U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H22FN3O
Molecular Weight 327.3959
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZAPERONE

SMILES

FC1=CC=C(C=C1)C(=O)CCCN2CCN(CC2)C3=CC=CC=N3

InChI

InChIKey=XTKDAFGWCDAMPY-UHFFFAOYSA-N
InChI=1S/C19H22FN3O/c20-17-8-6-16(7-9-17)18(24)4-3-11-22-12-14-23(15-13-22)19-5-1-2-10-21-19/h1-2,5-10H,3-4,11-15H2

HIDE SMILES / InChI

Molecular Formula C19H22FN3O
Molecular Weight 327.3959
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Azaperone (Stresnil, Fluoperidol) is a pyridinylpiperazine and butyrophenone neuroleptic drug with sedative and antiemetic effects. It is mainly as a tranquilizer in veterinary medicine. Azaperone is officially indicated for the “control of aggressiveness when mixing or regrouping weanling or feeder pigs weighing up to 36.4 kg”. It is also used clinically as a general tranquilizer for swine, in particular with aggressive sows to allow piglets to be accepted, and as a preoperative agent prior to general anesthesia or cesarian section with local anesthesia. Azaperone has also been used as a neuroleptic in horses, but some horses develop adverse reactions (sweating, muscle tremors, panic reaction, CNS excitement) and IV administration has resulted in significant arterial hypotension in the horse; because of these effects, most clinicians avoid the use of this drug in equines. Azaperone appears to have minimal effects on respiration and may inhibit some of the respiratory depressant actions of general anesthetics. A slight reduction of arterial blood pressure has been measured in pigs after IM injections of azaperone, which is apparently due to slight alpha-adrenergic blockade. Azaperone has been demonstrated to prevent the development of halothane-induced malignant hyperthermia in susceptible pigs. Preliminary studies have suggested that the effects of butyrephenones may be antagonized by 4-aminopyridine. Azaperone acts primarily as a dopamine antagonist but also has some antihistaminic and anticholinergic properties as seen with similar drugs such as haloperidol. Azaperone may cause hypotension and while it has minimal effects on respiration in pigs, high doses in humans can cause respiratory depression which may be why it is rarely used in humans. Higher doses are used for anesthesia in combination with other drugs such as xylazine, tiletamine and zolazepam. Azaperone is also used in combination with strong narcotics such as etorphine or carfentanil for tranquilizing large animals such as elephants.

CNS Activity

Curator's Comment: Azaperone is thought to act on CNS to make animals indifferent to their surrounding environment

Originator

Curator's Comment: # Janssen Pharmaceutica laboratories

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
STRESNIL

Approved Use

Unknown

Launch Date

2012
PubMed

PubMed

TitleDatePubMed
Chemical anesthesia of northern sea otters (Enhydra lutris): results of past field studies.
2001 Jun
Optimization of intraperitoneal injection anesthesia in mice: drugs, dosages, adverse effects, and anesthesia depth.
2001 Oct
A review of drugs and techniques used for sedation and anaesthesia in captive rhinoceros species.
2004 Sep
Successful treatment of a squamous cell carcinoma in a white rhinoceros, Ceratotherium simum.
2007 Dec
Evaluation of the effects of the sedation with azaperone/acepromazine and immobilization with guaiphenesin/thiopentone in mules.
2007 Feb
Mild hypothermia reduces cardiac post-ischemic reactive hyperemia.
2007 Feb 26
Anaesthesia for castration of piglets: comparison between intranasal and intramuscular application of ketamine, climazolam and azaperone.
2007 Sep
Alveolar recruitment can be predicted from airway pressure-lung volume loops: an experimental study in a porcine acute lung injury model.
2008
Bioavailability of heme iron in biscuit filling using piglets as an animal model for humans.
2008 Feb 18
Thermal, cardiorespiratory and cortisol responses of impala (Aepyceros melampus) to chemical immobilisation with 4 different drug combinations.
2008 Sep
[Determination of azaperone and carazolol residues in animals kidney using LC-MS/MS method].
2009
Butorphanol, azaperone, and medetomidine anesthesia in free-ranging white-tailed deer (Odocoileus virginianus) using radiotransmitter darts.
2009 Apr
Butorphanol-azaperone-medetomidine for immobilization of captive white-tailed deer.
2009 Apr
Rapid method for the determination of tranquilizers and a beta-blocker in porcine and bovine kidney by liquid chromatography with tandem mass spectrometry.
2009 Apr 1
Computer tomographic investigation of subcutaneous adipose tissue as an indicator of body composition.
2009 Jul 1
Resource efficiency and economic implications of alternatives to surgical castration without anaesthesia.
2009 Nov
Different solutions used for submucosal injection influenced early healing of gastric endoscopic mucosal resection in a preclinical study in experimental pigs.
2009 Sep
Psychological interventions in the management of common skin conditions.
2010
Anti- or profibrillatory effects of Na(+) channel blockade depend on the site of application relative to gradients in repolarization.
2010
Standardized intensive care unit management in an anhepatic pig model: new standards for analyzing liver support systems.
2010
Postmortem Evaluation of Left Flank Laparoscopic Access in an Adult Female Giraffe (Giraffa camelopardalis).
2010
Holmium-166 poly(L-lactic acid) microsphere radioembolisation of the liver: technical aspects studied in a large animal model.
2010 Apr
Granuloma encapsulation is a key factor for containing tuberculosis infection in minipigs.
2010 Apr 6
The use of in vitro technologies coupled with high resolution accurate mass LC-MS for studying drug metabolism in equine drug surveillance.
2010 Jan
Acid-base balance and ventilation during sternal and lateral recumbency in field immobilized black rhinoceros (Diceros bicornis) receiving oxygen insufflation: a preliminary report.
2010 Jan
Apyrase treatment of myocardial infarction according to a clinically applicable protocol fails to reduce myocardial injury in a porcine model.
2010 Jan 4
Haloperidol and azaperone in drive-net captured Southern chamois (Rupicapra pyrenaica).
2010 Jul
Enhanced blood pressure and appetite responses to chronic central melanocortin-3/4 receptor blockade in dietary-induced obesity.
2010 Jul
Increasing abdominal pressure with and without PEEP: effects on intra-peritoneal, intra-organ and intra-vascular pressures.
2010 Jul 4
Preclinical electrogastrography in experimental pigs.
2010 Jun
Use of haloperidol and azaperone for stress control in roe deer (Capreolus capreolus) captured by means of drive-nets.
2010 Jun
Low plasma potassium in deep hypothermic cardiac arrest indicates that cardiac arrest is secondary to hypothermia: a porcine study.
2010 Jun
Multidetector row computed tomography evaluation of the micropig kidney as a potential renal donor.
2010 Mar
Minimum alveolar concentrations and hemodynamic effects of two different preparations of sevoflurane in pigs.
2010 May
Prothrombin complex concentrate mitigates diffuse bleeding after cardiopulmonary bypass in a porcine model.
2010 Nov
64-channel multi-detector row CT angiographic evaluation of the micropigs for potential living donor lung transplantation.
2010 Sep
Patents

