CHEBI:4317 - dantrolene

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ChEBI Name dantrolene
Definition The hydrazone resulting from the formal condensation of 5-(4-nitrophenyl)furfural with 1-aminohydantoin. A ryanodine receptor antagonist used for the relief of chronic severe spasticity and malignant hyperthermia.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C14H10N4O5
Net Charge 0
Average Mass 314.257
Monoisotopic Mass 314.06512
InChI InChI=1S/C14H10N4O5/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)
SMILES C1(NC(=O)CN1N=C(C=2OC(C=3C=CC([N+]([O-])=O)=CC3)=CC2)[H])=O
Roles Classification
Biological Role(s): ryanodine receptor antagonist
A ryanodine receptor modulator which deactivates the receptor.
Application(s): muscle relaxant
A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
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ChEBI Ontology
Outgoing dantrolene (CHEBI:4317) has role muscle relaxant (CHEBI:51371)
dantrolene (CHEBI:4317) has role neuroprotective agent (CHEBI:63726)
dantrolene (CHEBI:4317) has role ryanodine receptor antagonist (CHEBI:146223)
dantrolene (CHEBI:4317) is a hydrazone (CHEBI:38532)
dantrolene (CHEBI:4317) is a imidazolidine-2,4-dione (CHEBI:24628)
dantrolene (CHEBI:4317) is conjugate acid of dantrolene(1−) (CHEBI:59697)
Incoming dantrolene(1−) (CHEBI:59697) is conjugate base of dantrolene (CHEBI:4317)
INNs Sources
dantrolene ChemIDplus
dantroleno ChemIDplus
dantrolenum ChemIDplus
Synonyms Sources
1-((5-(p-nitrophenyl)furfurylidene)amino)hydantoin ChemIDplus
Manual Xrefs Databases
DB01219 DrugBank
NL6612588 Patent
US3415821 Patent
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Registry Numbers Types Sources
705189 Beilstein Registry Number Beilstein
7261-97-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11934664 PubMed citation Europe PMC
18696266 PubMed citation Europe PMC
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31918212 PubMed citation Europe PMC
32016838 PubMed citation Europe PMC
32060500 PubMed citation Europe PMC
8797628 PubMed citation Europe PMC
Last Modified
25 February 2020
General Comment
2011-01-10 Dantrolene is a direct-acting skeletal muscle relaxant, and is used as the hemiheptahydrate of the sodium salt for the treatment of malignant hyperthermia (a rare but potentially fatal syndrome associated with general anaesthesia in which a rapid increase in calcium concentration in muscle cytoplasm results in a series of metabolic disturbances), for the relief of chronic, severe spasticity, and for the control of muscle spasm in the treatment of tetanus.