepn: NL 6612588; Davis, Snyder, US 3415821 (1967, 1968 both to Norwich Pharmacal); Snyder et al., J. Med. Chem. 10, 807 (1967); Frimm et al., Chem. Zvesti 23, 916 (1969). HPLC determn in plasma: M. Lalande et al., J. Chromatogr. 430, 187 (1988). Toxicity data: K. O. Ellis et al., J. Pharm. Sci. 69, 327 (1980). Review of pharmacology: G. G. Harrison, Br. J. Anaesth. 60, 279 (1988); and therapeutic use: A. Ward et al., Drugs 32, 130-168 (1986). Review of efficacy in malignant hyperthermia: R. Ben Abraham et al., Q. J. Med. 90, 13-18 (1997).
Properties: Crystals from aqueous DMF, mp 279-280°.
Melting point: mp 279-280°
Derivative Type: Sodium salt hemiheptahydrate
CAS Registry Number: 24868-20-0; 14663-23-1 (anhydrous)
Manufacturers' Codes: F-440
Trademarks: Dantamacrin (Procter & Gamble); Dantrium (Procter & Gamble)
Molecular Formula: C14H9N4NaO5.3½H2O
Molecular Weight: 399.29
Percent Composition: C 42.11%, H 4.04%, N 14.03%, Na 5.76%, O 34.06%
Properties: Orange powder. Slightly soluble in water; more sol in alkaline soln. LD50 (calculated as base) orally in mice: 1110 mg/kg (Ellis).
Toxicity data: LD50 (calculated as base) orally in mice: 1110 mg/kg (Ellis)
Therap-Cat: Muscle relaxant (skeletal); in treatment of malignant hyperthermia.
Keywords: Muscle Relaxant (Skeletal).
Daphnetin Daphnin Daphnoline Dapiprazole Dapoxetine

Dantrolene
Dantrolene Tanaka et al.svg
Systematic (IUPAC) name
1-{[5-(4-nitrophenyl)-2-furyl]methylideneamino}
imidazolidine-2,4-dione
Clinical data
Trade names Dantrium
AHFS/Drugs.com monograph
Pregnancy cat. C (US)
Legal status  ?
Routes Oral, intravenous
Pharmacokinetic data
Bioavailability 70%
Metabolism Liver
Excretion Biliary, renal
Identifiers
CAS number 7261-97-4 YesY
ATC code M03CA01
PubChem CID 2952
IUPHAR ligand 4172
DrugBank DB01219
ChemSpider 2847 YesY
UNII F64QU97QCR YesY
KEGG D02347 N
ChEBI CHEBI:4317 YesY
ChEMBL CHEMBL1201288 N
Chemical data
Formula C14H10N4O5 
Mol. mass 314.253 g/mol
 N (what is this?)  (verify)

Dantrolene sodium is a muscle relaxant that acts by abolishing excitation-contraction coupling in muscle cells, probably by action on the ryanodine receptor. It is the only specific and effective treatment for malignant hyperthermia, a rare, life-threatening disorder triggered by general anesthesia. It is also used in the management of neuroleptic malignant syndrome, muscle spasticity (e.g. after strokes, in paraplegia, cerebral palsy, or patients with multiple sclerosis), 3,4-methylenedioxymethamphetamine ("ecstasy") intoxication, serotonin syndrome, and 2,4-dinitrophenol poisoning.[1] It is marketed by JHP Pharmaceuticals LLC as Dantrium (in North America) and by Norgine BV as Dantrium, Dantamacrin, or Dantrolen (in Europe).