CHEBI:4317 - dantrolene

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ChEBI Name dantrolene
ChEBI ID CHEBI:4317
Definition The hydrazone resulting from the formal condensation of 5-(4-nitrophenyl)furfural with 1-aminohydantoin.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C14H10N4O5
Net Charge 0
Average Mass 314.25300
Monoisotopic Mass 314.065
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)
InChIKey OZOMQRBLCMDCEG-UHFFFAOYSA-N
SMILES [O-][N+](=O)c1ccc(cc1)-c1ccc(C=NN2CC(=O)NC2=O)o1
Roles Classification
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.
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ChEBI Ontology
Outgoing dantrolene (CHEBI:4317) has role muscle relaxant (CHEBI:51371)
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)
IUPAC Name
1-({[5-(4-nitrophenyl)furan-2-yl]methylidene}amino)imidazolidine-2,4-dione
INNs Sources
dantrolene ChemIDplus
dantroleno ChemIDplus
dantrolenum ChemIDplus
Synonyms Sources
1-((5-(p-nitrophenyl)furfurylidene)amino)hydantoin ChemIDplus
Dantrolene KEGG COMPOUND
Database Links Databases
C06939 KEGG COMPOUND
D02347 KEGG DRUG
DB01219 DrugBank
LSM-3823 LINCS
NL6612588 Patent
US3415821 Patent
View more database links
Registry Numbers Types Sources
705189 Beilstein Registry Number Beilstein
7261-97-4 CAS Registry Number ChemIDplus
Last Modified
22 February 2017
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.