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Encyclopedia > Dantrolene
Dantrolene
Systematic (IUPAC) name
1-{[5-(4-nitrophenyl)-2-furyl]methylideneamino}
imidazolidine-2,4-dione
Identifiers
CAS number 7261-97-4
ATC code M03CA01
PubChem 2952
DrugBank APRD00901
Chemical data
Formula C14H10N4O5 
Mol. mass 314.253 g/mol
Pharmacokinetic data
Bioavailability 70%
Metabolism Liver
Half life  ?
Excretion Biliary, renal
Therapeutic considerations
Pregnancy cat.

C(US) Image File history File links This is a lossless scalable vector image. ... Image File history File links Size of this preview: 800 × 344 pixelsFull resolution (1000 × 430 pixel, file size: 85 KB, MIME type: image/png) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The kidneys are organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status
Routes Oral, 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, muscle spasticity (e.g. after strokes, in paraplegia, cerebral palsy, or patients with multiple sclerosis), ecstasy intoxication, and 2,4-dinitrophenol poisoning. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Intravenous therapy or IV therapy is the giving of liquid substances directly into a vein. ... Malignant hyperthermia (MH or MHS for malignant hyperthermia syndrome, or malignant hyperpyrexia due to anesthesia) is a rare life-threatening condition that is triggered by exposure to drugs used for general anaesthesia, such as volatile anaesthetics or the depolarizing muscle relaxant suxamethonium chloride. ... Neuroleptic malignant syndrome (NMS) is a life-threatening, neurological disorder most often caused by an adverse reaction to neuroleptic or antipsychotic drugs. ... Spasticity is a disorder of the bodys motor system in which certain muscles are continuously contracted. ... Stroke (or cerebrovascular accident or CVA) is the clinical designation for a rapidly developing loss of brain function due to an interruption in the blood supply to all or part of the brain. ... Paraplegia is a condition in which the lower part of a persons body is paralyzed and cannot willfully function. ... This article or section is in need of attention from an expert on the subject. ... MDMA (3,4-methylenedioxymethamphetamine), most commonly known by the street names ecstasy or XTC (for more names see the full list), is a synthetic entactogen of the phenethylamine family, whose primary effect is believed to be the stimulation of secretion as well as inhibition of re-uptake of large amounts... 2,4-Dinitrophenol (DNP), C6H4N2O5, is a cellular metabolic poison. ...

Contents

Chemistry

Chemically it is a hydantoin derivative, but does not exhibit antiepileptic activity like other hydantoin derivates such as phenytoin. Hydantoin, which is also known as glycolylurea, is a heterocyclic organic compound which can be thought of as a cyclic double-condensation reaction product of glycolic acid and urea. ... Phenytoin sodium (marketed as Dilantin® in the USA and as Epanutin® in the UK, by Parke-Davis, now part of Pfizer) is a commonly used antiepileptic. ...


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. General Name, Symbol, Number bromine, Br, 35 Chemical series halogens Group, Period, Block 17, 4, p Appearance gas/liquid: red-brown solid: metallic luster Atomic mass 79. ... // Definition The nitrite ion is NO2−. A nitrite compound is one that contains this group, either an ionic compound, or an analogous covalent one. ...


Mode of action

Dantrolene depresses excitation-contraction coupling in skeletal muscle by binding to the ryanodine receptor, and decreasing intracellular calcium concentration. // Excitation-contraction (EC) coupling is a term coined in 1952 to describe the physiological process of converting an electrical stimulus to mechanical response [1]. This process is fundamental to muscle physiology, whereby the electrical stimulus is usually an action potential and the mechanical response is contraction. ... This article or section does not cite any references or sources. ... Molecular binding is a method of molecular interaction to bind together or separate two or more molecules, and is important in the development of new medical drugs and other chemicals. ... Ryanodine receptors form a class of calcium channels in various forms of muscle. ... In cell biology, molecular biology and related fields, the word intracellular means inside the cell. It is used in contrast to extracellular (outside the cell). ... General Name, Symbol, Number calcium, Ca, 20 Chemical series alkaline earth metals Group, Period, Block 2, 4, s Appearance silvery white Standard atomic weight 40. ...


Contraindications

  • preexisting liver disease
  • compromised lung function
  • severe cardiovascular impairment
  • known hypersensitivity to dantrolene
  • pediatric patients under 5 years of age
  • whenever good muscular balance/strength is needed to maintain an upright position, motoric function, or proper neuromuscular balance

If the indication is a medical emergency such as malignant hyperthermia, the only significant contraindication is hypersensitivity. A medical emergency is an injury or illness that poses an immediate threat to a persons health or life which requires help from a doctor or hospital. ...


