Carphenazine
Identification
- Generic Name
- Carphenazine
- DrugBank Accession Number
- DB01038
- Background
Carphenazine is an antipsychotic drug, used in hospitalized patients in the management of chronic schizophrenic psychoses.
- Type
- Small Molecule
- Groups
- Withdrawn
- Structure
- Weight
- Average: 425.59
Monoisotopic: 425.213698424 - Chemical Formula
- C24H31N3O2S
- Synonyms
- Carfenazina
- Carfenazine
- Carfénazine
- Carfenazinum
- Carphenazine
Pharmacology
- Indication
Used in the treatment of acute or chronic schizophrenic reactions in hospitalized patients.
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- Pharmacodynamics
Carphenazine is a phenothiazine antipsychotic agent with a piperazine side-chain.
- Mechanism of action
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 reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.
Target Actions Organism ADopamine D2 receptor antagonistHumans ADopamine D1 receptor antagonistHumans ADopamine D5 receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareApomorphine The therapeutic efficacy of Apomorphine can be decreased when used in combination with Carphenazine. Aripiprazole The therapeutic efficacy of Aripiprazole can be decreased when used in combination with Carphenazine. Benzatropine The risk or severity of adverse effects can be increased when Carphenazine is combined with Benzatropine. Brexpiprazole The therapeutic efficacy of Brexpiprazole can be decreased when used in combination with Carphenazine. Bromocriptine The therapeutic efficacy of Bromocriptine can be decreased when used in combination with Carphenazine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Carphenazine maleate 0HX1Z0A2MC 2975-34-0 TVPJGGZLZLUPOB-SPIKMXEPSA-N - International/Other Brands
- Proketazin / Proketazine (Wyeth)
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiazines
- Sub Class
- Phenothiazines
- Direct Parent
- Phenothiazines
- Alternative Parents
- Alkyldiarylamines / Diarylthioethers / Aryl alkyl ketones / N-alkylpiperazines / Benzenoids / 1,4-thiazines / Trialkylamines / 1,2-aminoalcohols / Azacyclic compounds / Primary alcohols show 3 more
- Substituents
- 1,2-aminoalcohol / 1,4-diazinane / Alcohol / Alkanolamine / Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Aryl thioether show 20 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- CLY16Y8Z7E
- CAS number
- 2622-30-2
- InChI Key
- XZSMZRXAEFNJCU-UHFFFAOYSA-N
- InChI
- InChI=1S/C24H31N3O2S/c1-2-22(29)19-8-9-24-21(18-19)27(20-6-3-4-7-23(20)30-24)11-5-10-25-12-14-26(15-13-25)16-17-28/h3-4,6-9,18,28H,2,5,10-17H2,1H3
- IUPAC Name
- 1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one
- SMILES
- CCC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1
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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB15172
- PubChem Compound
- 18104
- PubChem Substance
- 46505936
- ChemSpider
- 17100
- ChEBI
- 51235
- ChEMBL
- CHEMBL1201328
- ZINC
- ZINC000022446644
- Therapeutic Targets Database
- DAP000846
- PharmGKB
- PA164750571
- Wikipedia
- Carfenazine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 175-177 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. logP 3.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0366 mg/mL ALOGPS logP 3.26 ALOGPS logP 3.35 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 15.56 Chemaxon pKa (Strongest Basic) 7.67 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 47.02 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 126.32 m3·mol-1 Chemaxon Polarizability 49.22 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.9027 CYP450 2D6 inhibitor Inhibitor 0.8766 CYP450 2C19 inhibitor Non-inhibitor 0.7951 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0010900000-d86dc6841f760f4bf205 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0000900000-220bb92f0e7145fd6454 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-0160900000-2621ce9b1557242397e1 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00fr-0009400000-57608800a18871fa0e3a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-006t-1509100000-24ba46fbfc8782e059c9 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0ug3-3159000000-0d2acf9134721f8c5889 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 197.84093 predictedDeepCCS 1.0 (2019) [M+H]+ 200.1989 predictedDeepCCS 1.0 (2019) [M+Na]+ 207.02301 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- 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. [Article]
- Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- CARPHENAZINE [Link]
- CHEBI:51235 - carphenazine [Link]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- D(1A) dopamine receptor
- Molecular Weight
- 49292.765 Da
References
- 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. [Article]
- Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- D(1B) dopamine receptor
- Molecular Weight
- 52950.5 Da
References
- 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. [Article]
- Bora G: Comparison of dosage ranges of carphenazine and trifluoperazine in elderly chronic schizophrenics. Dis Nerv Syst. 1968 Oct;29(10):695-7. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:54