Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NamePromazine
Accession NumberDB00420  (APRD00358)
Typesmall molecule
Groups
Description

A phenothiazine with actions similar to chlorpromazine but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic. Promazine is not approved for use in the United States.

Structure
Thumb
Synonyms
SynonymLanguageCode
FrenilNot AvailableIS
N,N-dimethyl-3-(10H-phenothiazin-10-yl)-propan-1-amineNot AvailableIUPAC
PromazinGermanINN
Promazina SpanishINN
PromazinaNot AvailableINN
PromazineFrenchINN
PromazinumLatinINN
Salts
Name/CAS Structure Properties
Promazine Hydrochloride
53-60-1
Thumb
  • InChI Key: JIVSXRLRGOICGA-UHFFFAOYSA-N
  • Monoisotopic Mass: 320.111397079
  • Average Mass: 320.88
DBSALT000147
Brand names
NameCompany
CombelenNot Available
PrazinePliva
SparineNot Available
TalofenAbbott
Brand mixturesNot Available
Categories
CAS number58-40-2
WeightAverage: 284.419
Monoisotopic: 284.13471934
Chemical FormulaC17H20N2S
InChI KeyInChIKey=ZGUGWUXLJSTTMA-UHFFFAOYSA-N
InChI
InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3
IUPAC Name
dimethyl[3-(10H-phenothiazin-10-yl)propyl]amine
SMILES
CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12
Mass Specshow(9.05 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzothiazines
SubclassPhenothiazines
Direct parentPhenothiazines
Alternative parentsBenzene and Substituted Derivatives; Tertiary Amines; Polyamines; Thioethers
Substituentsbenzene; tertiary amine; thioether; polyamine; 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 as an adjunct for short term treatment of moderate and severe psychomotor agitation. Also used to treat agitation or restlessness in the elderly.
PharmacodynamicsPromazine belongs to a group of medications known as the phenothiazine antipsychotics. It acts by blocking a variety of receptors in the brain, particularly dopamine receptors. Dopamine is involved in transmitting signals between brain cells. When there is an excess amount of dopamine in the brain it causes over-stimulation of dopamine receptors. These receptors normally act to modify behaviour and over-stimulation may result in psychotic illness. Promazine hydrochloride blocks these receptors and stops them becoming over-stimulated, thereby helping to control psychotic illness. Promazine has weak extrapyramidal and autonomic side effects which lead to its use in the elderly, for restless or psychotic patients. Its anti-psychotic effect is also weaker and it is not useful in general psychiatry.
Mechanism of actionPromazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine.
AbsorptionAbsorption may be erratic and peak plasma concentrations show large interindividual differences.
Volume of distributionNot Available
Protein binding94%
Metabolism

Hepatic, primarily to N-desmethylpromazine and promazine sulfoxide.

