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Details

Stereochemistry ACHIRAL
Molecular Formula C17H20N2S
Molecular Weight 284.4208
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROMAZINE

SMILES

CN(C)CCCN1c2ccccc2Sc3ccccc31

InChI

InChIKey=ZGUGWUXLJSTTMA-UHFFFAOYSA-N
InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3

HIDE SMILES / InChI

Description
Curator's Comment:: 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

TargetsConditions
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
Health Status: unhealthy
Age Group: 79 years
Sex: M
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
Health Status: unhealthy
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
Health Status: unhealthy
Age Group: 79 years
Sex: M
Sources:
PubMed

PubMed

TitleDatePubMed
[Acute psychoses caused by digitalis poisoning].
1991 Nov-Dec
Conventional and atypical antipsychotics in the elderly : a review.
2003
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
Acute brain syndrome as a consequence of the Cronkhite-Canada syndrome.
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
Gastrointestinal bleeding and massive liver damage in neuroleptic malignant syndrome.
2005 Sep
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
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
Experimental design optimization of a sequential injection method for promazine assay in bulk and pharmaceutical formulations.
2007
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
Is the anti-psychotic, 10-(3-(dimethylamino)propyl)phenothiazine (promazine), a potential drug with which to treat SARS infections? Lack of efficacy of promazine on SARS-CoV replication in a mouse model.
2008 Aug
Determination of selected phenothiazines in human plasma by solid-phase extraction and liquid chromatography with coulometric detection.
2008 Aug 29
Capillary electrophoretic separation of tricyclic antidepressants using a polymer-coated capillary and beta-cyclodextrin as an electrolyte additive.
2008 Dec
Energetics of binding and protein unfolding upon amphiphilic drug complexation with a globular protein in different aqueous media.
2008 Jun 1
Comparative study of the efficiency of synthetic and natural mediators in laccase-assisted bleaching of eucalyptus kraft pulp.
2008 Nov
The cardiorespiratory effects of a fentanyl infusion following acepromazine and glycopyrrolate in dogs.
2008 Nov 1
Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients.
2008 Oct
[Determination of antidepressants in biological materials originating from victims of suicide by hanging].
2008 Oct-Dec
[Application of liquid chromatography coupled with mass spectrometry (LC/MS) to determine antidepressants in blood samples].
2008 Oct-Dec
P-glycoprotein senses its substrates and the lateral membrane packing density: consequences for the catalytic cycle.
2008 Sep 23
Valproate-induced delirium in a demented patient.
2009
[Drug-induced agranulocytosis--case reports and literature review].
2009
Rapid method for the determination of tranquilizers and a beta-blocker in porcine and bovine kidney by liquid chromatography with tandem mass spectrometry.
2009 Apr 1
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Acute intoxication by triazolam and promazine: a case report.
2009 Jan
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
Chemiluminescence determination of promazine in human serum and drug formulations using Ru(phen)3(2+)-Ce(IV) system and a chemometrical optimization approach.
2009 May-Jun
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
Name Type Language
PROMAZINE
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
PROMAZINE [WHO-DD]
Common Name English
COMBELEN
Brand Name English
CHLORPROMAZINE HYDROCHLORIDE IMPURITY C [EP]
Common Name English
PROMAZINE [INN]
Common Name English
PROMAZINE [HSDB]
Common Name English
NSC-31447
Code English
PROMAZINE [VANDF]
Common Name English
PROMAZINE [MI]
Common Name English
3-(10H-PHENOTHIAZIN-10-YL)-N,N-DIMETHYLPROPAN-1-AMINE
Systematic Name English
PROMAZINE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC N05AA03
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
WHO-VATC QN05AA03
Created by admin on Fri Jun 25 22:51:38 UTC 2021 , Edited by admin on Fri Jun 25 22:51:38 UTC 2021
NCI_THESAURUS C29710
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
CFR 21 CFR 520.1962
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
NCI_THESAURUS C740
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
Code System Code Type Description
INN
600
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
PUBCHEM
4926
Created by admin on Fri Jun 25 22:51:38 UTC 2021 , Edited by admin on Fri Jun 25 22:51:38 UTC 2021
PRIMARY
IUPHAR
7281
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
NCI_THESAURUS
C61908
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
EPA CompTox
58-40-2
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
MERCK INDEX
M9168
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
2284
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-382-0
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL564
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
DRUG BANK
DB00420
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
CAS
58-40-2
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
EVMPD
SUB10085MIG
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
MESH
D011395
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
RXCUI
8742
Created by admin on Fri Jun 25 22:51:38 UTC 2021 , Edited by admin on Fri Jun 25 22:51:38 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
PROMAZINE
Created by admin on Fri Jun 25 22:51:38 UTC 2021 , Edited by admin on Fri Jun 25 22:51:38 UTC 2021
PRIMARY
FDA UNII
O9M39HTM5W
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY
HSDB
3172
Created by admin on Fri Jun 25 22:51:37 UTC 2021 , Edited by admin on Fri Jun 25 22:51:37 UTC 2021
PRIMARY