dantrolene   Click here for help

GtoPdb Ligand ID: 4172

Synonyms: Agilus® | Dantrium® | F-368 | F-440 | Ryanodex®
Approved drug
dantrolene is an approved drug (FDA (1974))
Compound class: Synthetic organic
Comment: Dantrolene inhibits ryanodine receptor subtypes 1 and 3 (RyR1, and RyR3). The structure of dantrolene is commonly represented in the literature with charges, and it is this structure that we show here and link to in PubChem. However, the FDA and INN documents represent the compound without the charge.
Marketed formulations may contain dantrolene sodium (PubChem CID 6604100).
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 118.05
Molecular weight 314.07
XLogP 1.69
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C1CN(C(=O)N1)N=Cc1ccc(o1)c1ccc(cc1)[N+](=O)[O-]
Isomeric SMILES O=C1CN(C(=O)N1)/N=C/c1ccc(o1)c1ccc(cc1)[N+](=O)[O-]
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)/b15-7+
InChI Key OZOMQRBLCMDCEG-VIZOYTHASA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1974)
IUPAC Name Click here for help
1-[[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione
International Nonproprietary Names Click here for help
INN number INN
2317 dantrolene
Synonyms Click here for help
Agilus® | Dantrium® | F-368 | F-440 | Ryanodex®
Database Links Click here for help
CAS Registry No. 7261-97-4 (source: Scifinder)
ChEBI CHEBI:4317
ChEMBL Ligand CHEMBL1201288
DrugBank Ligand DB01219
DrugCentral Ligand 780
GtoPdb PubChem SID 178100992
PubChem CID 6914273
Search Google for chemical match using the InChIKey OZOMQRBLCMDCEG-VIZOYTHASA-N
Search Google for chemicals with the same backbone OZOMQRBLCMDCEG
Search PubMed clinical trials dantrolene
Search PubMed titles dantrolene
Search PubMed titles/abstracts dantrolene
UniChem Compound Search for chemical match using the InChIKey OZOMQRBLCMDCEG-VIZOYTHASA-N
UniChem Connectivity Search for chemical match using the InChIKey OZOMQRBLCMDCEG-VIZOYTHASA-N
Wikipedia Dantrolene

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MedChemExpress
Dantrolene (links to external site)
Cat. No. HY-12542