Azaperone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Azaperone
DrugBank Accession Number
DB11376
Background

Azaperone is a pyridinylpiperazine and butyrophenone agent that is capable of eliciting neuroleptic sedative and antiemetic effects. It is subsequently employed predominantly as a veterinary tranquilizer and mainly for pigs and elephants. At the same time, the agent generally does not see equine use as particular adverse reactions may happen. More rarely it may be used in humans as an antipsychotic drug, but this is uncommon.

Type
Small Molecule
Groups
Investigational, Vet approved
Structure
Weight
Average: 327.403
Monoisotopic: 327.174690503
Chemical Formula
C19H22FN3O
Synonyms
  • 1-(3-(4-Fluorobenzoyl)propyl)-4-(2-pyridyl)piperazine
  • 1-(4-Fluorophenyl)-4-[4-(2-pyridinyl)-1-piperazinyl]-1-butanone
  • 4'-Fluoro-4-(4-(2-pyridyl)-1-piperazinyl)butyrophenone
  • Azaperon
  • Azaperona
  • Azaperone
  • Azaperonum
External IDs
  • NSC-170976
  • R 1929
  • R-1929

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Azaperone is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Azaperone.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Azaperone.
AgomelatineThe risk or severity of CNS depression can be increased when Agomelatine is combined with Azaperone.
AlfentanilThe risk or severity of CNS depression can be increased when Alfentanil is combined with Azaperone.
Food Interactions
Not Available

Products

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International/Other Brands
Stresnil

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Alkyl-phenylketones
Alternative Parents
Pyridinylpiperazines / N-arylpiperazines / Phenylbutylamines / Butyrophenones / Aryl alkyl ketones / Dialkylarylamines / Benzoyl derivatives / Aminopyridines and derivatives / N-alkylpiperazines / Fluorobenzenes
show 10 more
Substituents
1,4-diazinane / Alkyl-phenylketone / Amine / Aminopyridine / Aromatic heteromonocyclic compound / Aryl alkyl ketone / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
19BV78AK7W
CAS number
1649-18-9
InChI Key
XTKDAFGWCDAMPY-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(4-fluorophenyl)-4-[4-(pyridin-2-yl)piperazin-1-yl]butan-1-one
SMILES
FC1=CC=C(C=C1)C(=O)CCCN1CCN(CC1)C1=CC=CC=N1

