U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H19ClN2S
Molecular Weight 318.864
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORPROMAZINE

SMILES

CN(C)CCCN1C2=CC=CC=C2SC3=CC=C(Cl)C=C13

InChI

InChIKey=ZPEIMTDSQAKGNT-UHFFFAOYSA-N
InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C17H19ClN2S
Molecular Weight 318.864
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Chlorpromazine is a psychotropic agent indicated for the treatment of schizophrenia. It also exerts sedative and antiemetic activity. Chlorpromazine has actions at all levels of the central nervous system-primarily at subcortical levels-as well as on multiple organ systems. Chlorpromazine has strong antiadrenergic and weaker peripheral anticholinergic activity; ganglionic blocking action is relatively slight. It also possesses slight antihistaminic and antiserotonin activity. Chlorpromazine acts as an antagonist (blocking agent) on different postsysnaptic receptors -on dopaminergic-receptors (subtypes D1, D2, D3 and D4 - different antipsychotic properties on productive and unproductive symptoms), on serotonergic-receptors (5-HT1 and 5-HT2, with anxiolytic, antidepressive and antiaggressive properties as well as an attenuation of extrapypramidal side-effects, but also leading to weight gain, fall in blood pressure, sedation and ejaculation difficulties), on histaminergic-receptors (H1-receptors, sedation, antiemesis, vertigo, fall in blood pressure and weight gain), alpha1/alpha2-receptors (antisympathomimetic properties, lowering of blood pressure, reflex tachycardia, vertigo, sedation, hypersalivation and incontinence as well as sexual dysfunction, but may also attenuate pseudoparkinsonism - controversial) and finally on muscarinic (cholinergic) M1/M2-receptors (causing anticholinergic symptoms like dry mouth, blurred vision, obstipation, difficulty/inability to urinate, sinus tachycardia, ECG-changes and loss of memory, but the anticholinergic action may attenuate extrapyramidal side-effects). Additionally, Chlorpromazine is a weak presynaptic inhibitor of Dopamine reuptake, which may lead to (mild) antidepressive and antiparkinsonian effects. Chlorpromazine has being marketed under the trade names Thorazine and Largactil among others. Chlorpromazine is used for treating certain mental or mood disorders (eg, schizophrenia), the manic phase of manic-depressive disorder, anxiety and restlessness before surgery, the blood disease porphyria, severe behavioral and conduct disorders in children, nausea and vomiting, and severe hiccups.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
A comparative study of haloperidol and chlorpromazine in terms of clinical effects and therapeutic reversal with benztropine in schizophrenia. Theoretical implications for potency differences among neuroleptics.
1975 Aug 21
Letter: Side effects from lithium.
1975 Feb 22
Atypical tardive dyskinesia.
1975 May
Drug-induced dystonia.
1975 May
Effects of chlorpromazine on bilirubin metabolism and biliary secretion in the rat.
1975 Oct
Effects of chlorpromazine hydrochloride on bile salt synthesis, bile formation and biliary lipid secretion in the rhesus monkey: a model for chlorpromazine-induced cholestasis.
1979 Feb
Altered pilocarpine- or chlorpromazine-induced catalepsy after long-term treatment with cholinergic drugs.
1979 Nov
Chlorpromazine: a drug potentially useful for treating mycobacterial infections.
1992
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.
1992 Apr 10
Pharmacological characteristics of alpha 2-adrenergic receptors: comparison of pharmacologically defined subtypes with subtypes identified by molecular cloning.
1992 Jul
Effect of midodrine on chlorpromazine-induced orthostatic hypotension in rabbits: comparison with amezinium, etilefrine and droxidopa.
2000 Dec
Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors.
2000 Oct
Chlorpromazine induces apoptosis in activated human lymphoblasts: a mechanism supporting the induction of drug-induced lupus erythematosus?
2000 Sep
Chlorpromazine-induced cholestatic liver disease with ductopenia.
2001 Jul
Antipsychotic-induced extrapyramidal syndromes. Risperidone compared with low- and high-potency conventional antipsychotic drugs.
2001 Jul
Role of flavonoids in controlling the phototoxicity of Hypericum perforatum extracts.
2001 Jul
Torsades de pointes associated with chlorpromazine: case report and review of associated ventricular arrhythmias.
