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Identification
NameCarphenazine
Accession NumberDB01038  (APRD00848)
Typesmall molecule
Groupswithdrawn
Description

Carphenazine is an antipsychotic drug, used in hospitalized patients in the management of chronic schizophrenic psychoses.

Structure
Thumb
Synonyms
SynonymLanguageCode
CarfenazineNot AvailableINN
CarphenazinNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
ProcethazineNot Available
ProketazinNot Available
ProketazineWyeth
Brand mixturesNot Available
Categories
CAS number2622-30-2
WeightAverage: 411.56
Monoisotopic: 411.198047877
Chemical FormulaC23H29N3O2S
InChI KeyDYCNETKPCXPXNW-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(10-{2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl}-10H-phenothiazin-2-yl)propan-1-one
SMILES
CCC(=O)C1=CC2=C(SC3=C(C=CC=C3)N2CCN2CCN(CCO)CC2)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzothiazines
SubclassPhenothiazines
Direct parentPhenothiazines
Alternative parentsAcetophenones; Benzoyl Derivatives; Piperazines; Diazinanes; Tertiary Amines; Ketones; Enolates; Primary Alcohols; Polyamines; Thioethers
Substituentsacetophenone; benzoyl; 1,4-diazinane; benzene; piperazine; tertiary amine; ketone; enolate; thioether; polyamine; primary alcohol; alcohol; carbonyl group; amine; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
Pharmacology
IndicationUsed in the treatment of acute or chronic schizophrenic reactions in hospitalized patients.
PharmacodynamicsCarphenazine is a phenothiazine antipsychotic agent with a piperazine side-chain.
Mechanism of actionA 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 reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9941
Blood Brain Barrier + 0.9651
Caco-2 permeable - 0.5189
P-glycoprotein substrate Substrate 0.8797
P-glycoprotein inhibitor I Inhibitor 0.8874
P-glycoprotein inhibitor II Non-inhibitor 0.5543
Renal organic cation transporter Non-inhibitor 0.5663
CYP450 2C9 substrate Non-substrate 0.7229
CYP450 2D6 substrate Substrate 0.6853
CYP450 3A4 substrate Non-substrate 0.665
CYP450 1A2 substrate Inhibitor 0.7862
CYP450 2C9 substrate Non-inhibitor 0.9027
CYP450 2D6 substrate Inhibitor 0.8766
CYP450 2C19 substrate Non-inhibitor 0.7951
CYP450 3A4 substrate Non-inhibitor 0.6655
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5559
Ames test Non AMES toxic 0.8058
Carcinogenicity Non-carcinogens 0.8774
Biodegradation Not ready biodegradable 0.9848
Rat acute toxicity 2.6455 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8272
hERG inhibition (predictor II) Inhibitor 0.7613
Pharmacoeconomics
Manufacturers
  • Wyeth ayerst laboratories
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point175-177Tislow, R.F., Bruce, W.F. and Page, J.A.; US. Patent 3,023,146; February 27,1962; assigned to American Home Products Corporation. Sherlock, M.H. and Sperber, N.; US. Patent 2,985,654; May 23, 1961; assigned to Schering Corporation.
logP3.3Not Available
Predicted Properties
PropertyValueSource
water solubility9.05e-02 g/lALOGPS
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 area47.02ChemAxon
rotatable bond count7ChemAxon
refractivity121.46ChemAxon
polarizability47.25ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Tislow, R.F., Bruce, W.F. and Page, J.A.; US. Patent 3,023,146; February 27,1962; assigned to American Home Products Corporation.
Sherlock, M.H. and Sperber, N.; US. Patent 2,985,654; May 23, 1961; assigned to Schering
Corporation.

US3023146
General ReferenceNot Available
External Links
ResourceLink
ChEBI51235
ChEMBL
Therapeutic Targets DatabaseDAP000846
PharmGKBPA164750571
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. D(2) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(2) dopamine receptor P14416 Details

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
  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
  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
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. D(1A) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(1A) dopamine receptor P21728 Details

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
  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
  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

3. D(1B) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
D(1B) dopamine receptor P21918 Details

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
  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
  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

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Drug created on June 13, 2005 07:24 / Updated on April 02, 2014 14:39