Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H19ClN2S |
Molecular Weight | 318.864 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCCN1C2=C(SC3=C1C=C(Cl)C=C3)C=CC=C2
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16433053 | https://www.ncbi.nlm.nih.gov/pubmed/19300578
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
1.0 nM [IC50] | |||
Target ID: CHEMBL224 |
3.4 nM [IC50] | ||
Target ID: CHEMBL2056 |
56.0 nM [Ki] | ||
Target ID: CHEMBL231 |
12.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | THORAZINE Approved UseFor 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 Date1957 |
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Primary | THORAZINE Approved UseFor 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 Date1957 |
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Primary | THORAZINE Approved UseFor 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 Date1957 |
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Primary | THORAZINE Approved UseFor 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 Date1957 |
Cmax
Value | Dose | Co-administered | 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 | Co-administered | 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 |
T1/2
Value | Dose | Co-administered | 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 |
Funbound
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: |
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... Other AEs: Adverse event (grade 5) Sources: |
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... Other AEs: Adverse event (grade 5) Sources: |
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: |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
mild [IC50 52.2 uM] | ||||
weak [IC50 1000 uM] | ||||
yes [IC50 12 uM] | ||||
yes [IC50 14 uM] | ||||
yes [IC50 20 uM] | ||||
yes [IC50 5.8 uM] | ||||
Page: 6.0 |
yes [IC50 79 uM] | |||
yes [IC50 9.5 uM] | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
THE EFFECT OF L-3, 4-DIHYDROXYPHENYLALANINE AND DL-5-HYDROXYTRYPTOPHAN ON RIGIDITY AND TREMOR INDUCED BY RESERPINE, CHLORPROMAZINE AND PHENOXYBENZAMINE. | 1964 Apr |
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A case of phenobarbital exacerbation of a preexisting maladaptive behavior partially suppressed by chlorpromazine and misinterpreted as chlorpromazine efficacy. | 1992 |
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Levodopa-induced dyskinesias in Parkinson's disease: clinical and pharmacological classification. | 1992 |
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Chlorpromazine: a drug potentially useful for treating mycobacterial infections. | 1992 |
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Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor. | 1992 Apr 10 |
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An unusual cause of convulsions in a newborn infant. | 1992 Dec |
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Pharmacological characteristics of alpha 2-adrenergic receptors: comparison of pharmacologically defined subtypes with subtypes identified by molecular cloning. | 1992 Jul |
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Muscle pains and biochemical changes following suxamethonium administration after six pretreatment regimens. | 1992 Mar |
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[A case of neuroleptic malignant syndrome with acute renal failure]. | 1992 Nov |
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Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. | 1992 Sep |
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Drugs used in the treatment of schizophrenia and bipolar disorder inhibit the replication of Toxoplasma gondii. | 2003 Aug 1 |
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Dual action of oestrogens on the mouse constitutive androstane receptor. | 2003 Dec 1 |
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[Reversal of multidrug resistance in leukemic cell line K562/AO2 by chlordelazine in vitro]. | 2003 Jul |
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QTc prolongation: chlorpromazine and high-dosage olanzapine. | 2003 Jun |
|
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 |
|
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 |
|
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 |
|
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 |
|
UVA activated 8-MOP and chlorpromazine inhibit release of TNF-alpha by post-transcriptional regulation. | 2004 Apr |
|
Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. | 2004 Apr 15 |
|
Two cases of deep vein thrombosis associated with antipsychotic drug use. | 2004 Aug |
|
Valproate-induced hyperammonemic encephalopathy. | 2004 Aug |
|
Effects of lipopolysaccharide and chlorpromazine on glucocorticoid receptor-mediated gene transcription and immunoreactivity: a possible involvement of p38-MAP kinase. | 2004 Dec |
|
Smoking impact on CYP1A2 activity in a group of patients with schizophrenia. | 2004 Jan |
|
Spasmodic dysphonia, a rare form of tardive dystonia, induced by low-dose risperidone? | 2004 Mar |
|
Drug-induced liver injury. | 2004 Mar 1 |
|
Block of HERG human K(+) channel and IKr of guinea pig cardiomyocytes by chlorpromazine. | 2004 May |
|
Antipsychotics increase microtubule-associated protein 2 mRNA but not spinophilin mRNA in rat hippocampus and cortex. | 2004 May 1 |
|
Combined treatment of quetiapine with haloperidol in animal models of antipsychotic effect and extrapyramidal side effects: comparison with risperidone and chlorpromazine. | 2004 Oct |
|
Oral terbutaline in the management of pharmacologically induced prolonged erection. | 2004 Oct |
|
The phenothiazine drugs inhibit hERG potassium channels. | 2005 |
|
Intraoperative preparation of the radial artery for coronary artery bypass grafting. | 2005 |
|
Invited review: fluphenazine augments retinal oxidative stress. | 2005 Aug |
|
Effects of chlorpromazine with and without UV irradiation on gene expression of HepG2 cells. | 2005 Aug 4 |
|
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 |
|
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 |
|
[Thanatogenesis in poisoning with psychopharmaceuticals]. | 2005 Mar-Apr |
|
Stable expression of constitutively activated mutant h5HT6 and h5HT7 serotonin receptors: inverse agonist activity of antipsychotic drugs. | 2005 May |
|
Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates. | 2005 Nov |
|
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 |
|
Effect of chlorpromazine on bone sialoprotein (BSP) gene transcription. | 2006 Apr 15 |
|
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 |
|
Frequency of high-risk use of QT-prolonging medications. | 2006 Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/chlorpromazine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7513386
Chlorpromazine inhibited the serotonin2-mediated excitation of the interneurons of rat piriform cortex with an IC50 of 14 uM.
Substance Class |
Chemical
Created
by
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on
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Record UNII |
U42B7VYA4P
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Record Status |
Validated (UNII)
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WHO-ATC |
N05AA01
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NDF-RT |
N0000175746
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N0000007544
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QN05AA01
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C29710
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WHO-ESSENTIAL MEDICINES LIST |
24.1
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N0000007544
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C740
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NBK548793
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3649
Created by
admin on Fri Dec 15 15:15:15 GMT 2023 , Edited by admin on Fri Dec 15 15:15:15 GMT 2023
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BINDING PROTEIN->LIGAND |
chlorpromazine displayed an approximately 1:1 [drug:AGP] binding stoichiometry; DETERMINED BY ITC
BINDING
Kd
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE |
Metabolizing reaction by CYP2D6: N-demethylation
Pharmacological action: Phenothiazine antipsychotic
SUBSTRATE
Unidentified
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METABOLITE ACTIVE -> PARENT |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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