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Aceprometazine

July 24, 2017
Common Name

Aceprometazine Description

Aceprometazine (INN) is a prescription drug with neuroleptic and anti-histamine properties. It is not widely prescribed. It may be used in combination with meprobamate for the treatment of sleep disorders. This combination is available in France under the trade name Mepronizine. [Wikipedia] Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 10-(2-(dimethylamino)Propyl)phenothiazin-2-yl methyl ketoneChEBI AceprometazinaChEBI AceprometazinumChEBI AcepromethazineChEBI Aceprometazine maleateMeSH

Chemical Formlia

C19H22N2OS Average Molecliar Weight

326.456 Monoisotopic Molecliar Weight

326.145284026 IUPAC Name

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

aceprometazine CAS Registry Number

13461-01-3 SMILES

CC(CN1C2=CC=CC=C2SC2=C1C=C(C=C2)C(C)=O)N(C)C

InChI Identifier

InChI=1S/C19H22N2OS/c1-13(20(3)4)12-21-16-7-5-6-8-18(16)23-19-10-9-15(14(2)22)11-17(19)21/h5-11,13H,12H2,1-4H3

InChI Key

XLOQNFNTQIRSOX-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:53770 )
  • tertiary amine (CHEBI:53770 )
  • methyl ketone (CHEBI:53770 )
  • aromatic ketone (CHEBI:53770 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antihistamines
  • Sedatives and Hypnotics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.22e-02 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.012 mg/mLALOGPS logP4.35ALOGPS logP3.85ChemAxon logS-4.4ALOGPS pKa (Strongest Acidic)16.06ChemAxon pKa (Strongest Basic)8.32ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area23.55 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity98.91 m3·mol-1ChemAxon Polarizability36.79 Å3ChemAxon Number of Rings3ChemAxon 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 DB01615

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01615

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01615 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

    24249 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Aceprometazine NuGOwiki Link

    HMDB15553 Metagene Link

    HMDB15553 METLIN ID

    Not Available PubChem Compound

    26035 PDB ID

    Not Available ChEBI ID

    53770

    Product: Methylcobalamin

    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:
    In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
    Gene Name:
    HRH1
    Uniprot ID:
    P35367
    Molecular weight:
    55783.6
    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. Mercier J, Dessaigne S, Menguy A, Manez J: Electro-encephalographic study on the action of the combination meprobamate-aceprometazine on various cerebral systems. Arzneimittelforschung. 1974 Feb;24(2):163-6. [PubMed:4406367 ]
    4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 2115588

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