Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H20N2S.H3O4P |
| Molecular Weight | 382.416 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCCN1c2ccccc2Sc3ccccc31.OP(=O)(O)O
InChI
InChIKey=WACBFIAINLBXOM-UHFFFAOYSA-N
InChI=1S/C17H20N2S.H3O4P/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19;1-5(2,3)4/h3-6,8-11H,7,12-13H2,1-2H3;(H3,1,2,3,4)
| Molecular Formula | H3O4P |
| Molecular Weight | 97.9952 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C17H20N2S |
| Molecular Weight | 284.4208 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment:: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00420 | https://www.ncbi.nlm.nih.gov/pubmed/22793499 | https://www.ncbi.nlm.nih.gov/pubmed/2863832 | https://www.ncbi.nlm.nih.gov/pubmed/12084453
Curator's Comment:: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00420 | https://www.ncbi.nlm.nih.gov/pubmed/22793499 | https://www.ncbi.nlm.nih.gov/pubmed/2863832 | https://www.ncbi.nlm.nih.gov/pubmed/12084453
Promazine (Sparine) is a phenothiazine neuroleptic used for short-term management of moderate to severe psychomotor agitation and treatment of agitation and restlessness in the elderly. Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tuberoinfundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine. Promazine is not approved for human use in the United States. It is available in the US for veterinary use under the names Promazine and Tranquazine.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL231 |
2.5 µM [IC50] | ||
Target ID: CHEMBL2096905 |
1.0 µM [IC50] | ||
Target ID: CHEMBL217 |
7.0 null [pKi] | ||
Target ID: CHEMBL224 |
7.9 null [pKi] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | THORAZINE Approved UseUnknown Launch Date-3.82319985E11 |
|||
| Primary | THORAZINE Approved UseUnknown Launch Date-3.82319985E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
137 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2265236/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
25 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9869384/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
71.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2265236/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
132.2 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7714731/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
45.7 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7714731/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1163 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7714731/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
558 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7714731/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
759 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2265236/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
613 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2265236/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
35.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7714731/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7714731/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
17% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2265236/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
|
16% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2265236/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROMAZINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
50 mg 1 times / day multiple, oral Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 79 years n = 1 Health Status: unhealthy Condition: Alzheimer’s disease Age Group: 79 years Sex: M Population Size: 1 Sources: |
Disc. AE: Drug eruption eczematous... AEs leading to discontinuation/dose reduction: Drug eruption eczematous (1 patient) Sources: |
50 mg single, intravenous Dose: 50 mg Route: intravenous Route: single Dose: 50 mg Sources: |
unhealthy n = 16 |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Drug eruption eczematous | 1 patient Disc. AE |
50 mg 1 times / day multiple, oral Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 79 years n = 1 Health Status: unhealthy Condition: Alzheimer’s disease Age Group: 79 years Sex: M Population Size: 1 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Acute psychoses caused by digitalis poisoning]. | 1991 Nov-Dec |
|
| Conventional and atypical antipsychotics in the elderly : a review. | 2003 |
|
| Peroxidase catalysed formation of cytotoxic prooxidant phenothiazine free radicals at physiological pH. | 2004 Dec 30 |
|
| Substitution and solvent effects on the photophysical properties of several series of 10-alkylated phenothiazine derivatives. | 2005 Apr 21 |
|
| Relation of postmortem blood alcohol and drug concentrations in fatal poisonings involving amitriptyline, propoxyphene and promazine. | 2005 Aug |
|
| Intrinsic efficacy of antipsychotics at human D2, D3, and D4 dopamine receptors: identification of the clozapine metabolite N-desmethylclozapine as a D2/D3 partial agonist. | 2005 Dec |
|
| Inhibition of rat liver CYP2D in vitro and after 1-day and long-term exposure to neuroleptics in vivo-possible involvement of different mechanisms. | 2005 Jan |
|
| Densitometric high performance thin-layer chromatography identification and quantitative analysis of psychotropic drugs. | 2005 Jan-Feb |
|
| Application notes on the use of softer X-rays for anomalous powder diffraction. | 2005 Jul |
|
| The in vitro activity of phenothiazines against Mycobacterium avium: potential of thioridazine for therapy of the co-infected AIDS patient. | 2005 Jul-Aug |
|
| Acute brain syndrome as a consequence of the Cronkhite-Canada syndrome. | 2005 Jun |
|
| Development and validation of a capillary electrophoresis method for the determination of phenothiazines in human urine in the low nanogram per milliliter concentration range using field-amplified sample injection. | 2005 Jun |
|
| Stability of the tranquilizer drug propionylpromazine hydrochloride in formulated products. | 2005 Jun |
|
