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Acetophenazine

July 24, 2017
Common Name

Acetophenazine Description

Acetophenazine is only found in individuals that have used or taken this drug.It is an antipsychotic drug of moderate-potency. It is used in the treatment of disorganized and psychotic thinking. It is also used to help treat false perceptions (e.g. hallucinations or delusions).Acetophenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticliar activating system thus affecting basal metabolism, body temperature, wakefliness, vasomotor tone, and emesis. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source TindalChEMBL Acetophenazine, (Z)-2-maleate (1:2) saltMeSH Acetophenazine, ion (1+)MeSH Acetophenazine maleateMeSH

Chemical Formlia

C23H29N3O2S Average Molecliar Weight

411.56 Monoisotopic Molecliar Weight

411.198047877 IUPAC Name

1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)ethan-1-one Traditional Name

acetophenazine CAS Registry Number

2751-68-0 SMILES

CC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1

InChI Identifier

InChI=1S/C23H29N3O2S/c1-18(28)19-7-8-23-21(17-19)26(20-5-2-3-6-22(20)29-23)10-4-9-24-11-13-25(14-12-24)15-16-27/h2-3,5-8,17,27H,4,9-16H2,1H3

InChI Key

WNTYBHLDCKXEOT-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
  • N-alkylpiperazines
  • 1,4-thiazines
  • Trialkylamines
  • 1,2-aminoalcohols
  • Azacyclic compounds
  • Primary alcohols
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Acetophenone
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Aryl ketone
  • Aryl alkyl ketone
  • N-alkylpiperazine
  • Para-thiazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Ketone
  • Thioether
  • Azacycle
  • Alkanolamine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary alcohol
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • phenothiazines (CHEBI:2401 )
  • N-(2-hydroxyethyl)piperazine (CHEBI:2401 )
  • N-alkylpiperazine (CHEBI:2401 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antipsychotics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility6.01e-02 g/LNot Available LogP3.1Not Available

    Predicted Properties

    Property Value Source Water Solubility0.06 mg/mLALOGPS logP3.48ALOGPS logP2.65ChemAxon logS-3.8ALOGPS pKa (Strongest Acidic)15.46ChemAxon pKa (Strongest Basic)8.07ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area47.02 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity121.7 m3·mol-1ChemAxon Polarizability46.68 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key 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

  • 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 DB01063

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01063

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01063 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

    16708 KEGG Compound ID

    C06807 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Acetophenazine NuGOwiki Link

    HMDB15196 Metagene Link

    HMDB15196 METLIN ID

    Not Available PubChem Compound

    17676 PDB ID

    Not Available ChEBI ID

    2401

    Product: Goserelin

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851 ]
    2. Jones GL, Woodbury DM: Spin-label study of phenothiazine interactions with erythrocyte ghost membranes: a possible membrane-mediated antisickling action. J Pharmacol Exp Ther. 1978 Oct;207(1):203-11. [PubMed:702341 ]

    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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    3. Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
    4. Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851 ]
    5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

    PMID: 17240976

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