References

General References
  1. Baeyens W, De Moerloose P, De Taeye L: Fluorescence characteristics of azaperone and of an azaperone mononitrogen oxide. J Pharm Sci. 1977 Dec;66(12):1787-9. [Article]
  2. Gerbig T: [Azaperone (Stresnil) as a sedative for dogs]. Berl Munch Tierarztl Wochenschr. 1979 Jan 1;92(1):12-5. [Article]
  3. Borka L, Valdimarsdottir S: The polymorphism of azaperone and clotrimazole. Acta Pharm Suec. 1975;12(5-6):479-84. [Article]
  4. Lang E: [Use of azaperone on the pig]. Berl Munch Tierarztl Wochenschr. 1970 Apr 15;83(8):141-3. [Article]
  5. Allsup FC, Hillidge CJ, Lees P, Serrano L: Azaperone-metomidate anaesthesia in the horse. Vet Rec. 1973 Nov 3;93(18):498. [Article]
  6. Olson ME, Renchko P: Azaperone and azaperone-ketamine as a neuroleptic sedative and anesthetic in rats and mice. Lab Anim Sci. 1988 Jun;38(3):299-304. [Article]
  7. Heinonen ML, Raekallio MR, Oliviero C, Ahokas S, Peltoniemi OA: Comparison of azaperone-detomidine-butorphanol-ketamine and azaperone-tiletamine-zolazepam for anaesthesia in piglets. Vet Anaesth Analg. 2009 Mar;36(2):151-7. doi: 10.1111/j.1467-2995.2008.00443.x. [Article]
  8. Duverger-van Bogaert M, Vanparys P, de Meester C, Marsboom R: Mutagenicity evaluation of azaperone in the Salmonella/microsome test. Drug Chem Toxicol. 1987;10(3-4):329-38. [Article]
  9. Miller BF, Osborn DA, Lance WR, Howze MB, Warren RJ, Miller KV: Butorphanol-azaperone-medetomidine for immobilization of captive white-tailed deer. J Wildl Dis. 2009 Apr;45(2):457-67. [Article]
  10. Radcliffe RW, Ferrell ST, Childs SE: Butorphanol and azaperone as a safe alternative for repeated chemical restraint in captive white rhinoceros (Ceratotherium simum). J Zoo Wildl Med. 2000 Jun;31(2):196-200. [Article]
  11. Read MR, McCorkell RB: Use of azaperone and zuclopenthixol acetate to facilitate translocation of white-tailed deer (Odocoileus virginianus). J Zoo Wildl Med. 2002 Jun;33(2):163-5. [Article]
  12. Carmona JU, Giraldo CE, Aristizabal W, Garcia A, Vallejo LG: Evaluation of the effects of the sedation with azaperone/acepromazine and immobilization with guaiphenesin/thiopentone in mules. Vet Res Commun. 2007 Feb;31(2):125-32. Epub 2006 Dec 20. [Article]
  13. Cerkvenik-Flajs V: Determination of residues of azaperone in the kidneys by liquid chromatography with fluorescence detection. Anal Chim Acta. 2007 Mar 14;586(1-2):374-82. Epub 2006 Nov 10. [Article]
  14. Axiak SM, Jaggin N, Wenger S, Doherr MG, Schatzmann U: Anaesthesia for castration of piglets: comparison between intranasal and intramuscular application of ketamine, climazolam and azaperone. Schweiz Arch Tierheilkd. 2007 Sep;149(9):395-402. [Article]
  15. Wenger S, Boardman W, Buss P, Govender D, Foggin C: The cardiopulmonary effects of etorphine, azaperone, detomidine, and butorphanol in field-anesthetized white rhinoceroses (Ceratotherium simum). J Zoo Wildl Med. 2007 Sep;38(3):380-7. [Article]
  16. Wolfe LL, Goshorn CT, Baruch-Mordo S: Immobilization of black bears (Ursus americanus) with a combination of butorphanol, azaperone, and medetomidine. J Wildl Dis. 2008 Jul;44(3):748-52. [Article]
  17. Mich PM, Wolfe LL, Sirochman TM, Sirochman MA, Davis TR, Lance WR, Miller MW: Evaluation of intramuscular butorphanol, azaperone, and medetomidine and nasal oxygen insufflation for the chemical immobilization of white-tailed deer, Odocoileus virginianus. J Zoo Wildl Med. 2008 Sep;39(3):480-7. [Article]
  18. Aoki Y, Hakamata H, Igarashi Y, Uchida K, Kobayashi H, Hirayama N, Kotani A, Kusu F: Simultaneous determination of azaperone and azaperol in animal tissues by HPLC with confirmation by electrospray ionization mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jan 15;877(3):166-72. doi: 10.1016/j.jchromb.2008.11.047. Epub 2008 Dec 7. [Article]
  19. Siegal-Willott J, Citino SB, Wade S, Elder L, Hayek LA, Lance WR: Butorphanol, azaperone, and medetomidine anesthesia in free-ranging white-tailed deer (Odocoileus virginianus) using radiotransmitter darts. J Wildl Dis. 2009 Apr;45(2):468-80. [Article]
  20. Zawadzka I, Rodziewicz L: [Determination of azaperone and carazolol residues in animals kidney using LC-MS/MS method]. Rocz Panstw Zakl Hig. 2009;60(1):19-23. [Article]