SubstrateEnzymesProduct
Promazine
Promazine 5-sulfoxideDetails
Promazine
N-DesmethylpromazineDetails
Promazine
    3-HydroxypromazineDetails
    Route of eliminationNot Available
    Half lifeNot Available
    ClearanceNot Available
    ToxicitySide effects include: extrapyramidal symptoms, drowsiness, weight gain, dry mouth, constipation, endocrine effects (such as gynaecomastia and menstrual disturbance), sensitivity to sunlight and haemolytic anaemia.
    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 + 0.9718
    Blood Brain Barrier + 0.987
    Caco-2 permeable + 0.8813
    P-glycoprotein substrate Substrate 0.7933
    P-glycoprotein inhibitor I Inhibitor 0.6857
    P-glycoprotein inhibitor II Inhibitor 0.6352
    Renal organic cation transporter Inhibitor 0.7561
    CYP450 2C9 substrate Non-substrate 0.7526
    CYP450 2D6 substrate Substrate 0.9334
    CYP450 3A4 substrate Substrate 0.5578
    CYP450 1A2 substrate Inhibitor 0.8935
    CYP450 2C9 substrate Non-inhibitor 0.9483
    CYP450 2D6 substrate Inhibitor 0.9622
    CYP450 2C19 substrate Non-inhibitor 0.798
    CYP450 3A4 substrate Non-inhibitor 0.9166
    CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6784
    Ames test Non AMES toxic 0.9176
    Carcinogenicity Non-carcinogens 0.9545
    Biodegradation Not ready biodegradable 0.9921
    Rat acute toxicity 2.9416 LD50, mol/kg Not applicable
    hERG inhibition (predictor I) Weak inhibitor 0.9662
    hERG inhibition (predictor II) Inhibitor 0.7828
    Pharmacoeconomics
    Manufacturers
    • Wyeth ayerst laboratories
    • Watson laboratories inc
    • Baxter healthcare corp anesthesia critical care
    • Apothecon sub bristol myers squibb co
    • Apothecon inc div bristol myers squibb
    • Bristol myers squibb co
    Packagers
    Dosage forms
    FormRouteStrength
    LiquidIntramuscular
    Prices
    Unit descriptionCostUnit
    Chlorpromazine 25 mg/ml amp8.04USDml
    Chlorpromazine 200 mg tablet1.05USDtablet
    Chlorpromazine Hcl 25 mg/ml0.88USDml
    Chlorpromazine 100 mg tablet0.39USDtablet
    Novo-Chlorpromazine 100 mg Tablet0.35USDtablet
    Chlorpromazine 10 mg tablet0.32USDtablet
    Chlorpromazine 50 mg tablet0.3USDtablet
    Novo-Chlorpromazine 50 mg Tablet0.21USDtablet
    Novo-Chlorpromazine 25 mg Tablet0.18USDtablet
    Chlorpromazine 25 mg tablet0.17USDtablet
    DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
    PatentsNot Available
    Properties
    Stateliquid
    Experimental Properties
    PropertyValueSource
    melting point< 25 °CPhysProp
    boiling point203-210 °C at 3.00E-01 mm HgPhysProp
    water solubility14.2 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
    logP4.55HANSCH,C ET AL. (1995)
    logS-4.3ADME Research, USCD
    pKa9.36SANGSTER (1994)
    Predicted Properties
    PropertyValueSource
    water solubility2.07e-02 g/lALOGPS
    logP4.63ALOGPS
    logP3.93ChemAxon
    logS-4.1ALOGPS
    pKa (strongest basic)9.2ChemAxon
    physiological charge1ChemAxon
    hydrogen acceptor count2ChemAxon
    hydrogen donor count0ChemAxon
    polar surface area6.48ChemAxon
    rotatable bond count4ChemAxon
    refractivity88.95ChemAxon
    polarizability32.74ChemAxon
    number of rings3ChemAxon
    bioavailability1ChemAxon
    rule of fiveYesChemAxon
    Ghose filterYesChemAxon
    Veber's ruleYesChemAxon
    MDDR-like ruleNoChemAxon
    Spectra
    SpectraNot Available
    References
    Synthesis Reference

    DrugSyn.org

    US2519886
    General Reference
    1. Cubala WJ, Jakuszkowiak-Wojten K, Burkiewicz A, Wronska A: Promazine in the treatment of delusional parasitosis. Psychiatr Danub. 2011 Jun;23(2):198-9. Pubmed
    External Links
    ResourceLink
    KEGG DrugD08430
    KEGG CompoundC07379
    PubChem Compound4926
    PubChem Substance46504504
    ChemSpider4757
    ChEBI8459
    ChEMBLCHEMBL564
    Therapeutic Targets DatabaseDAP000430
    PharmGKBPA451126
    Drug Product Database497509
    WikipediaPromazine
    ATC CodesN05AA03N05AA02N05AA01N05AA04N05AA05
    AHFS Codes
    • 28:16.08.24
    PDB EntriesNot Available
    FDA labelNot Available
    MSDSshow(75.4 KB)
    Interactions
    Drug Interactions
    Drug
    BromocriptineThe phenothiazine decreases the effect of bromocriptine
    CisaprideIncreased risk of cardiotoxicity and arrhythmias
    DexfenfluramineDecreased anorexic effect, may increase psychotic symptoms
    DiethylpropionDecreased anorexic effect, may increase psychotic symptoms
    DonepezilPossible antagonism of action
    FenfluramineDecreased anorexic effect, may increase psychotic symptoms
    GalantaminePossible antagonism of action
    GatifloxacinIncreased risk of cardiotoxicity and arrhythmias
    GrepafloxacinIncreased risk of cardiotoxicity and arrhythmias
    GuanethidinePromazine may decrease the effect of guanethidine.
    LevofloxacinIncreased risk of cardiotoxicity and arrhythmias
    MazindolDecreased anorexic effect, may increase psychotic symptoms
    PhentermineDecreased anorexic effect, may increase psychotic symptoms
    PhenylpropanolamineDecreased anorexic effect, may increase psychotic symptoms
    TerfenadineIncreased risk of cardiotoxicity and arrhythmias
    Food InteractionsNot Available

