Azaperone
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
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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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AD(3) dopamine receptor inhibitorHumans AD(2) dopamine receptor inhibitorHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Azaperone is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Azaperone. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Azaperone. Agomelatine The risk or severity of CNS depression can be increased when Agomelatine is combined with Azaperone. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Azaperone. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Stresnil
Categories
- Drug Categories
- Antipsychotic Agents
- Antipsychotic Agents (First Generation [Typical])
- Butyrophenones
- Central Nervous System Agents
- Central Nervous System Depressants
- Dopamine Agents
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Hypnotics and Sedatives
- Ketones
- Neurotoxic agents
- Neurotransmitter Agents
- Psychotropic Drugs
- Tranquilizing Agents
- 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
- 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]
- Gerbig T: [Azaperone (Stresnil) as a sedative for dogs]. Berl Munch Tierarztl Wochenschr. 1979 Jan 1;92(1):12-5. [Article]
- Borka L, Valdimarsdottir S: The polymorphism of azaperone and clotrimazole. Acta Pharm Suec. 1975;12(5-6):479-84. [Article]
- Lang E: [Use of azaperone on the pig]. Berl Munch Tierarztl Wochenschr. 1970 Apr 15;83(8):141-3. [Article]
- Allsup FC, Hillidge CJ, Lees P, Serrano L: Azaperone-metomidate anaesthesia in the horse. Vet Rec. 1973 Nov 3;93(18):498. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Serrano L, Lees P: The applied pharmacology of azaperone in ponies. Res Vet Sci. 1976 May;20(3):316-23. [Article]
- External Links
- KEGG Drug
- D02620
- ChemSpider
- 14695
- BindingDB
- 50036733
- 2601502
- ChEBI
- 88301
- ChEMBL
- CHEMBL340211
- ZINC
- ZINC000002596977
- Wikipedia
- Azaperone
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Treatment Anxiety 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intramuscular - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.23 mg/mL ALOGPS logP 2.73 ALOGPS logP 3.21 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 16.4 Chemaxon pKa (Strongest Basic) 7.16 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 36.44 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 94.27 m3·mol-1 Chemaxon Polarizability 36.19 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 173.76004 predictedDeepCCS 1.0 (2019) [M+H]+ 176.11804 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.2112 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
1. DetailsD(3) dopamine receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation
- Specific Function
- dopamine neurotransmitter receptor activity, coupled via Gi/Go
- Gene Name
- DRD3
- Uniprot ID
- P35462
- Uniprot Name
- D(3) dopamine receptor
- Molecular Weight
- 44194.315 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsD(2) dopamine receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (PubMed:21645528). Positively regulates postnatal regression of retinal hyaloid vessels via suppression of VEGFR2/KDR activity, downstream of OPN5 (By similarity)
- Specific Function
- dopamine binding
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at February 25, 2016 18:15 / Updated at August 26, 2024 19:22