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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
Carfenazine
Carphenazin
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
ProcethazineNot Available
ProketazinNot Available
ProketazineWyeth
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Carphenazine maleate
ThumbNot applicableDBSALT001419
Categories
UNIICLY16Y8Z7E
CAS number2622-30-2
WeightAverage: 411.56
Monoisotopic: 411.198047877
Chemical FormulaC23H29N3O2S
InChI KeyInChIKey=DYCNETKPCXPXNW-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • N-alkylpiperazine
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Para-thiazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • 1,2-aminoalcohol
  • Azacycle
  • Thioether
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9941
Blood Brain Barrier+0.9651
Caco-2 permeable-0.5189
P-glycoprotein substrateSubstrate0.8797
P-glycoprotein inhibitor IInhibitor0.8874
P-glycoprotein inhibitor IINon-inhibitor0.5543
Renal organic cation transporterNon-inhibitor0.5663
CYP450 2C9 substrateNon-substrate0.7229
CYP450 2D6 substrateSubstrate0.6853
CYP450 3A4 substrateNon-substrate0.665
CYP450 1A2 substrateInhibitor0.7862
CYP450 2C9 inhibitorNon-inhibitor0.9027
CYP450 2D6 inhibitorInhibitor0.8766
CYP450 2C19 inhibitorNon-inhibitor0.7951
CYP450 3A4 inhibitorNon-inhibitor0.6655
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5559
Ames testNon AMES toxic0.8058
CarcinogenicityNon-carcinogens0.8774
BiodegradationNot ready biodegradable0.9848
Rat acute toxicity2.6455 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8272
hERG inhibition (predictor II)Inhibitor0.7613
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
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 Solubility0.0905 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Carphenazine.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Carphenazine.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Carphenazine.
AmphetamineCarphenazine may decrease the stimulatory activities of Amphetamine.
BenzphetamineCarphenazine may decrease the stimulatory activities of Benzphetamine.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Carphenazine.
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Carphenazine.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Carphenazine.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Carphenazine.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Carphenazine.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Carphenazine.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Carphenazine.
DextroamphetamineCarphenazine may decrease the stimulatory activities of Dextroamphetamine.
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Carphenazine.
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Carphenazine.
DonepezilDonepezil may increase the central neurotoxic activities of Carphenazine.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Carphenazine.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Carphenazine.
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Carphenazine.
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Carphenazine.
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Carphenazine.
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Carphenazine.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Carphenazine.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Carphenazine.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Carphenazine.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Carphenazine.
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Carphenazine.
GalantamineGalantamine may increase the central neurotoxic activities of Carphenazine.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Carphenazine.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Carphenazine.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Carphenazine.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Carphenazine.
LisdexamfetamineCarphenazine may decrease the stimulatory activities of Lisdexamfetamine.
LithiumLithium may increase the neurotoxic activities of Carphenazine.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Carphenazine.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Carphenazine.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Carphenazine.
MethamphetamineCarphenazine may decrease the stimulatory activities of Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Carphenazine is combined with Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Carphenazine.
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Carphenazine.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Carphenazine.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Carphenazine.
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Carphenazine.
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Carphenazine.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Carphenazine.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Carphenazine.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Carphenazine.
PhendimetrazineCarphenazine may decrease the stimulatory activities of Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Carphenazine.
PhentermineCarphenazine may decrease the stimulatory activities of Phentermine.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Carphenazine.
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Carphenazine.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Carphenazine.
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Carphenazine.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Carphenazine.
RivastigmineRivastigmine may increase the central neurotoxic activities of Carphenazine.
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Carphenazine.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Carphenazine.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Carphenazine.
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Carphenazine.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Carphenazine.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Carphenazine.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Carphenazine.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Carphenazine.
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Carphenazine.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Carphenazine.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Carphenazine.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Carphenazine.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Carphenazine.
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Carphenazine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular Weight:
49292.765 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
G-protein coupled amine receptor activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name:
DRD5
Uniprot ID:
P21918
Molecular Weight:
52950.5 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on November 30, 2015 12:10