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Details

Stereochemistry ACHIRAL
Molecular Formula C17H19ClN2S.C14H10O4
Molecular Weight 561.091
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORPROMAZINE HIBENZATE

SMILES

OC(=O)C1=C(C=CC=C1)C(=O)C2=CC=C(O)C=C2.CN(C)CCCN3C4=C(SC5=C3C=C(Cl)C=C5)C=CC=C4

InChI

InChIKey=YCMNZFDJNUBQCQ-UHFFFAOYSA-N
InChI=1S/C17H19ClN2S.C14H10O4/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20;15-10-7-5-9(6-8-10)13(16)11-3-1-2-4-12(11)14(17)18/h3-4,6-9,12H,5,10-11H2,1-2H3;1-8,15H,(H,17,18)

HIDE SMILES / InChI

Molecular Formula C14H10O4
Molecular Weight 242.2268
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H19ClN2S
Molecular Weight 318.864
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Originator

Curator's Comment: Chlorpromazine was synthesized in December 1951 in the laboratories of Rhône-Poiulenc, and became available on prescription in France in November 1952.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
THORAZINE

Approved Use

For the treatment of schizophrenia; to control nausea and vomiting; for relief of restlessness and apprehension before surgery; for acute intermittent porphyria; as an adjunct in the treatment of tetanus; to control the manifestations of the manic type of manic-depressive illness; for relief of intractable hiccups; for the treatment of severe behavioral problems in children (1 to 12 years of age) marked by combativeness and/or explosive hyperexcitable behavior (out of proportion to immediate provocations), and in the short-term treatment of hyperactive children who show excessive motor activity with accompanying conduct disorders consisting of some or all of the following symptoms: impulsivity, difficulty sustaining attention, aggressivity, mood lability, and poor frustration tolerance.

Launch Date

1957
Primary
THORAZINE

Approved Use

For the treatment of schizophrenia; to control nausea and vomiting; for relief of restlessness and apprehension before surgery; for acute intermittent porphyria; as an adjunct in the treatment of tetanus; to control the manifestations of the manic type of manic-depressive illness; for relief of intractable hiccups; for the treatment of severe behavioral problems in children (1 to 12 years of age) marked by combativeness and/or explosive hyperexcitable behavior (out of proportion to immediate provocations), and in the short-term treatment of hyperactive children who show excessive motor activity with accompanying conduct disorders consisting of some or all of the following symptoms: impulsivity, difficulty sustaining attention, aggressivity, mood lability, and poor frustration tolerance.

Launch Date

1957
Primary
THORAZINE

Approved Use

For the treatment of schizophrenia; to control nausea and vomiting; for relief of restlessness and apprehension before surgery; for acute intermittent porphyria; as an adjunct in the treatment of tetanus; to control the manifestations of the manic type of manic-depressive illness; for relief of intractable hiccups; for the treatment of severe behavioral problems in children (1 to 12 years of age) marked by combativeness and/or explosive hyperexcitable behavior (out of proportion to immediate provocations), and in the short-term treatment of hyperactive children who show excessive motor activity with accompanying conduct disorders consisting of some or all of the following symptoms: impulsivity, difficulty sustaining attention, aggressivity, mood lability, and poor frustration tolerance.

Launch Date

1957
Primary
THORAZINE

Approved Use

For the treatment of schizophrenia; to control nausea and vomiting; for relief of restlessness and apprehension before surgery; for acute intermittent porphyria; as an adjunct in the treatment of tetanus; to control the manifestations of the manic type of manic-depressive illness; for relief of intractable hiccups; for the treatment of severe behavioral problems in children (1 to 12 years of age) marked by combativeness and/or explosive hyperexcitable behavior (out of proportion to immediate provocations), and in the short-term treatment of hyperactive children who show excessive motor activity with accompanying conduct disorders consisting of some or all of the following symptoms: impulsivity, difficulty sustaining attention, aggressivity, mood lability, and poor frustration tolerance.

