Dantrolene (CED0004234)

Record Information

Version

1.0

Creation Date

2016-05-25 18:26:06 UTC

Update Date

2026-08-19 04:10:23 UTC

Accession Number

CHEM022263

Identification

Common Name

Dantrolene

Class

Small Molecule

Description

Dantrolene is an organic compound with the chemical formula C14H10N4O5 and an average molecular weight of 314.26 g/mol. Dantrolene belongs to the imidazolidines, a subclass of azolidines within the organic compounds. In terms of biological activity, it acts as an antagonist of the Ryanodine receptor 1 (RYR1). The substance is associated with six recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as a muscle relaxant. Other recorded sources include drinking water and water supply, food preservation in food processing and cookware, and tobacco smoke filters in household cleaning and consumer products. Additionally, it is found in electrical and electronic equipment, specifically antennas and electrically stimulated smoking devices. Exposure to this compound occurs through oral and intravenous routes.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
F-368SID90341114	ChEMBL
Dantrolene sodium	MeSH
Dantrolene	MeSH
Dantrium	MeSH
Sodium, dantrolene	MeSH

Chemical Formula

C₁₄H₁₀N₄O₅

Average Molecular Mass

314.257 g/mol

Monoisotopic Mass

314.065 g/mol

CAS Registry Number

7261-97-4

IUPAC Name

4-hydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]-2,5-dihydro-1H-imidazol-2-one

Traditional Name

4-hydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]-5H-imidazol-2-one

SMILES

[H]\C(=N/N1CC(O)=NC1=O)C1=CC=C(O1)C1=CC=C(C=C1)N(=O)=O

InChI Identifier

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)/b15-7+

InChI Key

OZOMQRBLCMDCEG-VIZOYTHASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Hydantoins

Alternative Parents

Substituents

Hydantoin
Alpha-amino acid or derivatives
Nitrobenzene
Nitroaromatic compound
Monocyclic benzene moiety
Semicarbazone
Benzenoid
Heteroaromatic compound
Dicarboximide
Furan
Semicarbazide
Organic nitro compound
C-nitro compound
Carbonic acid derivative
Oxacycle
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic zwitterion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.064 g/L	ALOGPS
logP	1.47	ALOGPS
logP	1.62	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	5.19	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	124.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.2 m³·mol⁻¹	ChemAxon
Polarizability	30.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0019000000-2fc8ae4177ccb56abfab	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0149000000-a112fe650fdea6c2b688	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-9650000000-76571330cab68a28e44e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-2009000000-2b189b79919d98a46bdb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9000000000-84778de90459e0d43216	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9000000000-3874c10b014fca6acc21	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
1243.0	Log mg/kg	[700:2200]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
115	Drinking water	Drinking water & water supply	Not Available
365	Muscle relaxants	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
615	Eye Makeup Products	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
618	Lip Makeup Products	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Dantrolene Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	78.3163
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	162.238
Click to view 3D structure	Endolysin	P00720	Enterobacteria phage T4	Predicted (SEA)	8.87481
Click to view 3D structure	Nonstructural protein 1	Q194T2	Influenza A virus	Predicted (SEA)	34.1758
Click to view 3D structure	Fatty acid synthase	P49327	Humans	Predicted (SEA)	87.0354
Click to view 3D structure	Dual specificity protein phosphatase 3	P51452	Humans	Predicted (SEA)	91.395
Click to view 3D structure	Envelope glycoprotein gp160	Q6QLK5	Human immunodeficiency virus 1	Predicted (SEA)	17.5161
Click to view 3D structure	ATP-dependent molecular chaperone HSP82	C4YTQ8	Candida albicans (strain WO-1) (Yeast)	Predicted (SEA)	296.138
Click to view 3D structure	Protein max	P61244	Humans	Predicted (SEA)	11.9888
Click to view 3D structure	G-protein coupled receptor 55	Q9Y2T6	Humans	Predicted (SEA)	291.0
Click to view 3D structure	Small ubiquitin-related modifier 1	P63165	Humans	Predicted (SEA)	267.801
Click to view 3D structure	Toll-like receptor 9	Q9NR96	Humans	Predicted (SEA)	242.267
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	4612.1
Click to view 3D structure	Beta Lactamase	Q932Y6	Pseudomonas aeruginosa	Predicted (SEA)	273.406
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P26358	Humans	Predicted (SEA)	436.656
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	3812.51
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 22	Q9Y2R2	Humans	Predicted (SEA)	223.116
Click to view 3D structure	DNA damage-inducible transcript 3 protein	P35639	Mus musculus	Predicted (SEA)	1191.33
Click to view 3D structure	X-box-binding protein 1	P17861	Humans	Predicted (SEA)	1192.81
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	2056.0
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	2017.0
Click to view 3D structure	Ribosomal protein S6 kinase alpha-3	P51812	Humans	Predicted (SEA)	3696.98
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	1335.19
Click to view 3D structure	26S proteasome non-ATPase regulatory subunit 14	O00487	Humans	Predicted (SEA)	89.6045
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 11	Q06124	Humans	Predicted (SEA)	635.328