  21. Mentaberre G, Lopez-Olvera JR, Casas-Diaz E, Bach-Raich E, Marco I, Lavin S: Use of haloperidol and azaperone for stress control in roe deer (Capreolus capreolus) captured by means of drive-nets. Res Vet Sci. 2010 Jun;88(3):531-5. doi: 10.1016/j.rvsc.2009.11.001. Epub 2009 Dec 14. [Article]
  22. Nussbaumer I, Indermuhle N, Zimmermann W, Leist Y: [Piglet castration using injection anesthesia: experiences with a combination of azaperone, butorphanol and ketamine]. Schweiz Arch Tierheilkd. 2011 Jan;153(1):33-5. doi: 10.1024/0036-7281/a000140. [Article]
  23. Ruediger K, Schulze M: Post-farrowing stress management in sows by administration of azaperone: effects on piglets performance. J Anim Sci. 2012 Jul;90(7):2331-6. doi: 10.2527/jas.2011-4661. Epub 2012 Jan 27. [Article]
  24. McCormick AV, Wheeler JM, Guthrie CR, Liachko NF, Kraemer BC: Dopamine D2 receptor antagonism suppresses tau aggregation and neurotoxicity. Biol Psychiatry. 2013 Mar 1;73(5):464-71. doi: 10.1016/j.biopsych.2012.08.027. Epub 2012 Nov 7. [Article]
  25. Lahrmann KH, Baars J, Rintisch U: [Perioperative intensive-medical investigations regarding compatibility of the ketamine-azaperone-general anesthesia in pigs]. Berl Munch Tierarztl Wochenschr. 2014 Jan-Feb;127(1-2):3-11. [Article]
  26. Bapodra P, Cracknell J, Wolfe BA: Comparison of butorphanol-detomidine versus butorphanol-azaperone for the standing sedation of captive greater one-horned rhinoceroses (Rhinoceros unicornis). J Zoo Wildl Med. 2014 Mar;45(1):60-8. [Article]
  27. Wolfe LL, Fisher MC, Davis TR, Miller MW: Efficacy of a low-dosage combination of butorphanol, azaperone, and medetomidine (BAM) to immobilize Rocky Mountain elk. J Wildl Dis. 2014 Jul;50(3):676-80. doi: 10.7589/2014-02-026. Epub 2014 May 7. [Article]
  28. Boardman WS, Caraguel CG, Raath JP, Van Zijll Langhout M: Intravenous butorphanol improves cardiopulmonary parameters in game-ranched white rhinoceroses (Ceratotherium simum) immobilized with etorphine and azaperone. J Wildl Dis. 2014 Oct;50(4):849-57. doi: 10.7589/2013-12-327. Epub 2014 Aug 8. [Article]
  29. Szabo Z, Venter DJ, Luyt Edu C, Raath C: The use of thiafentanil oxalate and azaperone for reversible immobilisation of African buffalo (Syncerus caffer) within a nature reserve - Short communication. Acta Vet Hung. 2015 Mar;63(1):11-5. doi: 10.1556/AVet.2015.002. [Article]
  30. Lapid R, Shilo-Benjamini Y: IMMOBILIZATION OF CAPTIVE NUBIAN IBEX (CAPRA NUBIANA) WITH BUTORPHANOL-MIDAZOLAM-MEDETOMIDINE OR BUTORPHANOL-AZAPERONE-MEDETOMIDINE AND ATIPAMEZOLE REVERSAL. J Zoo Wildl Med. 2015 Jun;46(2):291-7. doi: 10.1638/2014-0202R1.1. [Article]
  31. Serrano L, Lees P: The applied pharmacology of azaperone in ponies. Res Vet Sci. 1976 May;20(3):316-23. [Article]
KEGG Drug
D02620
ChemSpider
14695
BindingDB
50036733
RxNav
2601502
ChEBI
88301
ChEMBL
CHEMBL340211
ZINC
ZINC000002596977
Wikipedia
Azaperone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAnxiety1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntramuscular
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.23 mg/mLALOGPS
logP2.73ALOGPS
logP3.21Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)16.4Chemaxon
pKa (Strongest Basic)7.16Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area36.44 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity94.27 m3·mol-1Chemaxon
Polarizability36.19 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00di-3900000000-2b80dd893322c22b1ec2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-3900000000-2b80dd893322c22b1ec2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-016r-0907000000-963cbc73ced76fab0314
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xs-0902000000-a23d28cd87a488aa6f90
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-0019000000-8a57086abd281d807ec8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f92-1195000000-8425c2e9454ae484b217
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-0911000000-b01348c6fd1cf4dce1f9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-4792000000-e80a482dbabc625f1f00
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-173.76004
predicted
DeepCCS 1.0 (2019)
[M+H]+176.11804
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.2112
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:15 / Updated at February 21, 2021 18:53