Launch Date

1957
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
37.9 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.31 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
11.9 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
135 ng × h/mL
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
247 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
27.8 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
81.8 ng × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.1 h
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
11.05 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5.48 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
9.52 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROMAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
unknown, unknown
CHLORPROMAZINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
75 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 mg, 1 times / day
Sources:
unhealthy, 52 years (range: 36.5-65.6 years)
Health Status: unhealthy
Condition: agitation
Age Group: 52 years (range: 36.5-65.6 years)
Sex: M+F
Sources:
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, Elderly Patients
Health Status: unhealthy
Condition: Dementia-Related Psychosis
Age Group: Elderly Patients
Sources:
Other AEs: Adverse event...
25 mg 1 times / day multiple, intramuscular
Dose: 25 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, Elderly Patients
Health Status: unhealthy
Condition: Dementia-Related Psychosis
Age Group: Elderly Patients
Sources:
Other AEs: Adverse event...
AEs

AEs

AESignificanceDosePopulation
Adverse event grade 5
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, Elderly Patients
Health Status: unhealthy
Condition: Dementia-Related Psychosis
Age Group: Elderly Patients
Sources:
Adverse event grade 5
25 mg 1 times / day multiple, intramuscular
Dose: 25 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, Elderly Patients
Health Status: unhealthy
Condition: Dementia-Related Psychosis
Age Group: Elderly Patients
Sources:
Overview

Overview

OverviewOther

Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
THE EFFECT OF L-3, 4-DIHYDROXYPHENYLALANINE AND DL-5-HYDROXYTRYPTOPHAN ON RIGIDITY AND TREMOR INDUCED BY RESERPINE, CHLORPROMAZINE AND PHENOXYBENZAMINE.
1964 Apr
Deanol in the treatment of tardive dyskinesia.
1975 Aug
Atypical tardive dyskinesia.
1975 May
Drug-induced dystonia.
1975 May
The prolongation of QRS-duration resulting from delayed recovery of ventricular excitability. A new mechanism for intraventricular conduction disturbance. A preliminary note.
1976 Nov
Muscle pains and biochemical changes following suxamethonium administration after six pretreatment regimens.
1992 Mar
[A case of neuroleptic malignant syndrome with acute renal failure].
1992 Nov
Impaired extrapyramidal function caused by the targeted disruption of retinoid X receptor RXRgamma1 isoform.
1999 Apr
The use of a side effect as a qualitative indicator of plasma chlorpromazine levels.
1999 Jan
[Intractable vomiting, convulsions and megaloblastic anemia: anamnesis, key to diagnosis].
1999 Jul 3
Tardive dystonia induced by risperidone.
1999 Jun
Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs.
1999 Mar
Effect of some psychotropic drugs and a barbiturate on mycoplasmas.
2000 Apr
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.
2000 Jul 28
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
Potent synergism of the combination of fluconazole and cyclosporine in Candida albicans.
2000 Sep
Ca(2+)-calmodulin antagonist chlorpromazine and poly(ADP-ribose) polymerase modulators 4-aminobenzamide and nicotinamide influence hepatic expression of BCL-XL and P53 and protect against acetaminophen-induced programmed and unprogrammed cell death in mice.
2001 Aug 1
Antipsychotic-induced extrapyramidal syndromes. Risperidone compared with low- and high-potency conventional antipsychotic drugs.
2001 Jul
Combination of benzo[a]phenothiazines with acyclovir against herpes simplex virus.
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
Enhanced dendritic cell-driven proliferation and anti-HIV activity of CD8(+) T cells by a new phenothiazine derivative, aminoperazine.
2001 Sep 1
Specific and overlapping functions of the nuclear hormone receptors CAR and PXR in xenobiotic response.
2002
Effects of chlorpromazine, pentoxifylline and dexamethasone on mRNA expression of lipopolysaccharide-induced inflammatory cytokines in bovine peripheral blood mononuclear cells.
2002 Aug
Toxicity and carcinogenicity studies of chlorpromazine hydrochloride and p-cresidine in the p53 heterozygous mouse model.
2002 Nov-Dec
[The effect of microwaves on the bioelectric brain activity].
2002 Sep-Oct
Drugs used in the treatment of schizophrenia and bipolar disorder inhibit the replication of Toxoplasma gondii.
2003 Aug 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
Acute massive pulmonary thromboembolism associated with risperidone and conventional phenothiazines.
2003 Jan
[Reversal of multidrug resistance in leukemic cell line K562/AO2 by chlordelazine in vitro].
2003 Jul
The antipsychotic drug chlorpromazine inhibits HERG potassium channels.
2003 Jun
The steroid-responsive hiccup reflex arc: competitive binding to the corticosteroid-receptor?
2003 Jun-Aug
Variant Creutzfeldt-Jakob disease.
2003 Mar
Clinical concentrations of thioridazine kill intracellular multidrug-resistant Mycobacterium tuberculosis.
2003 Mar
Copper-stimulated endocytosis and degradation of the human copper transporter, hCtr1.
2003 Mar 14
Drug-induced liver injury.
2004 Mar 1
Antipsychotics increase microtubule-associated protein 2 mRNA but not spinophilin mRNA in rat hippocampus and cortex.
2004 May 1
Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland.
2005 Feb
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system.
2005 Feb
Response to chlorpromazine treatment may be associated with polymorphisms of the DRD2 gene in Chinese schizophrenic patients.
2005 Mar 7
Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.
2005 Nov
Antipsychotic drugs inhibit the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells-an involvement of protein kinases.
2006 Apr
Effect of chlorpromazine on bone sialoprotein (BSP) gene transcription.
2006 Apr 15
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Patents

