CHLORPROMAZINE HIBENZATE

First approved in 1954

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 Search

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

Description
Sources: https://www.drugs.com/pro/chlorpromazine.html | https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=c63d6612-3fd2-44dd-a5c7-a093766b91f2&type=display | https://www.drugbank.ca/drugs/DB00477

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

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16867246 \| https://www.ncbi.nlm.nih.gov/pubmed/25557493 \| https://www.ncbi.nlm.nih.gov/pubmed/23919353 \| https://www.ncbi.nlm.nih.gov/pubmed/7918347	Antagonist 2778	1.0 nM [IC50]
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: https://www.drugbank.ca/drugs/DB00477 \| https://www.ncbi.nlm.nih.gov/pubmed/23919353	Antagonist 2778	3.4 nM [IC50]
Dopamine D1 receptor 101 Target ID: CHEMBL2056 Sources: https://www.drugbank.ca/drugs/DB00477 \| https://www.ncbi.nlm.nih.gov/pubmed/7918347	Antagonist 2778	56.0 nM [Ki]
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.drugbank.ca/drugs/DB00477 \| https://www.ncbi.nlm.nih.gov/pubmed/23919353	Antagonist 2778	12.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 298 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=c63d6612-3fd2-44dd-a5c7-a093766b91f2&type=display	Primary	Approved 8429	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
Manic-depressive disease 9 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=c63d6612-3fd2-44dd-a5c7-a093766b91f2&type=display	Primary	Approved 8429	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
Acute intermittent porphyria 7 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=c63d6612-3fd2-44dd-a5c7-a093766b91f2&type=display	Primary	Approved 8429	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
Nausea and vomiting 19 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=c63d6612-3fd2-44dd-a5c7-a093766b91f2&type=display	Primary	Approved 8429	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

C_max

Value	Dose	Analyte	Population
37.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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

Value	Dose	Analyte	Population
135 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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

T_1/2

Value	Dose	Analyte	Population
11.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8157044	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4399487	unknown, unknown		CHLORPROMAZINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/30558470	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: https://pubmed.ncbi.nlm.nih.gov/30558470	Sources: https://pubmed.ncbi.nlm.nih.gov/30558470
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: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=432cd4ca-c728-48ff-beec-2485f5e02512	unhealthy, Elderly Patients Health Status: unhealthy Condition: Dementia-Related Psychosis Age Group: Elderly Patients Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=432cd4ca-c728-48ff-beec-2485f5e02512	Other AEs: Adverse event... Other AEs: Adverse event (grade 5) Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=432cd4ca-c728-48ff-beec-2485f5e02512
25 mg 1 times / day multiple, intramuscular Dose: 25 mg, 1 times / day Route: intramuscular Route: multiple Dose: 25 mg, 1 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c0f1fcfd-8863-4032-bf80-185df60a4ba0	unhealthy, Elderly Patients Health Status: unhealthy Condition: Dementia-Related Psychosis Age Group: Elderly Patients Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c0f1fcfd-8863-4032-bf80-185df60a4ba0	Other AEs: Adverse event... Other AEs: Adverse event (grade 5) Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c0f1fcfd-8863-4032-bf80-185df60a4ba0

AEs

AE	Significance	Dose	Population
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: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=432cd4ca-c728-48ff-beec-2485f5e02512	unhealthy, Elderly Patients Health Status: unhealthy Condition: Dementia-Related Psychosis Age Group: Elderly Patients Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=432cd4ca-c728-48ff-beec-2485f5e02512
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: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c0f1fcfd-8863-4032-bf80-185df60a4ba0	unhealthy, Elderly Patients Health Status: unhealthy Condition: Dementia-Related Psychosis Age Group: Elderly Patients Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c0f1fcfd-8863-4032-bf80-185df60a4ba0

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737		inhibitor 1852 substrate 1217	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2E1 882 P-gp 1461 BCRP 699 UGT2B10 25 OCT2 647 OATP1A2 35	CYP1A2 1054 P-gp 1537	CYP2B 32 CYP3A 129

Drug as perpetrator

Target	Modality	Activity
BCRP 773	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2637613/	mild [IC50 52.2 uM]
CYP2E1 970	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15135088/	weak [IC50 1000 uM]
OATP1A2 35	inhibitor 3277 Sources: https://jpet.aspetjournals.org/content/352/3/552?cited-by=yes&legid=jpet%3B352/3/552	yes [IC50 12 uM]
OCT2 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19002438/	yes [IC50 14 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3586484/	yes [IC50 20 uM]
P-gp 1650	inhibitor 3277 Sources: https://link.springer.com/article/10.1007/s00213-006-0437-9?shared-article-renderer	yes [IC50 5.8 uM]
UGT2B10 27	inhibitor 3277 Sources: https://dmd.aspetjournals.org/content/dmd/44/3/378.full.pdf#page=6 Page: 6.0	yes [IC50 79 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3586484/	yes [IC50 9.5 uM]
CYP2B 40	inducer 1573 Sources: https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1600-0773.1999.tb02018.x	yes
CYP3A 298	inducer 1573 Sources: https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1600-0773.1999.tb02018.x	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://www.longdom.org/open-access/cyp450-and-its-implications-in-the-clinical-use-of-antipsychotic-drugs-2161-1459-1000176.pdf Page: 4.0	yes
CYP2D6 1217	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S1110863017300228	yes
CYP3A4 1737	substrate 3367 Sources: https://www.longdom.org/open-access/cyp450-and-its-implications-in-the-clinical-use-of-antipsychotic-drugs-2161-1459-1000176.pdf Page: 4.0	yes
P-gp 1537	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3913737/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1573882/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3647	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3647
ChemicalBook	CB5547531	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5547531
MolPort	MolPort-001-727-953	https://www.molport.com/shop/molecule-link/MolPort-001-727-953
ZINC	ZINC000000044027	http://zinc15.docking.org/substances/ZINC000000044027
eMolecules	730270	https://www.emolecules.com/cgi-bin/more?vid=730270

