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Details

Stereochemistry RACEMIC
Molecular Formula C22H22FN3O2.C3H6O3
Molecular Weight 469.5053
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DROPERIDOL LACTATE

SMILES

CC(O)C(O)=O.FC1=CC=C(C=C1)C(=O)CCCN2CCC(=CC2)N3C(=O)NC4=CC=CC=C34

InChI

InChIKey=CUYSTLHETVVORS-UHFFFAOYSA-N
InChI=1S/C22H22FN3O2.C3H6O3/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;1-2(4)3(5)6/h1-2,4-5,7-11H,3,6,12-15H2,(H,24,28);2,4H,1H3,(H,5,6)

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/droperidol.html

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. 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. Droperidol is used to produce tranquilization and to reduce the incidence of nausea and vomiting in surgical and diagnostic procedures.

CNS Activity

Curator's Comment: Droperidol causes a CNS depression at subcortical levels of the brain, midbrain, and brainstem reticular formation.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
INAPSINE

Approved Use

Droperidol injection is indicated to reduce the incidence of nausea and vomiting associated with surgical and diagnostic procedures.

Launch Date

1970
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.5 μg/L
0.02 mg/kg single, nasal
dose: 0.02 mg/kg
route of administration: Nasal
experiment type: SINGLE
co-administered:
DROPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
26.6 μg/L
0.02 mg/kg single, intravenous
dose: 0.02 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DROPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
18.7 μg × h/L
0.02 mg/kg single, nasal
dose: 0.02 mg/kg
route of administration: Nasal
experiment type: SINGLE
co-administered:
DROPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
40 μg × h/L
0.02 mg/kg single, intravenous
dose: 0.02 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DROPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.4 h
0.02 mg/kg single, nasal
dose: 0.02 mg/kg
route of administration: Nasal
experiment type: SINGLE
co-administered:
DROPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.1 h
0.02 mg/kg single, intravenous
dose: 0.02 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DROPERIDOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.4 mg/kg multiple, oral
unhealthy, 2-9 years
Disc. AE: QT interval prolonged...
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Other AEs: Asthenia, Chills...
Other AEs:
Asthenia (24.6%)
Chills (3.3%)
Anorexia (3.3%)
Akathisia (16.4%)
Anxiety (27.9%)
Confusion (3.3%)
Dizziness (9.8%)
Dry mouth (9.8%)
Nervousness (4.9%)
Paresthesia (3.3%)
Somnolence (24.6%)
Tremor (1.6%)
Pharyngitis (4.9%)
Rhinitis (4.9%)
Sweaty (8.2%)
Sources:
2.5 mg multiple, intravenous (starting)
unhealthy
Disc. AE: Torsades de pointes...
AEs

