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 Date-3.82319985E11 |
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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 Date-3.82319985E11 |
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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 Date-3.82319985E11 |
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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 Date-3.82319985E11 |
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 |
---|---|---|
Deanol in the treatment of tardive dyskinesia. | 1975 Aug |
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Drug-induced dystonia. | 1975 May |
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Effects of chlorpromazine on bilirubin metabolism and biliary secretion in the rat. | 1975 Oct |
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Altered pilocarpine- or chlorpromazine-induced catalepsy after long-term treatment with cholinergic drugs. | 1979 Nov |
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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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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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The use of a side effect as a qualitative indicator of plasma chlorpromazine levels. | 1999 Jan |
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Tardive dystonia induced by risperidone. | 1999 Jun |
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Potent synergism of the combination of fluconazole and cyclosporine in Candida albicans. | 2000 Sep |
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Role of flavonoids in controlling the phototoxicity of Hypericum perforatum extracts. | 2001 Jul |
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Combination of benzo[a]phenothiazines with acyclovir against herpes simplex virus. | 2001 Jul |
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Torsades de pointes associated with chlorpromazine: case report and review of associated ventricular arrhythmias. | 2001 Jul |
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Enhancement of antibiotic activity against poly-drug resistant Mycobacterium tuberculosis by phenothiazines. | 2001 Mar |
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Bipolar disorder after mefloquine treatment. | 2001 May |
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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 |
|
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 |
|
[Models of drug treatment in the attention deficit disorder with hyperactivity]. | 2002 Feb |
|
Carvedilol attenuates neuroleptic-induced orofacial dyskinesia: possible antioxidant mechanisms. | 2002 May |
|
Toxicity and carcinogenicity studies of chlorpromazine hydrochloride and p-cresidine in the p53 heterozygous mouse model. | 2002 Nov-Dec |
|
Dual action of oestrogens on the mouse constitutive androstane receptor. | 2003 Dec 1 |
|
Acute massive pulmonary thromboembolism associated with risperidone and conventional phenothiazines. | 2003 Jan |
|
QTc prolongation: chlorpromazine and high-dosage olanzapine. | 2003 Jun |
|
Examination of the functional activity of P-glycoprotein in the rat placental barrier using rhodamine 123. | 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 |
|
Copper-stimulated endocytosis and degradation of the human copper transporter, hCtr1. | 2003 Mar 14 |
|
New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis. | 2003 May 10 |
|
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 |
|
Drug-induced liver injury. | 2004 Mar 1 |
|
Block of HERG human K(+) channel and IKr of guinea pig cardiomyocytes by chlorpromazine. | 2004 May |
|
Oral terbutaline in the management of pharmacologically induced prolonged erection. | 2004 Oct |
|
Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates. | 2005 Nov |
|
Effect of chlorpromazine on bone sialoprotein (BSP) gene transcription. | 2006 Apr 15 |
|
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
admin
on
Edited
Fri Dec 16 16:36:58 UTC 2022
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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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N0000007544
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NCI_THESAURUS |
C29710
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WHO-ESSENTIAL MEDICINES LIST |
24.1
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N0000007544
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NCI_THESAURUS |
C740
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LIVERTOX |
NBK548793
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CHEMBL71
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50-53-3
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167745
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Chlorpromazine
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2403
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U42B7VYA4P
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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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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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
Metabolizing reaction by CYP2D6: N-demethylation
Pharmacological action: Phenothiazine antipsychotic
SUBSTRATE
Unidentified
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> 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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