2001 Jul
Enhancement of antibiotic activity against poly-drug resistant Mycobacterium tuberculosis by phenothiazines.
2001 Mar
Bipolar disorder after mefloquine treatment.
2001 May
Activity of phenothiazines against antibiotic-resistant Mycobacterium tuberculosis: a review supporting further studies that may elucidate the potential use of thioridazine as anti-tuberculosis therapy.
2001 May
Iatrogenic cardiopulmonary arrest during pediatric sedation with meperidine, promethazine, and chlorpromazine.
2001 Oct
Oral contraceptives increase the plasma concentrations of chlorpromazine.
2001 Oct
Enhanced dendritic cell-driven proliferation and anti-HIV activity of CD8(+) T cells by a new phenothiazine derivative, aminoperazine.
2001 Sep 1
[Ultraviolet spectrophotometric determination of psychotropic drug mixtures].
2002
Specific and overlapping functions of the nuclear hormone receptors CAR and PXR in xenobiotic response.
2002
[Creutzfeldt-Jakob disease: diagnosis, incidence, prevention and treatment].
2002 Apr 20
Effects of chlorpromazine, pentoxifylline and dexamethasone on mRNA expression of lipopolysaccharide-induced inflammatory cytokines in bovine peripheral blood mononuclear cells.
2002 Aug
Carvedilol attenuates neuroleptic-induced orofacial dyskinesia: possible antioxidant mechanisms.
2002 May
Drugs used in the treatment of schizophrenia and bipolar disorder inhibit the replication of Toxoplasma gondii.
2003 Aug 1
Dual action of oestrogens on the mouse constitutive androstane receptor.
2003 Dec 1
Scopolamine-induced convulsions in fasted mice after food intake: determination of blood glucose levels, [3H]glutamate binding kinetics and antidopaminergic drug effects.
2003 Feb
[Reversal of multidrug resistance in leukemic cell line K562/AO2 by chlordelazine in vitro].
2003 Jul
QTc prolongation: chlorpromazine and high-dosage olanzapine.
2003 Jun
The antipsychotic drug chlorpromazine inhibits HERG potassium channels.
2003 Jun
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.
2003 Mar
Clinical concentrations of thioridazine kill intracellular multidrug-resistant Mycobacterium tuberculosis.
2003 Mar
New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis.
2003 May 10
Application of the CFU-GM assay to predict acute drug-induced neutropenia: an international blind trial to validate a prediction model for the maximum tolerated dose (MTD) of myelosuppressive xenobiotics.
2003 Oct
Sydenham's chorea may be a risk factor for drug induced parkinsonism.
2003 Sep
[Differences in prooxidant effect of neuroleptics haloperidol and aminazine].
2003 Sep-Oct
Two cases of deep vein thrombosis associated with antipsychotic drug use.
2004 Aug
Valproate-induced hyperammonemic encephalopathy.
2004 Aug
Smoking impact on CYP1A2 activity in a group of patients with schizophrenia.
2004 Jan
Block of HERG human K(+) channel and IKr of guinea pig cardiomyocytes by chlorpromazine.
2004 May
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system.
2005 Feb
New inhibitors of the Tat-TAR RNA interaction found with a "fuzzy" pharmacophore model.
2005 Jun
Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients.
2005 Mar 7
The effects of desmethylimipramine on cyclic AMP-stimulated gene transcription in a model cell system.
2005 Sep 1
Antipsychotic drugs inhibit the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells-an involvement of protein kinases.