Sample Use Guides

Swine: a) For approved indication of mixing feeder or weanling pigs: 2.2 mg/kg deeply IM' b) Preanesthetic: 2 - 4 mg/kg IM; Immobilizing agent: 5.3 - 8 mg/kg IM; c) Sedation: 1 mg/kg IM; Reduction of aggressiveness: 2.5 mg/kg IM; Total dose of azaperone for adult Asian captive elephants 80-100 mg; up to 140 mg for a large elephant. Induction in 20-30 minutes; duration 45-60 minutes Knock-down or immobilant: 5 - 10 mg/kg IM
Route of Administration: Intramuscular
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:51:00 GMT 2023
Edited
by admin
on Sat Dec 16 15:51:00 GMT 2023
Record UNII
19BV78AK7W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZAPERONE
GREEN BOOK   INN   MART.   MI   USAN   USP   USP-RS  
INN   USAN  
Official Name English
AZAPERONE [GREEN BOOK]
Common Name English
4'-FLUORO-4-(4-(2-PYRIDYL)-1-PIPERAZINYL)BUTYROPHENONE
Systematic Name English
AZAPERONE [MI]
Common Name English
azaperone [INN]
Common Name English
AZAPERONE FOR VETERINARY USE
EP  
Common Name English
R 1929
Code English
1-BUTANONE, 1-(4-FLUOROPHENYL)-4-(4-(2-PYRIDINYL)-1-PIPERAZINYL)-
Systematic Name English
R-1929
Code English
AZAPERONE [USAN]
Common Name English
AZAPERONE [MART.]
Common Name English
NSC-170976
Code English
AZAPERONE [USP-RS]
Common Name English
AZAPERONE [USP MONOGRAPH]
Common Name English
AZAPERONE [USP IMPURITY]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
WHO-VATC QN01AX91
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
WHO-VATC QN05AD90
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
CFR 21 CFR 522.150
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
Code System Code Type Description
INN
2331
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
CAS
1649-18-9
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
DRUG BANK
DB11376
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
DAILYMED
19BV78AK7W
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
RXCUI
2601502
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PRIMARY
CHEBI
88301
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
MESH
D001376
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PRIMARY
MERCK INDEX
m2161
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY Merck Index
FDA UNII
19BV78AK7W
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
EVMPD
SUB05636MIG
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
RS_ITEM_NUM
1045756
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PRIMARY
NSC
170976
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PRIMARY
PUBCHEM
15443
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
WIKIPEDIA
Azaperone
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
216-715-8
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
NCI_THESAURUS
C74187
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID2045361
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
SMS_ID
100000086911
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
ChEMBL
CHEMBL340211
Created by admin on Sat Dec 16 15:51:00 GMT 2023 , Edited by admin on Sat Dec 16 15:51:00 GMT 2023
PRIMARY
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BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
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BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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