Pregnancy and lactation

  • Pregnancy: Adequate human studies are lacking, therefore the drug should be given in pregnant women only if clearly indicated.
  • Lactation: Dantrolene should not be given to breastfeeding mothers. If a treatment is necessary, breastfeeding should be terminated.

Side effects

CNS side effects are quite frequently noted and encompass speech and visual disturbances, mental depression and confusion, hallucinations, headache, insomnia and exacerbation or precipitation of seizures, and increased nervousness. Infrequent cases of respiratory depression or a feeling of suffocation have been observed. Dantrolene often causes sedation severe enough to incapacitate the patient to drive or operate machinery. An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ...


Gastrointestinal effects include bad taste, anorexia, nausea, vomiting, abdominal cramps, and diarrhea.


Hepatic side effects may be seen either as asymptomatic elevation of liver enzymes and/or bilirubin or, most severe, as fatal and nonfatal hepatitis. The risk of hepatitis is associated with the duration of treatment and the daily dose. In patients treated for hyperthermia, no liver toxicity has been observed so far. Liver function tests (LFTs or LFs), are groups of clinical biochemistry laboratory blood assays designed to give a doctor or other health professional information about the state of a patients liver. ... Hepatitis (plural hepatitides) implies injury to liver characterised by presence of inflammatory cells in the liver tissue. ...


Pleural effusion with pericarditis (oral treatment only), rare cases of bone marrow damage, diffuse myalgias, backache, dermatologic reactions, transient cardiovascular reactions, and crystalluria have additionally been seen. Muscle weakness may persist for several days following treatment. Pleural effusion Chest x-ray of a pleural effusion. ... Grays Anatomy illustration of cells in bone marrow. ... Myalgia means muscle pain and is a symptom of many diseases and disorders. ... Crystalluria refers to crystals found in the urine when performing a urine test. ...


Mutagenicity and carcinogenity

Dantrolene gave positive results in animal high dose studies (with and without enzymatic activation) regarding mutagenicity and carcinogenity. No evidence for human mutagenicity and carcinogenity has been found during the long years of clinical experience.


Drug interactions

  • Calcium channel blockers of the diltiazem/verapamil type: Intravenous treatment with dantrolene and concomitant calcium channel blocker treatment may lead to severe cardiovascular collapse, arrhythmias, myocardial depressions, and hyperkalemia.
  • Vecuronium bromide: Neuromuscular blockade is potentiated.
  • CNS depressants: Sedative action is potentiated. Benzodiazepines may also cause additive muscle weakness.
  • Estrogens: May enhance liver toxicity of dantrolene in women over 35 years of age.

Calcium channel blockers are a class of drugs with effects on many excitable cells of the body, like the muscle of the heart, smooth muscles of the vessels or neuron cells. ... Diltiazem is a member of the group of drugs known as Benzothiapines , which are a class of calcium channel blockers, used in the treatment of hypertension, angina pectoris, and some types of arrhythmia. ... Verapamil (brand names: Isoptin®, Verelan®, Calan®) is a medical drug that acts as an L-type calcium channel blocker. ... Vecuronium Bromide is a muscle relaxant in the category of non depolarising neuromuscular blocking agents. ... It has been suggested that this article or section be merged with sedative. ... Alprazolam 2mg tablets The benzodiazepines (pronounced , or benzos for short) are a class of psychoactive drugs considered as minor tranquilizers with varying hypnotic, sedative, anxiolytic, anticonvulsant, muscle relaxant and amnesic properties, which are brought on by slowing down the central nervous system. ... Estriol. ...

External references

  • AHFS Database online
  • 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.
  • http://www.kompendium.ch/MonographieTxt.aspx?lang=de&MonType=fi Swiss Drug Compendium on oral Dantrolene (German)

  Results from FactBites:
 
Dantrolene - Wikipedia, the free encyclopedia (444 words)
Dantrolene sodium is a muscle relaxant that is currently the only specific and effective treatment for malignant hyperthermia.
Dantrolene can also be tried to treat malignant neuroleptic syndrome, because some patients have reacted favourably.
Dantrolene depresses excitation-contraction coupling in skeletal muscle by binding to the ryanodine receptor, and decreasing intracellular calcium concentration.
  More results at FactBites »

 
 

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