AEs

AESignificanceDosePopulation
QT interval prolonged Disc. AE
0.4 mg/kg multiple, oral
unhealthy, 2-9 years
Tremor 1.6%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Akathisia 16.4%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Asthenia 24.6%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Somnolence 24.6%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Anxiety 27.9%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Anorexia 3.3%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Chills 3.3%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Confusion 3.3%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Paresthesia 3.3%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Nervousness 4.9%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Pharyngitis 4.9%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Rhinitis 4.9%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Sweaty 8.2%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Dizziness 9.8%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Dry mouth 9.8%
8.25 mg single, intramuscular
Highest studied dose
Dose: 8.25 mg
Route: intramuscular
Route: single
Dose: 8.25 mg
Sources:
unhealthy, 42 ± 10.0 years
n = 61
Health Status: unhealthy
Condition: acute migraine headache
Age Group: 42 ± 10.0 years
Sex: M+F
Population Size: 61
Sources:
Torsades de pointes Disc. AE
2.5 mg multiple, intravenous (starting)
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
[Postoperative nausea and vomiting--still a problem?].
2001
[The influence of age on hemodynamics and the dose requirements of propofol and buprenorphine in total intravenous anesthesia combined with continuous epidural anesthesia].
2001 Aug
Effects of dopamine antagonists in human eye accommodation.
2001 Feb
Suppression of potassium conductance by droperidol has influence on excitability of spinal sensory neurons.
2001 Feb
Prevention of postoperative nausea and vomiting with antiemetics in patients undergoing middle ear surgery: comparison of a small dose of propofol with droperidol or metoclopramide.
2001 Jan
[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo].
2001 Jul
Plasma glucocorticoid concentrations after fentanyl-droperidol, ketamine-xylazine and ketamine-diazepam anaesthesia in New Zealand white rabbits.
2001 Jun 23
Impact of antiemetic selection on postoperative nausea and vomiting and patient satisfaction.
2001 May
[Postoperative nausea--still a problem].
2001 Oct 3
Antipsychotic-related QTc prolongation, torsade de pointes and sudden death.
2002
Current practices in managing acutely disturbed patients at three hospitals in Rio de Janeiro-Brazil: a prevalence study.
2002
The black box warning.
2002 Fall
Four-step local anesthesia and sedation for thoracoscopic diagnosis and management of pleural diseases.
2002 Jun
[Effects of preincisional epidural administration of lidocaine and fentanyl on postoperative pain management following hysterectomy].
2002 Jun 10
Derivative spectrophotometric determination of droperidol in presence of parabens.
2002 Jun 20
Superior prolonged antiemetic prophylaxis with a four-drug multimodal regimen - comparison with propofol or placebo.
2002 Mar
Treatment patterns of isolated benign headache in US emergency departments.
2002 Mar
Black-box warning for droperidol surprises pharmacists.
2002 Mar 15
Using imprecise probabilities to address the questions of inference and decision in randomized clinical trials.
2002 May
Acute dystonia by droperidol during intravenous patient-controlled analgesia in young patients.
2002 Oct
Effects of anesthesia on efferent-mediated adaptation of the DPOAE.
2002 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Intravenous or Intramuscular
Dosage: The dosage should be individualized. Factors to be considered in determining dose are age, body weight, physical status, underlying pathological condition, use of other drugs, the type of anesthesia to be used, and the surgical procedure involved. Vital signs and ECG should be monitored closely. Maximum Dosage: The maximum recommended initial dose is 2.5 mg IM or slow IV. Additional 1.25 mg doses of droperidol may be administered to achieve the desired effect. The additional doses should be administered with caution and only if the potential benefit outweighs the potential risk.
Route of Administration: Intravenous
Droperidol (10(-7) M) caused vasodilator effect (approximately 20% of vasorelaxation compared with maximal vasorelaxation induced by papaverine [3 x 10(-4) M] in rat vascular smooth muscle cells.
Name Type Language
DROPERIDOL LACTATE
WHO-DD  
Common Name English
2-HYDROXYPROPANOIC ACID - 1-(1-(4-(4-FLUOROPHENYL)-4-OXOBUTYL)-1,2,3,6-TETRAHYDRO-4-PYRIDINYL)-1,3-DIHYDRO-2H-BENZIMIDAZOL-2-ONE (1:1)
Systematic Name English
1-(1-(3-(P-FLUOROBENZOYL)PROPYL)-1,2,3,6-TETRAHYDRO-4-PYRIDYL)-2-BENZIMIDAZOLINONE 2-HYDROXYPROPANOIC ACID
Systematic Name English
DROPERIDOL DL-LACTATE
Common Name English
Droperidol lactate [WHO-DD]
Common Name English
3-(1-(4-(4-FLUOROPHENYL)-4-OXOBUTYL)-3,6-DIHYDRO-2H-PYRIDIN-4-YL)-1H-BENZIMIDAZOL-2-ONE 2-HYDROXYPROPANOIC ACID
Systematic Name English
Code System Code Type Description
EVMPD
SUB01839MIG
Created by admin on Sat Dec 16 09:00:02 GMT 2023 , Edited by admin on Sat Dec 16 09:00:02 GMT 2023
PRIMARY
PUBCHEM
9956314
Created by admin on Sat Dec 16 09:00:02 GMT 2023 , Edited by admin on Sat Dec 16 09:00:02 GMT 2023
PRIMARY
FDA UNII
09NO5N37E0
Created by admin on Sat Dec 16 09:00:02 GMT 2023 , Edited by admin on Sat Dec 16 09:00:02 GMT 2023
PRIMARY
SMS_ID
100000087719
Created by admin on Sat Dec 16 09:00:02 GMT 2023 , Edited by admin on Sat Dec 16 09:00:02 GMT 2023
PRIMARY