PubMed

Title	Date	PubMed
Deanol in the treatment of tardive dyskinesia.	1975 Aug	1147074
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	1103205
Letter: Side effects from lithium.	1975 Feb 22	1111885
Atypical tardive dyskinesia.	1975 May	1119614
[Chronic intrahepatic cholestasis following chlorpromazine; treated using phenobarbital].	1976	1088626
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	110598
A case of phenobarbital exacerbation of a preexisting maladaptive behavior partially suppressed by chlorpromazine and misinterpreted as chlorpromazine efficacy.	1992	1509179
Chlorpromazine: a drug potentially useful for treating mycobacterial infections.	1992	1288966
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.	1992 Apr 10	1354163
An unusual cause of convulsions in a newborn infant.	1992 Dec	1473547
Pharmacological characteristics of alpha 2-adrenergic receptors: comparison of pharmacologically defined subtypes with subtypes identified by molecular cloning.	1992 Jul	1353247
Muscle pains and biochemical changes following suxamethonium administration after six pretreatment regimens.	1992 Mar	1566986
[Intractable vomiting, convulsions and megaloblastic anemia: anamnesis, key to diagnosis].	1999 Jul 3	10431323
Effect of some psychotropic drugs and a barbiturate on mycoplasmas.	2000 Apr	10773494
Synthesis and biological activity of N-acylphenothiazines.	2000 Apr	10773488
Double-blind crossover study of chlorpromazine and lorazepam in the treatment of behavioral problems during treatment of children with acute lymphoblastic leukaemia receiving glucocorticoids.	2000 Apr	10742070
Effect of midodrine on chlorpromazine-induced orthostatic hypotension in rabbits: comparison with amezinium, etilefrine and droxidopa.	2000 Dec	11145175
Block of rat brain recombinant SK channels by tricyclic antidepressants and related compounds.	2000 Jul 28	10915830
Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors.	2000 Oct	10991983
Chlorpromazine induces apoptosis in activated human lymphoblasts: a mechanism supporting the induction of drug-induced lupus erythematosus?	2000 Sep	11014349
Potent synergism of the combination of fluconazole and cyclosporine in Candida albicans.	2000 Sep	10952582
Evaluation of a vincristine resistant Caco-2 cell line for use in a calcein AM extrusion screening assay for P-glycoprotein interaction.	2001 Jan	11113639
Chlorpromazine-induced cholestatic liver disease with ductopenia.	2001 Jul	11669021
Torsades de pointes associated with chlorpromazine: case report and review of associated ventricular arrhythmias.	2001 Jul	11444585
Enhancement of antibiotic activity against poly-drug resistant Mycobacterium tuberculosis by phenothiazines.	2001 Mar	11282269
Bipolar disorder after mefloquine treatment.	2001 May	11394195
Enhanced dendritic cell-driven proliferation and anti-HIV activity of CD8(+) T cells by a new phenothiazine derivative, aminoperazine.	2001 Sep 1	11509641
Specific and overlapping functions of the nuclear hormone receptors CAR and PXR in xenobiotic response.	2002	12049174
Effects of chlorpromazine, pentoxifylline and dexamethasone on mRNA expression of lipopolysaccharide-induced inflammatory cytokines in bovine peripheral blood mononuclear cells.	2002 Aug	12237520
Carvedilol attenuates neuroleptic-induced orofacial dyskinesia: possible antioxidant mechanisms.	2002 May	12010767
Scopolamine-induced convulsions in fasted mice after food intake: determination of blood glucose levels, [3H]glutamate binding kinetics and antidopaminergic drug effects.	2003 Feb	12623218
Variant Creutzfeldt-Jakob disease.	2003 Mar	12733426
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.	2003 Mar	12629531
Copper-stimulated endocytosis and degradation of the human copper transporter, hCtr1.	2003 Mar 14	12501239
New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis.	2003 May 10	12747876
Mechanism of C2-toxin inhibition by fluphenazine and related compounds: investigation of their binding kinetics to the C2II-channel using the current noise analysis.	2003 Oct 24	14556742
[Differences in prooxidant effect of neuroleptics haloperidol and aminazine].	2003 Sep-Oct	14650217
Valproate-induced hyperammonemic encephalopathy.	2004 Aug	15266186
Effects of lipopolysaccharide and chlorpromazine on glucocorticoid receptor-mediated gene transcription and immunoreactivity: a possible involvement of p38-MAP kinase.	2004 Dec	15589393
Smoking impact on CYP1A2 activity in a group of patients with schizophrenia.	2004 Jan	14659985
Drug-induced liver injury.	2004 Mar 1	14986274
Oral terbutaline in the management of pharmacologically induced prolonged erection.	2004 Oct	14999218
Intraoperative preparation of the radial artery for coronary artery bypass grafting.	2005	16037812
Effects of chlorpromazine with and without UV irradiation on gene expression of HepG2 cells.	2005 Aug 4	15924885
Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland.	2005 Feb	15674093
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system.	2005 Feb	15342952
[Thanatogenesis in poisoning with psychopharmaceuticals].	2005 Mar-Apr	15881137
Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.	2005 Nov	16251329
The effects of desmethylimipramine on cyclic AMP-stimulated gene transcription in a model cell system.	2005 Sep 1	16036225
Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways.	2006 Feb 1	16178010

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: 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

Download

Name

Type

Language

CHLORPROMAZINE HIBENZATE

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