Azaperone

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

Identification

Name
Azaperone
Accession Number
DB11376
Type
Small Molecule
Groups
Investigational, Vet approved
Description

Azaperone is a pyridinylpiperazine and butyrophenone neuroleptic drug with sedative and antiemetic effects, which is used mainly as a tranquilizer in veterinary medicine. It is used mainly in pigs and elephants. More rarely it may be used in humans as an antipsychotic drug, but this is uncommon. Use in horses is avoided as adverse reactions may occur.

Structure
Thumb
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
  • Azaperonum
  • NSC 170976
  • Stresnil
External IDs
NSC-170976 / R 1929 / R-1929
Categories
UNII
19BV78AK7W
CAS number
1649-18-9
Weight
Average: 327.403
Monoisotopic: 327.174690503
Chemical Formula
C19H22FN3O
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineAzaperone may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Azaperone is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineAzaperone may decrease the stimulatory activities of 3,4-Methylenedioxyamphetamine.
3,5-DinitrocatecholThe therapeutic efficacy of 3,5-Dinitrocatechol can be decreased when used in combination with Azaperone.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Azaperone.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Azaperone.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Azaperone is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Azaperone.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Azaperone.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Azaperone.
Food Interactions
Not Available

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. [PubMed:925952]
  2. Gerbig T: [Azaperone (Stresnil) as a sedative for dogs]. Berl Munch Tierarztl Wochenschr. 1979 Jan 1;92(1):12-5. [PubMed:420685]
  3. Borka L, Valdimarsdottir S: The polymorphism of azaperone and clotrimazole. Acta Pharm Suec. 1975;12(5-6):479-84. [PubMed:1217501]
  4. Lang E: [Use of azaperone on the pig]. Berl Munch Tierarztl Wochenschr. 1970 Apr 15;83(8):141-3. [PubMed:5519354]
  5. Allsup FC, Hillidge CJ, Lees P, Serrano L: Azaperone-metomidate anaesthesia in the horse. Vet Rec. 1973 Nov 3;93(18):498. [PubMed:4786114]
  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. [PubMed:3411917]
  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. [PubMed:19239653]
  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. [PubMed:3322780]
  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. [PubMed:19395755]
  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. [PubMed:10982132]
  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. [PubMed:12398308]
  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. [PubMed:17186408]
  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. [PubMed:17386737]
  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. [PubMed:17929705]
  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. [PubMed:17939346]
  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. [PubMed:18689666]
  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. [PubMed:18817017]
  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. [PubMed:19111512]
  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. [PubMed:19395756]
  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. [PubMed:19579764]
  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. [PubMed:20006891]
  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. [PubMed:21210371]
  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. [PubMed:22287670]
  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. [PubMed:23140663]
  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. [PubMed:24490337]
  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. [PubMed:24712163]
  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. [PubMed:24807358]
  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. [PubMed:25105814]
  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. [PubMed:25655411]
  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. [PubMed:26056882]
  31. Serrano L, Lees P: The applied pharmacology of azaperone in ponies. Res Vet Sci. 1976 May;20(3):316-23. [PubMed:935668]
External Links
KEGG Drug
D02620
ChemSpider
14695
BindingDB
50036733
ChEBI
88301
ChEMBL
CHEMBL340211
Wikipedia
Azaperone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentFeeling Anxious1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-3900000000-2b80dd893322c22b1ec2

Taxonomy

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
Alkyl-phenylketone / Pyridinylpiperazine / N-arylpiperazine / Butyrophenone / Phenylbutylamine / Benzoyl / Dialkylarylamine / Aryl alkyl ketone / Aminopyridine / Fluorobenzene
show 25 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on February 25, 2016 11:15 / Updated on November 02, 2018 07:09