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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:57 UTC
HMDB IDHMDB0015350
Secondary Accession Numbers
  • HMDB15350
Metabolite Identification
Common NameDantrolene
DescriptionDantrolene is only found in individuals that have used or taken this drug.Chemically, dantrolene is a hydantoin derivative, but does not exhibit antiepileptic activity like other hydantoin derivates such as phenytoin.Dantrolene depresses excitation-contraction coupling in skeletal muscle by binding to the ryanodine receptor 1, and decreasing intracellular calcium concentration. Ryanodine receptors mediate the release of calcium from the sarcoplasmic reticulum, an essential step in muscle contraction.
Structure
Data?1582753287
Synonyms
ValueSource
1-((5-(p-Nitrophenyl)furfurylidene)amino)hydantoinChEBI
DantrolenoChEBI
DantrolenumChEBI
Chemical FormulaC14H10N4O5
Average Molecular Weight314.253
Monoisotopic Molecular Weight314.06511945
IUPAC Name1-({[5-(4-nitrophenyl)furan-2-yl]methylidene}amino)imidazolidine-2,4-dione
Traditional Namesodium, dantrolene
CAS Registry Number7261-97-4
SMILES
[O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=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)
InChI KeyOZOMQRBLCMDCEG-UHFFFAOYSA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point279 - 280 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.08 g/LNot Available
LogP1.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP1.65ALOGPS
logP1.26ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.23ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area120.73 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.87 m³·mol⁻¹ChemAxon
Polarizability29.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.48131661259
DarkChem[M-H]-173.36531661259
DeepCCS[M+H]+174.10230932474
DeepCCS[M-H]-171.74430932474
DeepCCS[M-2H]-205.25630932474
DeepCCS[M+Na]+180.48430932474
AllCCS[M+H]+170.732859911
AllCCS[M+H-H2O]+167.232859911
AllCCS[M+NH4]+173.932859911
AllCCS[M+Na]+174.832859911
AllCCS[M-H]-171.132859911
AllCCS[M+Na-2H]-170.432859911
AllCCS[M+HCOO]-169.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dantrolene[O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=O3998.0Standard polar33892256
Dantrolene[O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=O2870.3Standard non polar33892256
Dantrolene[O-][N+](=O)C1=CC=C(C=C1)C1=CC=C(O1)C=NN1CC(=O)NC1=O3323.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dantrolene,1TMS,isomer #1C[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O3253.9Semi standard non polar33892256
Dantrolene,1TMS,isomer #1C[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O3208.6Standard non polar33892256
Dantrolene,1TMS,isomer #1C[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O4710.8Standard polar33892256
Dantrolene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O3550.3Semi standard non polar33892256
Dantrolene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O3432.6Standard non polar33892256
Dantrolene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CN(N=CC2=CC=C(C3=CC=C([N+](=O)[O-])C=C3)O2)C1=O4600.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dantrolene GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xr-1690000000-d26c38a9d976493f22ba2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dantrolene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dantrolene 15V, Negative-QTOFsplash10-03di-0049000000-a19e7d4f9959ab10cf892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dantrolene 30V, Negative-QTOFsplash10-0udi-0090000000-22c70ff1c5c85bfa53de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dantrolene 60V, Negative-QTOFsplash10-0002-1920000000-858f043b14cd350ebe7b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dantrolene 45V, Negative-QTOFsplash10-0udi-1590000000-dbed64771a911370b0ec2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dantrolene 90V, Negative-QTOFsplash10-0002-1900000000-e90a3c39335b51d5ed542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dantrolene 75V, Negative-QTOFsplash10-0002-1900000000-bfa08bf4fe11a1397edc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dantrolene 60V, Positive-QTOFsplash10-0002-1910000000-2c36c4de7fa561e975cc2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dantrolene 10V, Positive-QTOFsplash10-014i-0019000000-2fc8ae4177ccb56abfab2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dantrolene 20V, Positive-QTOFsplash10-014i-0149000000-a112fe650fdea6c2b6882017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dantrolene 40V, Positive-QTOFsplash10-0002-9650000000-76571330cab68a28e44e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dantrolene 10V, Negative-QTOFsplash10-03di-2009000000-2b189b79919d98a46bdb2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dantrolene 20V, Negative-QTOFsplash10-0006-9000000000-84778de90459e0d432162017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dantrolene 40V, Negative-QTOFsplash10-0006-9000000000-3874c10b014fca6acc212017-07-26Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01219 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01219 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01219
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5290202
KEGG Compound IDC06939
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDantrolene
METLIN IDNot Available
PubChem Compound6914273
PDB IDNot Available
ChEBI ID4317
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Krause T, Gerbershagen MU, Fiege M, Weisshorn R, Wappler F: Dantrolene--a review of its pharmacology, therapeutic use and new developments. Anaesthesia. 2004 Apr;59(4):364-73. [PubMed:15023108 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in calcium channel activity
Specific function:
Communication between transverse-tubules and sarcoplasmic reticulum. Contraction of skeletal muscle is triggered by release of calcium ions from SR following depolarization of T-tubules
Gene Name:
RYR1
Uniprot ID:
P21817
Molecular weight:
565170.7
References
  1. Britt BA, Scott E, Frodis W, Clements MJ, Endrenyi L: Dantrolene--in vitro studies in malignant hyperthermia susceptible (MHS) and normal skeletal muscle. Can Anaesth Soc J. 1984 Mar;31(2):130-54. [PubMed:6704779 ]
  2. Harrison GG: Control of the malignant hyperpyrexic syndrome in MHS swine by dantrolene sodium. 1975. Br J Anaesth. 1998 Oct;81(4):626-9; discussion 625. [PubMed:9924249 ]
  3. Flewellen EH, Nelson TE: Dantrolene dose response in malignant hyperthermia-susceptible (MHS) swine: method to obtain prophylaxis and therapeusis. Anesthesiology. 1980 Apr;52(4):303-8. [PubMed:7362049 ]
  4. Tonner PH, Scholz J, Richter A, Loscher W, Steinfath M, Wappler F, Wlaz P, Hadji B, Roewer N, Schulte am Esch J: Alterations of inositol polyphosphates in skeletal muscle during porcine malignant hyperthermia. Br J Anaesth. 1995 Oct;75(4):467-71. [PubMed:7488490 ]
  5. Zhao X, Weisleder N, Han X, Pan Z, Parness J, Brotto M, Ma J: Azumolene inhibits a component of store-operated calcium entry coupled to the skeletal muscle ryanodine receptor. J Biol Chem. 2006 Nov 3;281(44):33477-86. Epub 2006 Aug 31. [PubMed:16945924 ]
  6. Krause T, Gerbershagen MU, Fiege M, Weisshorn R, Wappler F: Dantrolene--a review of its pharmacology, therapeutic use and new developments. Anaesthesia. 2004 Apr;59(4):364-73. [PubMed:15023108 ]
  7. Gerbershagen MU, Fiege M, Krause T, Agarwal K, Wappler F: [Dantrolene. Pharmacological and therapeutic aspects]. Anaesthesist. 2003 Mar;52(3):238-45. [PubMed:12666006 ]
  8. Paul-Pletzer K, Yamamoto T, Bhat MB, Ma J, Ikemoto N, Jimenez LS, Morimoto H, Williams PG, Parness J: Identification of a dantrolene-binding sequence on the skeletal muscle ryanodine receptor. J Biol Chem. 2002 Sep 20;277(38):34918-23. Epub 2002 Jul 11. [PubMed:12167662 ]
  9. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]