1-({[5-(4-Nitrophenyl)furan-2-yl]methylidene}amino)imidazolidine-2,4-dione

HCID 2952
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Basic information

CAS
7261-97-4
Standard SMILES
O=C1CN(N=Cc2ccc(-c3ccc([N+](=O)[O-])cc3)o2)C(=O)N1
InChIKey
OZOMQRBLCMDCEG-UHFFFAOYSA-N
Molecular formula
C14H10N4O5
Average molar mass
314.25 g/mol
Monoisotopic mass
314.06511942

Overview

Dantrolene is 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. It has a role as a ryanodine receptor antagonist, a muscle relaxant and a neuroprotective agent. It is an imidazolidine-2,4-dione and a hydrazone. It is a conjugate acid of a dantrolene(1-).

Names & identifiers

Preferred name
1-({[5-(4-Nitrophenyl)furan-2-yl]methylidene}amino)imidazolidine-2,4-dione
IUPAC
1-[[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione

Names & synonyms

1-({[5-(4-nitrophenyl)furan-2-yl]methylidene}amino)imidazolidine-2,4-dioneC14H10N4O5Spectrum_001537Prestwick0_000291Prestwick1_000291Spectrum2_001180Spectrum3_001567Spectrum4_000163CBiol_001748SCHEMBL56848KBioGR_000025KBioGR_000645
Show more names
KBioSS_000025KBioSS_002017DivK1c_000898SPBio_001199SPBio_002441orb1220126CHEMBL1741132KBio1_000898

Database identifiers

CAS
7261-97-4
PubChem CID
2952
DTXSID
DTXSID7022881
ChEMBL
CHEMBL1741132
ChEBI
CHEBI:4317

Properties

Computed structural propertiesFilling in

XLogP
1.7
Topological polar surface area
121 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
6
Rotatable bonds
3
Heavy atoms
23

Experimental & physicochemical properties

LogP1.7
Solubility8.05e-02 g/L
Human DrugsPharmaceuticals
Melting Point279 - 280 °C
Physical DescriptionSolid
Collision Cross Section180.0 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID4044585]

Chemistry & industry

Pharmacology

Cellular LocationsMembrane

Uses & manufacturing

Use ClassificationPharmaceuticals

Related reactions

1 records
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Compound notes

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