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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:57 UTC
HMDB IDHMDB0014593
Secondary Accession Numbers
  • HMDB14593
Metabolite Identification
Common NameDroperidol
DescriptionDroperidol, also known as droleptan or inapsine, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Droperidol produces an antiemetic effect as evidenced by the antagonism of apomorphine in dogs. Droperidol is a very strong basic compound (based on its pKa). The main actions seem to stem from its potent Dopamine(2) receptor antagonism with minor antagonistic effects on alpha-1 adrenergic receptors as well. Droperidol is a potentially toxic compound. A butyrophenone with general properties similar to those of haloperidol. The intramuscular LD50 of droperidol is 195 mg/kg in mice, 104-110 mg/kg in rats; 97 mg/kg in rabbits and 200 mg/kg in guinea pigs. It may reduce the incidence of epinephrine-induced arrhythmias, but it does not prevent other cardiac arrhythmias.
Structure
Data?1582753197
Synonyms
ValueSource
1-(1-(3-(p-Fluorobenzoyl)propyl)-1,2,3,6-tetrahydro-4-pyridyl)-2-benzimidazolinoneChEBI
1-(1-(4-(p-Fluorophenyl)-4-oxobutyl)-1,2,3,6-tetrahydro-4-pyridyl)-2-benzimidazolinoneChEBI
1-{1-[4-(4-fluoro-phenyl)-4-oxo-butyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-1,3-dihydro-benzoimidazol-2-oneChEBI
1-{1-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydro-4-pyridinyl}-2,3-dihydro-1H-benzo[D]imidazol-2-oneChEBI
DroperidolumChEBI
DroleptanKegg
InapsineKegg
Taylor brand OF droperidolHMDB
DehydrobenzperidolHMDB
Janssen brand OF droperidolHMDB
Kern brand OF droperidolHMDB
DehidrobenzperidolHMDB
Chemical FormulaC22H22FN3O2
Average Molecular Weight379.4274
Monoisotopic Molecular Weight379.169605168
IUPAC Name1-{1-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydropyridin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-one
Traditional Namedroperidol
CAS Registry Number548-73-2
SMILES
FC1=CC=C(C=C1)C(=O)CCCN1CCC(=CC1)N1C(=O)NC2=CC=CC=C12
InChI Identifier
InChI=1S/C22H22FN3O2/c23-17-9-7-16(8-10-17)21(27)6-3-13-25-14-11-18(12-15-25)26-20-5-2-1-4-19(20)24-22(26)28/h1-2,4-5,7-11H,3,6,12-15H2,(H,24,28)
InChI KeyRMEDXOLNCUSCGS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Phenylbutylamine
  • Butyrophenone
  • Benzimidazole
  • Benzoyl
  • Aryl alkyl ketone
  • Halobenzene
  • Fluorobenzene
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Hydropyridine
  • Benzenoid
  • N-substituted imidazole
  • Gamma-aminoketone
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Urea
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145.75 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.097 g/LNot Available
LogP2.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.097 g/LALOGPS
logP3.93ALOGPS
logP3.01ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.72ChemAxon
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.65 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity109.52 m³·mol⁻¹ChemAxon
Polarizability40.31 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ir-3951000000-3ddcefbb8d45f9f67aeaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0209000000-83800a9c755f8223f328Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0900000000-418e20f120e395aac71aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-2888306b46b834e3dd3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-0cff909ec834cc05a2d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00xr-0900000000-f910b21f009854002b17Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001l-0609000000-b071b906d4d1f94ae833Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00kf-0900000000-ac3d815681b1b57a53b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-b2c3fb5ea6889dbf960cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00xr-0900000000-01bdbb9758cd0acb8864Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-09ecdeee9f023e5ac679Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-be69940105e80f5ab869Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-2900000000-9a55a536e908d6236924Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00fr-9800000000-4462513b0f99ffd6ce93Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00b9-9200000000-b61d87593ee28d4b283eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0918000000-1efb9a7c97db08bb65d2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-2900000000-dd5f00934e38a7c6ddbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0119000000-d5120d98afdcbaa0059bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0944000000-f0624282e21787fbbdd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4921000000-fc1d95a1409cfea060f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0109000000-36f79ce0bfee2b1fc209Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1519000000-e95399c58996c7c32264Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-09ec31ccf84a44cf42f1Spectrum
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 DB00450 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00450 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00450
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3056
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDroperidol
METLIN IDNot Available
PubChem Compound3168
PDB IDNot Available
ChEBI ID4717
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Grip G, Svensson BA, Gordh T Jr, Post C, Hartvig P: Histopathology and evaluation of potentiation of morphine-induced antinociception by intrathecal droperidol in the rat. Acta Anaesthesiol Scand. 1992 Feb;36(2):145-52. [PubMed:1549935 ]
  2. Hamik A, Peroutka SJ: Differential interactions of traditional and novel antiemetics with dopamine D2 and 5-hydroxytryptamine3 receptors. Cancer Chemother Pharmacol. 1989;24(5):307-10. [PubMed:2527092 ]
  3. Larson MD: The effect of antiemetics on pupillary reflex dilation during epidural/general anesthesia. Anesth Analg. 2003 Dec;97(6):1652-6. [PubMed:14633536 ]
  4. Gao HR, Shi TF, Yang CX, Zhang D, Zhang GW, Zhang Y, Jiao RS, Zhang H, Xu MY: The effect of dopamine on pain-related neurons in the parafascicular nucleus of rats. J Neural Transm (Vienna). 2010 May;117(5):585-91. doi: 10.1007/s00702-010-0398-3. Epub 2010 Apr 1. [PubMed:20358234 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Zupko I, Janossy K, Maul K, Marki A, Falkay G: Alpha-adrenergic blockade: a possible mechanism of tocolytic action of certain benzodiazepines in a postpartum rat model in vivo. Life Sci. 2003 Jan 24;72(10):1093-102. [PubMed:12505540 ]