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Identification
Name Droperidol
Accession Number DB00450 (APRD00939)
Type small molecule
Groups approved
Description

A butyrophenone with general properties similar to those of haloperidol. It is used 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. It is also used as a premedicant, as an antiemetic, and for the control of agitation in acute psychoses. (From Martindale, The Extra Pharmacopoeia, 29th ed, p593)
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Dehidrobenzperidol
  • Dehydrobenzperidol
  • Deidrobenzperidolo
  • DHBP
  • Dihidrobenzperidol
  • Dridol
  • Droleptan
  • Halkan
  • Inappin
  • Inapsin
  • Inapsine
  • Innovan
  • Innovar
  • Innovar-Vet
  • Inopsin
  • Inoval
  • Leptanal
  • Leptofen
  • McN-JR 4749
  • Properidol
  • Sintodril
  • Sintosian
  • Thalamanol
  • Thalamonal
  • Vetkalm
Brand name mixtures
  • Innovar Inj (Droperidol + Fentanyl Citrate)
  • Innovar-Vet Inj (Droperidol + Fentanyl Citrate)
Categories
  • Antiemetics
  • Adjuvants, Anesthesia
  • Dopamine Antagonists
  • Antipsychotic Agents
CAS number 548-73-2
Weight Average: 379.4274
Monoisotopic: 379.169605168
Chemical Formula C22H22FN3O2
InChI Key InChIKey=RMEDXOLNCUSCGS-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
1-{1-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,6-tetrahydropyridin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-one
SMILES
FC1=CC=C(C=C1)C(=O)CCCN1CCC(=CC1)N1C(=O)NC2=C1C=CC=C2
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Butyrophenones
Substructures
  • Alkanes and Alkenes
  • Benzimidazoles
  • Benzene and Derivatives
  • Butyrophenones
  • Aliphatic and Aryl Amines
  • Halobenzenes
  • Imidazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Benzoyl Derivatives
  • Cyanamides
  • Aryl Halides
  • Acetophenones and Derivatives
  • Ketones
Pharmacology
Indication Droperidol is ssed to produce tranquilization and to reduce the incidence of nausea and vomiting in surgical and diagnostic procedures.
Pharmacodynamics Droperidol produces marked tranquilization and sedation. It allays apprehension and provides a state of mental detachment and indifference while maintaining a state of reflex alertness. Droperidol produces an antiemetic effect as evidenced by the antagonism of apomorphine in dogs. It lowers the incidence of nausea and vomiting during surgical procedures and provides antiemetic protection in the postoperative period. Droperidol potentiates other CNS depressants. It produces mild alpha-adrenergic blockade, peripheral vascular dilatation and reduction of the pressor effect of epinephrine. It can produce hypotension and decreased peripheral vascular resistance and may decrease pulmonary arterial pressure (particularly if it is abnormally high). It may reduce the incidence of epinephrine-induced arrhythmias, but it does not prevent other cardiac arrhythmias.
Mechanism of action The exact mechanism of action is unknown, however, droperidol causes a CNS depression at subcortical levels of the brain, midbrain, and brainstem reticular formation. It may antagonize the actions of glutamic acid within the extrapyramidal system. It may also inhibit cathecolamine receptors and the reuptake of neurotransmiters and has strong central antidopaminergic action and weak central anticholinergic action. It can also produce ganglionic blockade and reduced affective response. The main actions seem to stem from its potent Dopamine(2) receptor antagonism with minor antagonistic effects on alpha-1 adrenergic receptors as well.
Absorption Completely absorbed following intramuscular administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Extensively metabolized.
Route of elimination Not Available
Half life Biphasic distribution. The rapid distribution phase is 1.4 ± 0.5 minutes and the slower distribution phase is 14.3 ± 6.5 minutes. Elimination half-life in adults is 134 ± 13 minutes and may be increased in geriatric patients. In children, it is 101.5 ± 26.4 minutes.
Clearance Not Available
Toxicity The intravenous LD50 of droperidol is 20-43 mg/kg in mice; 30 mg/kg in rats; 25 mg/kg in dogs and 11-13 mg/kg in rabbits. 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. The manifestations of droperidol overdosage are an extension of its pharmacologic actions.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Abraxis pharmaceutical products
  • Astrazeneca lp
  • Hospira inc
  • Luitpold pharmaceuticals inc
  • Smith and nephew solopak div smith and nephew
  • Solopak laboratories inc
  • Watson laboratories inc
  • Akorn inc
Packagers
Dosage forms
Form Route Strength
Solution Intramuscular
Prices
Unit description Cost Unit
Inapsine 2.5 mg/ml ampul 4.59 USD ml
Droperidol 2.5 mg/ml vial 2.04 USD ml
Droperidol 2.5 mg/ml ampul 0.7 USD ml
Patents Not Available
Properties
State solid
Melting point 145.75 oC
Experimental Properties
Property Value Source
water solubility 4.21 mg/L PhysProp
logP 2.8 PhysProp
pKa 7.46 Various sources
Predicted Properties
Property Value Source
water solubility 9.66e-02 g/l ALOGPS
logP 3.93 ALOGPS
logP 3.01 ChemAxon Molconvert
logS -3.59 ALOGPS
pKa 16.39 ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 52.65 ChemAxon Molconvert
rotatable bond count 6 ChemAxon Molconvert
refractivity 109.52 ChemAxon Molconvert
polarizability 40.31 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00308 Link_out
PubChem Compound 3168 Link_out
PubChem Substance 46505291 Link_out
ChemSpider 3056 Link_out
BindingDB 50017705 Link_out
ChEBI 4717 Link_out
ChEMBL 4717 Link_out
Therapeutic Targets Database DAP000412 Link_out
PharmGKB PA449422 Link_out
Drug Product Database 2167832 Link_out
RxList http://www.rxlist.com/cgi/generic3/droperidol.htm Link_out
Drugs.com http://www.drugs.com/cdi/droperidol.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Droperidol Link_out
ATC Codes
  • N01AX01
  • N05AD08
AHFS Codes
  • 28:24.92
PDB Entries Not Available
FDA label Not Available
MSDS show (74 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. D(2) dopamine receptor

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P14416 Link_out
Gene: DRD2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Larson MD: The effect of antiemetics on pupillary reflex dilation during epidural/general anesthesia. Anesth Analg. 2003 Dec;97(6):1652-6. Pubmed
  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. 2010 May;117(5):585-91. Epub 2010 Apr 1. Pubmed

2. Alpha-1A adrenergic receptor

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P35348 Link_out
Gene: ADRA1A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:04

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.