CHEBI:4717 - droperidol

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ChEBI Name droperidol
ChEBI ID CHEBI:4717
Definition An organofluorine compound that is haloperidol in which the hydroxy group has been eliminated with the introduction of a double bond in the piperidine ring, and the 4-chlorophenyl group has been replaced by a benzimidazol-2-on-1-yl group. It is used in the management of chemotherapy-induced nausea and vomiting, and in conjunction with an opioid analgesic such as fentanyl to maintain the patient in a calm state of neuroleptanalgesia with indifference to surroundings but still able to cooperate with the surgeon.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:252751
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Formula C22H22FN3O2
Net Charge 0
Average Mass 379.42740
Monoisotopic Mass 379.170
InChI 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)
InChIKey RMEDXOLNCUSCGS-UHFFFAOYSA-N
SMILES Fc1ccc(cc1)C(=O)CCCN1CCC(=CC1)n1c2ccccc2[nH]c1=O
Roles Classification
Biological Role(s): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
Application(s): antiemetic
A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
anaesthesia adjuvant
Any substance that possesses little anaesthetic effect by itself, but which enhances or potentiates the anaesthetic action of other drugs when given at the same time.
first generation antipsychotic
Antipsychotic drugs which can have different modes of action but which tend to be more likely than second generation antipsychotics to cause extrapyramidal motor control disabilities such as body rigidity or Parkinson's disease-type movements; such body movements can become permanent even after treatment has ceased.
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ChEBI Ontology
Outgoing droperidol (CHEBI:4717) has role anaesthesia adjuvant (CHEBI:60807)
droperidol (CHEBI:4717) has role antiemetic (CHEBI:50919)
droperidol (CHEBI:4717) has role dopaminergic antagonist (CHEBI:48561)
droperidol (CHEBI:4717) has role first generation antipsychotic (CHEBI:65190)
droperidol (CHEBI:4717) is a aromatic ketone (CHEBI:76224)
droperidol (CHEBI:4717) is a benzimidazoles (CHEBI:22715)
droperidol (CHEBI:4717) is a organofluorine compound (CHEBI:37143)
IUPAC Name
1-{1-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydropyridin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one
INNs Sources
droperidol ChemIDplus
droperidolum ChemIDplus
Synonyms Sources
1-(1-(3-(p-fluorobenzoyl)propyl)-1,2,3,6-tetrahydro-4-pyridyl)-2-benzimidazolinone ChemIDplus
1-(1-(4-(p-fluorophenyl)-4-oxobutyl)-1,2,3,6-tetrahydro-4-pyridyl)-2-benzimidazolinone ChemIDplus
1-{1-[4-(4-Fluoro-phenyl)-4-oxo-butyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-1,3-dihydro-benzoimidazol-2-one ChEMBL
1-{1-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydro-4-pyridinyl}-2,3-dihydro-1H-benzo[d]imidazol-2-one ChEMBL
Manual Xrefs Databases
966 DrugCentral
D00308 KEGG DRUG
DB00450 DrugBank
Droperidol Wikipedia
LSM-4193 LINCS
US3161645 Patent
View more database links
Registry Numbers Types Sources
548-73-2 CAS Registry Number ChemIDplus
579168 Beilstein Registry Number Beilstein
Last Modified
22 February 2017