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
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
Coronary artery reperfusion: The ADP receptor P2Y(1) mediates early reactive hyperemia in vivo in pigs.
2004 Dec
Development of a rapid screening test for veterinary sedatives and the beta-blocker carazolol in porcine kidney by ELISA.
2004 Feb
Placentation in the paca (Agouti paca L).
2005 Feb 28
Use of buspirone and enrichment to manage aberrant behavior in an American badger (Taxidea taxus).
2005 Sep
Physiological routes from intra-uterine seminal contents to advancement of ovulation.
2006 Aug 3
Euthanasia of exotic pigs.
2006 Jul 8
Gelatinases, endonuclease and Vascular Endothelial Growth Factor during development and regression of swine luteal tissue.
2006 Nov 30
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
Bioavailability of heme iron in biscuit filling using piglets as an animal model for humans.
2008 Feb 18
Immobilization of black bears (Ursus americanus) with a combination of butorphanol, azaperone, and medetomidine.
2008 Jul
A novel method for transuterine identification of piglets.
2008 Jul
Comprehensive screening and quantification of veterinary drugs in milk using UPLC-ToF-MS.
2008 Jul
Thermal, cardiorespiratory and cortisol responses of impala (Aepyceros melampus) to chemical immobilisation with 4 different drug combinations.
2008 Sep
Resource efficiency and economic implications of alternatives to surgical castration without anaesthesia.
2009 Nov
Haloperidol and azaperone in drive-net captured Southern chamois (Rupicapra pyrenaica).
2010 Jul
Increasing abdominal pressure with and without PEEP: effects on intra-peritoneal, intra-organ and intra-vascular pressures.
2010 Jul 4
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
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
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WHO-VATC QN05AD90
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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
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PRIMARY
CAS
1649-18-9
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DRUG BANK
DB11376
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DAILYMED
19BV78AK7W
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RXCUI
2601502
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CHEBI
88301
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MESH
D001376
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MERCK INDEX
m2161
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FDA UNII
19BV78AK7W
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EVMPD
SUB05636MIG
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RS_ITEM_NUM
1045756
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NSC
170976
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PUBCHEM
15443
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WIKIPEDIA
Azaperone
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ECHA (EC/EINECS)
216-715-8
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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
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EPA CompTox
DTXSID2045361
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SMS_ID
100000086911
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ChEMBL
CHEMBL340211
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