| Models of treatment with antipsychotics of the schizophrenic patients. | 2005 Nov |
|
| Interactions between neuroleptics and CYP2C6 in rat liver--in vitro and ex vivo study. | 2005 Nov-Dec |
|
| Direct effects of neuroleptics on the activity of CYP2A in the liver of rats. | 2005 Nov-Dec |
|
| Antipsychotic drugs inhibit the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells-an involvement of protein kinases. | 2006 Apr |
|
| A kinetic study on the phenothiazine dependent oxidation of NADH by bovine ceruloplasmin. | 2006 Feb |
|
| Inhibitory effect of antipsychotic drugs on the Con A- and LPS-induced proliferative activity of mouse splenocytes: a possible mechanism of action. | 2006 Jun |
|
| Determination of phenothiazines in pharmaceutical formulations and human urine using capillary electrophoresis with chemiluminescence detection. | 2006 Jun |
|
| Interactions of recombinant prions with compounds of therapeutical significance. | 2006 Jun 2 |
|
| Characterization of human cytochrome p450 enzymes involved in the metabolism of the piperidine-type phenothiazine neuroleptic thioridazine. | 2006 Mar |
|
| Association between two distinct executive tasks in schizophrenia: a functional transcranial Doppler sonography study. | 2006 May 24 |
|
| Use of a fluorescent polarization based high throughput assay to identify new calmodulin ligands. | 2006 Nov |
|
| Trypanosoma cruzi dihydrolipoamide dehydrogenase as target for phenothiazine cationic radicals. Effect of antioxidants. | 2006 Sep |
|
| Drug adverse events and drop-out risk: a clinical case. | 2007 |
|
| The photo comet assay--a fast screening assay for the determination of photogenotoxicity in vitro. | 2007 Aug 15 |
|
| Modification of the thermal unfolding pathways of myoglobin upon drug interaction in different aqueous media. | 2007 Dec 13 |
|
| Affective psychosis, Hashimoto's thyroiditis, and brain perfusion abnormalities: case report. | 2007 Dec 20 |
|
| Thermodynamic studies of drug-alpha-cyclodextrin interactions in water at 298.15 K: promazine hydrochloride/chlorpromazine hydrochloride + alpha-cyclodextrin + H(2)O systems. | 2007 Dec 6 |
|
| Amiodarone inhibits tocopherol-mediated human lipoprotein peroxidation. | 2007 Jul 15 |
|
| Synthesis and antitubercular activity of quaternized promazine and promethazine derivatives. | 2007 Mar 1 |
|
| QTc and psychopharmacs: are there any differences between monotherapy and polytherapy. | 2007 May 3 |
|
| Inflammation-related genes up-regulated in schizophrenia brains. | 2007 Sep 6 |
|
| The activity of cytochrome P450 CYP2B in rat liver during neuroleptic treatment. | 2007 Sep-Oct |
|
| Neurosyphilis, malaria, and the discovery of antipsychotic agents. | 2008 |
|
| Palladium-catalyzed three-component approach to promazine with formation of one carbon-sulfur and two carbon-nitrogen bonds. | 2008 |
|
| The psychotropic drug olanzapine (Zyprexa) increases the area of acid glycerophospholipid monolayers. | 2008 Apr |
|
| Capillary electrophoretic separation of tricyclic antidepressants using a polymer-coated capillary and beta-cyclodextrin as an electrolyte additive. | 2008 Dec |
|
| Detection of photogenotoxicity in skin and eye in rat with the photo comet assay. | 2008 Feb |
|
| Energetics of binding and protein unfolding upon amphiphilic drug complexation with a globular protein in different aqueous media. | 2008 Jun 1 |
|
| [Application of liquid chromatography coupled with mass spectrometry (LC/MS) to determine antidepressants in blood samples]. | 2008 Oct-Dec |
|
| Valproate-induced delirium in a demented patient. | 2009 |
|
| [Drug-induced agranulocytosis--case reports and literature review]. | 2009 |
|
| Plasmids captured in C. metallidurans CH34: defining the PromA family of broad-host-range plasmids. | 2009 Aug |
|
| Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
|
| Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening. | 2009 Jul 14 |
|
| Simultaneous chemiluminescence determination of promazine and fluphenazine using support vector regression. | 2009 Jul 15 |
|
| Validation of derivative spectrophotometry method for determination of active ingredients from neuroleptics in pharmaceutical preparations. | 2009 Jul-Aug |
|
| Structure, function, regulation and polymorphism of human cytochrome P450 2A6. | 2009 Sep |
Patents
Sample Use Guides
African green monkey kidney cells (Vero 76) were used for activity evaluation. The cells were grown in minimal essential medium (MEM) supplemented with 10% heat-inactivated fetal bovine serum (FBS; Hyclone Laboratories; Logan UT). For antiviral assays, the serum was reduced to 2% and 50 µg/ml gentamicin added to the medium. Promazine was tested at varying concentrations (four log10 or eight 1/2 log10 dilutions). Virus and compound were added in equal volumes to near-confluent cell monolayers in 96- well tissue culture plates. The multiplicity of infection ranged from 0.001 to 0.004 in order to produce viral cytopathic effects (CPE) for each strain of virus in 100% of the cells in the virus control wells within 3–4 days. The plates were incubated at 37 °C in a 5% CO2 atmosphere until the cells in the virus control wells showed complete viral CPE as observed by light microscopy. Each concentration of drug was assayed for virus inhibition in triplicate and for cytotoxicity in duplicate. Six wells per plate were set aside as uninfected, untreated cell controls and six wells per plate received virus only and represented controls for virus replication. Calpain inhibitor IV was included as positive control drugs
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 01:09:10 UTC 2021
by
admin
on
Sat Jun 26 01:09:10 UTC 2021
|
| Record UNII |
M4011G9T8I
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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SUB04068MIG
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200325
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1508-27-6
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M4011G9T8I
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PARENT -> SALT/SOLVATE |
