Acepromazine

Common Name

Acepromazine Description

Acepromazine is only found in individuals that have used or taken this drug. It is one of the phenothiazine derivative psychotropic drugs, used little in humans, however frequently in animals as a sedative and antiemetic.Acepromazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 – different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejacliation difficlities), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism – controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficlity/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects). Structure

Synonyms

Value Source 1-[10-(3-dimethylamino-PROPYL)-10H-phenothiazin-2-yl]-ethanoneChEBI 10-(3-Dimethylaminopropyl)phenothiazin-3-yl methyl ketoneChEBI 10-(3-Dimethylaminopropyl)phenothiazine-3-ethyloneChEBI AcetazineChEBI AcetopromazineChEBI AcetylpromazineChEBI CalmivetMeSH Sanofi brand OF acepromazine maleateMeSH Seid brand OF acepromazine maleateMeSH VetranquilMeSH Acepromazine maleateMeSH Maleate, acepromazineMeSH PlegicilMeSH Vétoquinol brand OF acepromazine maleateMeSH

Chemical Formlia

C19H22N2OS Average Molecliar Weight

326.456 Monoisotopic Molecliar Weight

326.145284026 IUPAC Name

1-{10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl}ethan-1-one Traditional Name

Ace CAS Registry Number

61-00-7 SMILES

CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(C=C2)C(C)=O

InChI Identifier

InChI=1S/C19H22N2OS/c1-14(22)15-9-10-19-17(13-15)21(12-6-11-20(2)3)16-7-4-5-8-18(16)23-19/h4-5,7-10,13H,6,11-12H2,1-3H3

InChI Key

NOSIYYJFMPDDSA-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Benzothiazines Direct Parent

Phenothiazines Alternative Parents

  • Alkyldiarylamines
  • Diarylthioethers
  • Acetophenones
  • Aryl alkyl ketones
  • 1,4-thiazines
  • Trialkylamines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Substituents

  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Acetophenone
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Aryl alkyl ketone
  • Aryl ketone
  • Para-thiazine
  • Benzenoid
  • Ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
  • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • phenothiazines (CHEBI:44932 )
  • tertiary amino compound (CHEBI:44932 )
  • methyl ketone (CHEBI:44932 )
  • aromatic ketone (CHEBI:44932 )
  • Ontology Status

    Expected but not Quantified Origin

  • Drug
  • Biofunction

  • Antipsychotic Agents
  • Dopamine Antagonists
  • Sedatives and Hypnotics
  • Application

  • Pharmaceutical
  • Cellliar locations

  • Extracellliar
  • Membrane
  • Physical Properties State

    Liquid Experimental Properties

    Property Value Reference Melting Point< 25 °CNot Available Boiling PointNot AvailableNot Available Water Solubility9.80e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0098 mg/mLALOGPS logP4.32ALOGPS logP3.49ChemAxon logS-4.5ALOGPS pKa (Strongest Acidic)16.06ChemAxon pKa (Strongest Basic)8.5ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area23.55 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity99.35 m3·mol-1ChemAxon Polarizability37.17 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-004i-0009000000-ba8f0be449800ec10cf1View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-002r-9025000000-028fcf239ba77c5d26d0View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-000i-9060000000-33b3210f75c9aa6899f3View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0abi-9180000000-9b10f7d22435e199c283View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-9670000000-0c65cbf1672ae4899236View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane
  • Biofluid Locations

  • Blood
  • Urine
  • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01614

  • 21059682
  • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01614

  • 21059682
  • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01614 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    5852 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Acepromazine NuGOwiki Link

    HMDB15552 Metagene Link

    HMDB15552 METLIN ID

    Not Available PubChem Compound

    6077 PDB ID

    PMZ ChEBI ID

    44932

    Product: Piracetam

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
    Gene Name:
    DRD2
    Uniprot ID:
    P14416
    Molecular weight:
    50618.9
    References
    1. Oades RD, Rao ML, Bender S, Sartory G, Muller BW: Neuropsychological and conditioned blocking performance in patients with schizophrenia: assessment of the contribution of neuroleptic dose, serum levels and dopamine D2-receptor occupancy. Behav Pharmacol. 2000 Jun;11(3-4):317-30. [PubMed:11103886 ]
    2. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
    3. Wu S, Xing Q, Gao R, Li X, Gu N, Feng G, He L: Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients. Neurosci Lett. 2005 Mar 7;376(1):1-4. Epub 2004 Dec 2. [PubMed:15694263 ]
    4. Wu SN, Gao R, Xing QH, Li HF, Shen YF, Gu NF, Feng GY, He L: Association of DRD2 polymorphisms and chlorpromazine-induced extrapyramidal syndrome in Chinese schizophrenic patients. Acta Pharmacol Sin. 2006 Aug;27(8):966-70. [PubMed:16867246 ]
    5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    6. Seeman P: Dopamine D2 receptors as treatment targets in schizophrenia. Clin Schizophr Relat Psychoses. 2010 Apr;4(1):56-73. doi: 10.3371/CSRP.4.1.5. [PubMed:20643630 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
    Gene Name:
    HTR1A
    Uniprot ID:
    P08908
    Molecular weight:
    46106.3
    References
    1. Cosi C, Koek W: Agonist, antagonist, and inverse agonist properties of antipsychotics at human recombinant 5-HT(1A) receptors expressed in HeLa cells. Eur J Pharmacol. 2001 Dec 14;433(1):55-62. [PubMed:11755134 ]
    2. Newman-Tancredi A, Gavaudan S, Conte C, Chaput C, Touzard M, Verriele L, Audinot V, Millan MJ: Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study. Eur J Pharmacol. 1998 Aug 21;355(2-3):245-56. [PubMed:9760039 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
    Gene Name:
    HTR2A
    Uniprot ID:
    P28223
    Molecular weight:
    52602.6
    References
    1. Kusumi I, Takahashi Y, Suzuki K, Kameda K, Koyama T: Differential effects of subchronic treatments with atypical antipsychotic drugs on dopamine D2 and serotonin 5-HT2A receptors in the rat brain. J Neural Transm (Vienna). 2000;107(3):295-302. [PubMed:10821438 ]
    2. Yamada J, Sugimoto Y, Horisaka K: Serotonin2 (5-HT2) receptor agonist 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) inhibits chlorpromazine- and haloperidol-induced hypothermia in mice. Biol Pharm Bull. 1995 Nov;18(11):1580-3. [PubMed:8593484 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
    Gene Name:
    ADRA1A
    Uniprot ID:
    P35348
    Molecular weight:
    51486.0
    References
    1. Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
    Gene Name:
    ADRA1B
    Uniprot ID:
    P35368
    Molecular weight:
    56835.4
    References
    1. Cahir M, King DJ: Antipsychotics lack alpha 1A/B adrenoceptor subtype selectivity in the rat. Eur Neuropsychopharmacol. 2005 Mar;15(2):231-4. [PubMed:15695070 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
    Gene Name:
    DRD1
    Uniprot ID:
    P21728
    Molecular weight:
    49292.8
    References
    1. Kanba S, Suzuki E, Nomura S, Nakaki T, Yagi G, Asai M, Richelson E: Affinity of neuroleptics for D1 receptor of human brain striatum. J Psychiatry Neurosci. 1994 Jul;19(4):265-9. [PubMed:7918347 ]

    Transporters

    General function:
    Involved in ion transmembrane transporter activity
    Specific function:
    Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
    Gene Name:
    SLC22A1
    Uniprot ID:
    O15245
    Molecular weight:
    61187.4
    References
    1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]

    PMID: 12467901