    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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
    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

    2. 5-hydroxytryptamine receptor 2A

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    5-hydroxytryptamine receptor 2A P28223 Details

    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
    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
    3. Govitrapong P, Chagkutip J, Turakitwanakan W, Srikiatkhachorn A: Platelet 5-HT receptors in schizophrenic patients with and without neuroleptic treatment. Psychiatry Res. 2000 Sep 25;96(1):41-50. Pubmed
    4. Govitrapong P, Mukda S, Turakitwanakan W, Dumrongphol H, Chindaduangratn C, Sanvarinda Y: Platelet serotonin transporter in schizophrenic patients with and without neuroleptic treatment. Neurochem Int. 2002 Oct;41(4):209-16. Pubmed

    3. 5-hydroxytryptamine receptor 2C

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    5-hydroxytryptamine receptor 2C P28335 Details

    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
    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

    4. D(1A) dopamine receptor

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

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

    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
    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

    5. D(4) dopamine receptor

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    D(4) dopamine receptor P21917 Details

    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
    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

    6. Muscarinic acetylcholine receptor M4

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Muscarinic acetylcholine receptor M4 P08173 Details

    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
    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

    7. Muscarinic acetylcholine receptor M2

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Muscarinic acetylcholine receptor M2 P08172 Details

    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
    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

    8. Muscarinic acetylcholine receptor M3

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Muscarinic acetylcholine receptor M3 P20309 Details

    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
    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

    9. Muscarinic acetylcholine receptor M1

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Muscarinic acetylcholine receptor M1 P11229 Details

    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
    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

    10. Alpha-1B adrenergic receptor

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Alpha-1B adrenergic receptor P35368 Details

    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
    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

    11. Muscarinic acetylcholine receptor M5

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Muscarinic acetylcholine receptor M5 P08912 Details

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

    12. Alpha-1A adrenergic receptor

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Alpha-1A adrenergic receptor P35348 Details

    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
    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

    13. Histamine H1 receptor

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Histamine H1 receptor P35367 Details

    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
    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
    3. Hals PA, Hall H, Dahl SG: Muscarinic cholinergic and histamine H1 receptor binding of phenothiazine drug metabolites. Life Sci. 1988;43(5):405-12. Pubmed

    14. Alpha-1D adrenergic receptor

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: antagonist

    Components

    Name UniProt ID Details
    Alpha-1D adrenergic receptor P25100 Details

    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
    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

    1. Cytochrome P450 2C19

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate

    Components

    Name UniProt ID Details
    Cytochrome P450 2C19 P33261 Details

    References:

    1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
    2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

    2. Cytochrome P450 1A2

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate

    Components

    Name UniProt ID Details
    Cytochrome P450 1A2 P05177 Details

    References:

    1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
    2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

    3. Cytochrome P450 3A4

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate

    Components

    Name UniProt ID Details
    Cytochrome P450 3A4 P08684 Details

    References:

    1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
    2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

    4. Cytochrome P450 2C9

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: substrate

    Components

    Name UniProt ID Details
    Cytochrome P450 2C9 P11712 Details

    References:

    1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

    Comments
    Drug created on June 13, 2005 07:24 / Updated on March 11, 2014 11:09