2816. Dantrolene

Nomenclature

CAS number: 7261-97-4
1-[[[5-(4-Nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidinedione; 1-[[5-(p-nitrophenyl)furfurylidene]amino]hydantoin.
C14H10N4O5; mol wt 314.25.
C 53.51%, H 3.21%, N 17.83%, O 25.46%.

Description and 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); of pharmacology and clinical indications: T. Krause et al., Anaesthesia 59, 364-373 (2004).

Chemical structure

Properties

Crystals from aqueous DMF, mp 279-280°.

Derivative

Sodium salt hemiheptahydrate.

Nomenclature

CAS number: 24868-20-0; 14663-23-1 (anhydrous)
F-440; Dantamacrin (Procter & Gamble); Dantrium (Procter & Gamble); Dantrolen (Procter & Gamble).
C14H9N4NaO5.3 1/2 H2O; mol wt 399.29.
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. pKa 7.5. LD50 (calculated as base) orally in mice: 1110 mg/kg (Ellis).

Therapeutic Category

Muscle relaxant (skeletal); in treatment of malignant hyperthermia.

Therapeutic Category (Veterinary)

Muscle relaxant (skeletal).

Keywords

Muscle Relaxant (Skeletal)