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Carphenazine

July 24, 2017
Common Name

Carphenazine Description

Carphenazine is only found in individuals that have used or taken this drug. It is an antipsychotic drug, used in hospitalized patients in the management of chronic schizophrenic psychoses.A yellow, powdered, phenothiazine antipsychotic agent used in the treatment of acute or chronic schizophrenia. The term “phenothiazines” is used to describe the largest of the five main classes of neuroleptic antipsychotic drugs. These drugs have antipsychotic and, often, antiemetic properties, although they may also cause severe side effects such as akathisia, tardive dyskinesia and extrapyramidal symptoms. Carphenazine 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 1-(10-(3-(4-(2-Hydroxyethyl)-1-piperazinyl)propyl)phenothiazin-2-yl)-1-propanoneChEBI CarfenazinaChEBI CarfenazineChEBI CarfenazinumChEBI CarphenazinHMDB

Chemical Formlia

C23H29N3O2S Average Molecliar Weight

411.56 Monoisotopic Molecliar Weight

411.198047877 IUPAC Name

1-(10-{2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl}-10H-phenothiazin-2-yl)propan-1-one Traditional Name

carfenazina CAS Registry Number

2622-30-2 SMILES

CCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCN2CCN(CCO)CC2)C=C1

InChI Identifier

InChI=1S/C23H29N3O2S/c1-2-21(28)18-7-8-23-20(17-18)26(19-5-3-4-6-22(19)29-23)14-13-24-9-11-25(12-10-24)15-16-27/h3-8,17,27H,2,9-16H2,1H3

InChI Key

DYCNETKPCXPXNW-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
  • Aryl alkyl ketones
  • N-alkylpiperazines
  • Benzenoids
  • 1,4-thiazines
  • Trialkylamines
  • 1,2-aminoalcohols
  • Azacyclic compounds
  • Primary alcohols
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

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

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • phenothiazines (CHEBI:51235 )
  • propanone (CHEBI:51235 )
  • N-alkylpiperazine (CHEBI:51235 )

    • 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 Solubility9.05e-02 g/LNot Available LogP3.3Not Available

    Predicted Properties

    Property Value Source Water Solubility0.09 mg/mLALOGPS logP2.84ALOGPS logP3.29ChemAxon logS-3.7ALOGPS pKa (Strongest Acidic)15.56ChemAxon pKa (Strongest Basic)8ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area47.02 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity121.46 m3·mol-1ChemAxon Polarizability47.25 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 DB01038

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01038

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01038 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

    21865853 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15172 Metagene Link

    HMDB15172 METLIN ID

    Not Available PubChem Compound

    25137957 PDB ID

    Not Available ChEBI ID

    51235

    Product: Scopolamine (butylbromide)

    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. Vinar O, Formankova M, Taussigova D, Ruzicka S: Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial. Act Nerv Super (Praha). 1967 Nov;9(4):353-5. [PubMed:4889058 ]
    2. Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [PubMed:4887393 ]
    3. Platz AR, Klett CJ, Caffey EM Jr: Selective drug action related to chronic schizophrenic subtype. (A comparative study of carphenazine, chlorpromazine, and trifluoperazine). Dis Nerv Syst. 1967 Sep;28(9):601-5. [PubMed:4861216 ]
    4. 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. Vinar O, Formankova M, Taussigova D, Ruzicka S: Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial. Act Nerv Super (Praha). 1967 Nov;9(4):353-5. [PubMed:4889058 ]
    2. Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [PubMed:4887393 ]
    3. Platz AR, Klett CJ, Caffey EM Jr: Selective drug action related to chronic schizophrenic subtype. (A comparative study of carphenazine, chlorpromazine, and trifluoperazine). Dis Nerv Syst. 1967 Sep;28(9):601-5. [PubMed:4861216 ]
    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:
    DRD5
    Uniprot ID:
    P21918
    Molecular weight:
    52950.5
    References
    1. Vinar O, Formankova M, Taussigova D, Ruzicka S: Carphenazine in the treatment of schizophrenic psychoses. Controlled clinical trial. Act Nerv Super (Praha). 1967 Nov;9(4):353-5. [PubMed:4889058 ]
    2. Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [PubMed:4887393 ]
    3. Platz AR, Klett CJ, Caffey EM Jr: Selective drug action related to chronic schizophrenic subtype. (A comparative study of carphenazine, chlorpromazine, and trifluoperazine). Dis Nerv Syst. 1967 Sep;28(9):601-5. [PubMed:4861216 ]

    PMID: 27197150

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