Sample Use Guides

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: Other
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 Sat Dec 16 05:50:36 GMT 2023
Edited
by admin
on Sat Dec 16 05:50:36 GMT 2023
Record UNII
657G38Q829
Record Status Validated (UNII)
Record Version
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Name Type Language
CHLORPROMAZINE HIBENZATE
JAN   WHO-DD  
Common Name English
CHLORPROMAZINE HIBENZATE [JAN]
Common Name English
Chlorpromazine hibenzate [WHO-DD]
Common Name English
BENZOIC ACID, O-(P-HYDROXYBENZOYL)-, COMPD. WITH 2-CHLORO-10-(3-(DIMETHYLAMINO)PROPYL)PHENOTHIAZINE
Common Name English
BENZOIC ACID, O-(P-HYDROXYBENZOYL)-, SALT WITH 2-CHLORO-10-(3-DIMETHYLAMINOPROPYL)PHENOTHIAZINE
Common Name English
BENZOIC ACID, O-(P-HYDROXYBENZOYL)-, COMPD. WITH 2-CHLORO-10-(3-(DIMETHYLAMINO)PROPYL)PHENOTHIAZINE (1:1)
Common Name English
BENZOIC ACID, 2-(4-HYDROXYBENZOYL)-, COMPD. WITH 2-CHLORO-N,N-DIMETHYL-10H-PHENOTHIAZINE-10-PROPANAMINE (1:1)
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL71
Created by admin on Sat Dec 16 05:50:36 GMT 2023 , Edited by admin on Sat Dec 16 05:50:36 GMT 2023
PRIMARY
CAS
32043-97-3
Created by admin on Sat Dec 16 05:50:36 GMT 2023 , Edited by admin on Sat Dec 16 05:50:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID40185860
Created by admin on Sat Dec 16 05:50:36 GMT 2023 , Edited by admin on Sat Dec 16 05:50:36 GMT 2023
PRIMARY
PUBCHEM
6431825
Created by admin on Sat Dec 16 05:50:36 GMT 2023 , Edited by admin on Sat Dec 16 05:50:36 GMT 2023
PRIMARY
EVMPD
SUB22077
Created by admin on Sat Dec 16 05:50:36 GMT 2023 , Edited by admin on Sat Dec 16 05:50:36 GMT 2023
PRIMARY
SMS_ID
100000085394
Created by admin on Sat Dec 16 05:50:36 GMT 2023 , Edited by admin on Sat Dec 16 05:50:36 GMT 2023
PRIMARY
FDA UNII
657G38Q829
Created by admin on Sat Dec 16 05:50:36 GMT 2023 , Edited by admin on Sat Dec 16 05:50:36 GMT 2023
PRIMARY
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