Dantrolene

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Dantrolene.png
Dantrolene chemical structure


Dantrolene

1-(((5-(4-nitrophenyl)-2-furanyl)
methylene)amino)-2,4-imidazolidinedione
CAS number
7261-97-4 or 14663-23-1 (dantrolene sodium)
ATC code
M03CA01
Chemical formula C14H10N4O5
Molecular weight 336
Bioavailability 70%
Metabolism Liver
Elimination half-life 10-12 hours
Excretion Bile, urine
Pregnancy category C (USA)
Legal status Unregulated
Routes of administration oral capsules, intravenous

Dantrolene sodium is a muscle relaxant that is currently the only specific and effective treatment for malignant hyperthermia. It is also used in the management of neuroleptic malignant syndrome, spasticity and ecstasy intoxication.

Contents

Chemistry

Chemically it is a hydantoin derivative, but does not exhibit antiepileptic activity like other hydantoin derivates such as phenytoin.

The related substance azumolene is under development for similar indications. It has a bromine residue instead of the nitrite group, and is 30 times more water-soluble.

Mode of action

Dantrolene depresses excitation-contraction coupling in skeletal muscle by binding to the ryanodine receptor, and decreasing intracellular calcium concentration.

Side-effects

Muscle weakness may persist for several days following treatment. It is potentially hepatotoxic.

Problems

The major problem with dantrolene is its poor water solubility, and ensuing difficulty rapidly preparing intravenous solutions in emergency situations. It is routinely mixed with mannitol to improve water solubility.

A minor problem with dantrolene is that the preparation is not cheap and only has a shelf life of 2 years. Smaller hospitals may not see a case of malignant hyperthermia for more than a decade at a time but will still routinely order dantrolene just in case a case arises.

Reference

  • Krause T, Gerbershagen MU, Fiege M, Weisshorn R, Wappler F. Dantrolene - a review of its pharmacology, therapeutic use and new developments. Anaesthesia 2004;59:364-73. PMID 15023108.
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