rocuronium (CED0002446)

Record Information
Version1.0
Creation Date2016-06-03 10:21:11 UTC
Update Date2026-08-22 11:02:54 UTC
Accession NumberCHEM042868
Identification
Common Namerocuronium
ClassSmall Molecule
Description
Rocuronium is an organic compound with the chemical formula C32H53N2O4. Rocuronium belongs to the steroid esters, a subclass of steroids and steroid derivatives within the organic compounds. With an average molecular weight of 529.77 g/mol, rocuronium is a heavy molecule. This substance is recorded as being found in or released from three distinct sources: healthcare, pharmaceuticals & veterinary products specifically as muscle relaxants; electrical & electronic equipment including television systems; and household cleaning & consumer products under other smoking requisites. The recorded route of exposure for this compound is intravenous. In terms of biological activity, rocuronium interacts with three recorded protein targets. It acts as an antagonist of the neuronal acetylcholine receptor subunit alpha-2 (CHRNA2), the muscarinic acetylcholine receptor M2 (CHRM2), and the 5-hydroxytryptamine receptor 3A (HTR3A). As a member of the lipids and lipid-like molecules superclass, it functions within these specified pharmacological pathways.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Rocuronium bromideHMDB
EsmeronHMDB
EsmeroneHMDB
1-(17-(Acetoyl)-3-hydroxy-2-(4-morpholinyl)androstan-16-yl)-1-(2-propenyl)pyrrolidiniumHMDB
Pyrrolidinium, 1-((2beta,3alpha,5alpha,16beta,17beta)-17-(acetyloxy)-3-hydroxy-2-(4-morpholinyl)androstan-16-yl)-1-(2-propenyl)-, bromideHMDB
ZemuronHMDB
Chemical FormulaC32H53N2O4
Average Molecular Mass529.774 g/mol
Monoisotopic Mass529.401 g/mol
CAS Registry Number143558-00-3
IUPAC Name1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-14-(acetyloxy)-5-hydroxy-2,15-dimethyl-4-(morpholin-4-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl]-1-(prop-2-en-1-yl)pyrrolidin-1-ium
Traditional Namerocuronium
SMILES[H][C@@]12C[C@@H]([C@H](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)[C@H](C[C@]12C)N1CCOCC1)[N+]1(CC=C)CCCC1
InChI IdentifierInChI=1S/C32H53N2O4/c1-5-14-34(15-6-7-16-34)28-20-26-24-9-8-23-19-29(36)27(33-12-17-37-18-13-33)21-32(23,4)25(24)10-11-31(26,3)30(28)38-22(2)35/h5,23-30,36H,1,6-21H2,2-4H3/q+1/t23-,24+,25-,26-,27-,28-,29-,30-,31-,32-/m0/s1
InChI KeyYXRDKMPIGHSVRX-OOJCLDBCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • N-alkylpyrrolidine
  • Oxazinane
  • Morpholine
  • Quaternary ammonium salt
  • Pyrrolidine
  • Tetraalkylammonium salt
  • Cyclic alcohol
  • Secondary alcohol
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Dialkyl ether
  • Ether
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Organic salt
  • Organonitrogen compound
  • Organooxygen compound
  • Organic cation
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.8e-05 g/LALOGPS
logP2.71ALOGPS
logP-0.33ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)14.59ChemAxon
pKa (Strongest Basic)7.96ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity161.65 m³·mol⁻¹ChemAxon
Polarizability62.87 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-1439520000-efed63eab6ab3907f152Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0udr-4104980000-d7ca5ec71ab6ac306ceeNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1000490000-6840ba568de48e48ae41Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03du-3021940000-bb83313d5a8374696e7eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9116600000-af679250dcee62275d4fNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
234.0Log mg/kg[130:420]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
365Muscle relaxantsHealthcare, pharmaceuticals & veterinary productsNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
Pathways
1 pathway
Rocuronium Drug Metabolism Action Pathway
Rocuronium Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureEukaryotic initiation factor 4A-IP60843Mus musculusPredicted (SEA)0.311397
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)69.208
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)33.8644
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 2Q11205Rattus norvegicusPredicted (SEA)18.2167
Click to view 3D structureCycloartenol-C-24-methyltransferaseQ9LM02Arabidopsis thalianaPredicted (SEA)6.38364
Click to view 3D structureGamma-aminobutyric acid type B receptor subunit 1Q9Z0U4Rattus norvegicusPredicted (SEA)10.1204
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)223.349
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)31.4511
Click to view 3D structureNeurogenic locus notch homolog protein 1Q01705Mus musculusPredicted (SEA)3.58106
Click to view 3D structureCytochrome P450 7B1O75881HumansPredicted (SEA)10.3539
Solute carrier family 22 member 2 structureClick to view 3D structureSolute carrier family 22 member 2O15244HumansPredicted (SEA)79.0948
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)251.92
Click to view 3D structurePotassium-transporting ATPase alpha chain 2P54707HumansPredicted (SEA)10.9767
Click to view 3D structureAndrogen receptorP19091Mus musculusPredicted (SEA)110.39
Vitamin D3 receptor structureClick to view 3D structureVitamin D3 receptorP11473HumansPredicted (SEA)860.545
Click to view 3D structureMultidrug and toxin extrusion protein 1Q96FL8HumansPredicted (SEA)306.337
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)2111.58
Click to view 3D structureCMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 1Q11201HumansPredicted (SEA)15.8034
Glucose-6-phosphate 1-dehydrogenase structureClick to view 3D structureGlucose-6-phosphate 1-dehydrogenaseP11413HumansPredicted (SEA)28.8042
Click to view 3D structureGlucose-6-phosphate 1-dehydrogenaseQ9GRG7Trypanosoma bruceiPredicted (SEA)26.313
3-oxo-5-alpha-steroid 4-dehydrogenase 2 structureClick to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 2P31213HumansPredicted (SEA)72.1662
Click to view 3D structureNuclear receptor subfamily 1 group I member 3O35627Mus musculusPredicted (SEA)18.606
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansPredicted (SEA)2550.81
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)5875.83
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)98.0122
Concentrations
Not Available
External Links
DrugBank IDDB00728
HMDB IDHMDB0014866
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRocuronium
Chemspider ID390053
ChEBI ID8884
PubChem Compound ID441290
Kegg Compound IDC07556
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Agoston S, Vandenbrom RH, Wierda JM: Clinical pharmacokinetics of neuromuscular blocking drugs. Clin Pharmacokinet. 1992 Feb;22(2):94-115.
2. Wicks TC: The pharmacology of rocuronium bromide (ORG 9426). AANA J. 1994 Feb;62(1):33-8.
3. Khuenl-Brady KS, Sparr H: Clinical pharmacokinetics of rocuronium bromide. Clin Pharmacokinet. 1996 Sep;31(3):174-83.
4. Alvarez-Gomez JA: [Rocuronium]. Rev Esp Anestesiol Reanim. 1997 Oct;44(8):310-4.
5. Sparr HJ, Beaufort TM, Fuchs-Buder T: Newer neuromuscular blocking agents: how do they compare with established agents? Drugs. 2001;61(7):919-42.
6. Hemmerling TM, Russo G, Bracco D: Neuromuscular blockade in cardiac surgery: an update for clinicians. Ann Card Anaesth. 2008 Jul-Dec;11(2):80-90.
7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
8. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
9. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
10. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
11. The lipid handbook with CD-ROM
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=10594422
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=11123992
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=16764586
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=17667569
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23238810
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23372882
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23544332
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23560186
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23641322
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23678983
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23859417
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24147111
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=29368335
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=7741284
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=8279688