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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
Structure of PROMAZINE PHOSPHATE

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)

HIDE SMILES / InChI

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

Description
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.

Originator

Sources: Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales (1947), 141, 1125-8

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
137 ng/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
132.2 μg × min/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1163 min
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
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
35.5%
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%
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%
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%
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

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Population Size: 16
Sources:
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
[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

Patents

Sample Use Guides

100-200 mg four times daily
Route of Administration: Oral
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 Sat Jun 26 01:09:10 UTC 2021
Edited
by admin
on Sat Jun 26 01:09:10 UTC 2021
Record UNII
M4011G9T8I
Record Status Validated (UNII)
Record Version
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Name Type Language
PROMAZINE PHOSPHATE
WHO-DD  
Common Name English
10-(3-(DIMETHYLAMINO)PROPYL)PHENOTHIAZINE PHOSPHATE
Systematic Name English
PROMAZINE PHOSPHATE [WHO-DD]
Common Name English
10H-PHENOTHIAZINE-10-PROPANAMINE, N,N-DIMETHYL-, PHOSPHATE
Systematic Name English
Code System Code Type Description
EVMPD
SUB04068MIG
Created by admin on Sat Jun 26 01:09:10 UTC 2021 , Edited by admin on Sat Jun 26 01:09:10 UTC 2021
PRIMARY
PUBCHEM
200325
Created by admin on Sat Jun 26 01:09:10 UTC 2021 , Edited by admin on Sat Jun 26 01:09:10 UTC 2021
PRIMARY
CAS
1508-27-6
Created by admin on Sat Jun 26 01:09:10 UTC 2021 , Edited by admin on Sat Jun 26 01:09:10 UTC 2021
PRIMARY
FDA UNII
M4011G9T8I
Created by admin on Sat Jun 26 01:09:10 UTC 2021 , Edited by admin on Sat Jun 26 01:09:10 UTC 2021
PRIMARY
Related Record Type Details
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