Azaperone
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Basic Info
| Common Name | Azaperone(F05999) |
| 2D Structure | |
| FRCD ID | F05999 |
| CAS Number | 1649-18-9 |
| PubChem CID | 15443 |
| Formula | C19H22FN3O |
| IUPAC Name | 1-(4-fluorophenyl)-4-(4-pyridin-2-ylpiperazin-1-yl)butan-1-one |
| 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 |
| Canonical SMILES | C1CN(CCN1CCCC(=O)C2=CC=C(C=C2)F)C3=CC=CC=N3 |
| Isomeric SMILES | C1CN(CCN1CCCC(=O)C2=CC=C(C=C2)F)C3=CC=CC=N3 |
| Synonyms |
Azaperone
1649-18-9
Stresnil
Fluoperidol
Suicalm
Azaperon
Azeperone
Eucalmyl
Sedaperone vet
Azaperona
|
| Classifies |
Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbonyl compounds |
| Intermediate Tree Nodes | Ketones - Aryl ketones - Phenylketones |
| Direct Parent | Alkyl-phenylketones |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Alkyl-phenylketone - Pyridinylpiperazine - N-arylpiperazine - Butyrophenone - Phenylbutylamine - Benzoyl - Dialkylarylamine - Aryl alkyl ketone - Aminopyridine - Fluorobenzene - Halobenzene - N-alkylpiperazine - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - 1,4-diazinane - Gamma-aminoketone - Piperazine - Pyridine - Imidolactam - Benzenoid - Heteroaromatic compound - Tertiary amine - Tertiary aliphatic amine - Azacycle - Organoheterocyclic compound - Organofluoride - Organohalogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Organopnictogen compound - Organic oxide - Amine - Aromatic heteromonocyclic compound |
| 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 327.403 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 6 |
| Complexity | 390 |
| Monoisotopic Mass | 327.175 |
| Exact Mass | 327.175 |
| XLogP | 3.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9814 |
| Human Intestinal Absorption | HIA+ | 0.9862 |
| Caco-2 Permeability | Caco2- | 0.5087 |
| P-glycoprotein Substrate | Substrate | 0.6315 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6518 |
| Inhibitor | 0.5991 | |
| Renal Organic Cation Transporter | Inhibitor | 0.6706 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6973 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8848 |
| CYP450 2D6 Substrate | Non-substrate | 0.5000 |
| CYP450 3A4 Substrate | Non-substrate | 0.5714 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8906 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.6520 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8377 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5372 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8033 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.9223 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Strong inhibitor | 0.5443 |
| Inhibitor | 0.8653 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8876 |
| Fish Toxicity | Low FHMT | 0.6224 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9775 |
| Honey Bee Toxicity | Low HBT | 0.9229 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | II | 0.7458 |
| Carcinogenicity (Three-class) | Non-required | 0.5637 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.3679 | LogS |
| Caco-2 Permeability | 1.0314 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.0949 | LD50, mol/kg |
| Fish Toxicity | 1.5764 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8039 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Pig,Edible Offal | Japan | 0.01ppm | |||
| Pig,Kidney | Japan | 0.1ppm | |||
| Pig,Liver | Japan | 0.1ppm | |||
| Pig,Fat | Japan | 0.06ppm | |||
| Pig,Muscle | Japan | 0.06ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Simultaneous determination of azaperone and azaperol in animal tissues by HPLCwith confirmation by electrospray ionization mass spectrometry. | J Chromatogr B Analyt Technol Biomed Life Sci | 2009 Jan 15 | 19111512 |
| Estimating provisional acceptable residues for extralabel drug use in livestock. | Regul Toxicol Pharmacol | 1999 Jun | 10388614 |
| Confirmation of azaperone and its metabolically reduced form, azaperol, in swine liver by gas chromatography/mass spectrometry. | J AOAC Int | 1999 Jul-Aug | 10444823 |
| Multi-residue analysis of tranquillizers in meat: confirmatory assays using mass spectrometry. | Analyst | 1998 Dec | 10435288 |
| [Ban of the use of metomidate (Hypnodil) in swine. Background, consequences andalternatives]. | Tierarztl Prax Ausg G Grosstiere Nutztiere | 1997 Aug | 9441044 |