2006 Apr
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Psychosis HOSPITALIZED PATIENTS: Acute Schizophrenia/Manic States: Oral: -Usual dose: 500 mg/day orally -Maximum dose: 2000 mg/day Parenteral: -Usual dose: 25 mg IM once, with a subsequent 25 to 50 mg injection in 1 hour if necessary -Maintenance dose: 400 mg IM every 4 to 6 hours until the patient is controlled Prompt Control of Severe Symptoms: Oral: -Usual dose: After an initial IM dose, 25 to 50 mg orally 3 times a day Parenteral: -Usual dose: 25 mg IV once, repeated in 1 hour if necessary Less Acutely Disturbed: Oral: -Initial dose: 25 mg orally 3 times a day -Usual dose: 400 mg/day Usual Adult Dose for Schizophrenia HOSPITALIZED PATIENTS: Acute Schizophrenia/Manic States: Oral: -Usual dose: 500 mg/day orally -Maximum dose: 2000 mg/day Parenteral: -Usual dose: 25 mg IM once, with a subsequent 25 to 50 mg injection in 1 hour if necessary -Maintenance dose: 400 mg IM every 4 to 6 hours until the patient is controlled Prompt Control of Severe Symptoms: Oral: -Usual dose: After an initial IM dose, 25 to 50 mg orally 3 times a day Parenteral: -Usual dose: 25 mg IV once, repeated in 1 hour if necessary Less Acutely Disturbed: Oral: -Initial dose: 25 mg orally 3 times a day -Usual dose: 400 mg/day
Route of Administration: oral, i.v., i.m.
In Vitro Use Guide
Chlorpromazine inhibited the serotonin2-mediated excitation of the interneurons of rat piriform cortex with an IC50 of 14 uM.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:48:08 UTC 2019
Edited
by admin
on Tue Oct 22 00:48:08 UTC 2019
Record UNII
U42B7VYA4P
Record Status Validated (UNII)
Record Version
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Name Type Language
CHLORPROMAZINE
HSDB   INN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN  
Official Name English
CHLORPROMAZINUM
HPUS  
Common Name English
ESMIND
Common Name English
CHLORPROMAZINE [MART.]
Common Name English
2-CHLORO-10-(3-(DIMETHYLAMINO)PROPYL)PHENOTHIAZINE
Systematic Name English
CHLORPROMAZINUM [HPUS]
Common Name English
NSC-226514
Code English
SANOPRON
Common Name English
CHLORPROMAZINE [VANDF]
Common Name English
CHLORPROMAZINE [INN]
Common Name English
J2.794D
Code English
SKF-2601A
Code English
CHLORPROMAZINE [HSDB]
Common Name English
NSC-167745
Code English
PROPAPHENIN
Common Name English
10H-PHENOTHIAZINE-10-PROPANAMINE, 2-CHLORO-N,N-DIMETHYL-
Systematic Name English
CPZ
Common Name English
3-(2-CHLORO-10H-PHENOTHIAZIN-10-YL)-N,N-DIMETHYLPROPAN-1-AMINE
Systematic Name English
LARGACTILOTHIAZINE
Common Name English
WINTERMIN
Common Name English
FENACTIL
Common Name English
CHLORPROMAZINE [USP]
Common Name English
CHLORPROMAZINE [ORANGE BOOK]
Common Name English
THORAZINE
Brand Name English
NOVOMAZINA
Common Name English
CHLORPROMAZINE [MI]
Common Name English
AMINAZINE
Common Name English
CHLORPROMAZINE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC N05AA01
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
NDF-RT N0000175746
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
NDF-RT N0000007544
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
WHO-VATC QN05AA01
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
NDF-RT N0000007544
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
NCI_THESAURUS C29710
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 24.1
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
NDF-RT N0000007544
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
NCI_THESAURUS C740
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
LIVERTOX 196
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL71
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
CAS
50-53-3
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
DRUG BANK
DB00477
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
IUPHAR
83
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
HSDB
50-53-3
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
NCI_THESAURUS
C367
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-045-8
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
EVMPD
SUB06208MIG
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
EPA CompTox
50-53-3
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
PUBCHEM
2726
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
INN
183
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
MERCK INDEX
M3461
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY Merck Index
LactMed
50-53-3
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
RXCUI
2403
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY RxNorm
EVMPD
SUB01255MIG
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
MESH
D002746
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
WIKIPEDIA
CHLORPROMAZINE
Created by admin on Tue Oct 22 00:48:09 UTC 2019 , Edited by admin on Tue Oct 22 00:48:09 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
METABOLIC ENZYME -> INHIBITOR
IC50
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
BINDING PROTEIN->LIGAND
chlorpromazine displayed an approximately 1:1 [drug:AGP] binding stoichiometry; DETERMINED BY ITC
BINDING
Kd
TARGET -> INHIBITOR
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
Metabolizing reaction by CYP2D6: N-demethylation Pharmacological action: Phenothiazine antipsychotic
SUBSTRATE
Unidentified
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC