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Details

Stereochemistry ACHIRAL
Molecular Formula C17H20N2S
Molecular Weight 284.419
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROMAZINE

SMILES

CN(C)CCCN1C2=C(SC3=C1C=CC=C3)C=CC=C2

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

Molecular Formula C17H20N2S
Molecular Weight 284.419
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
Application of reinecke salt and alizarin S for the determination of promazine.
2001 Aug
[Inactivation of Trypanosoma cruzi trypanothione reductase by phenothiazine cationic free radicals].
2001 Jan-Mar
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
Extractive-spectrophotometric determination of some 2- and 10-disubstituted phenothiazines with dipicrylamine.
2001 May-Jun
Solubilization of cationic drugs in lung surfactant.
2003 Nov
Analytical studies and application of reaction of promazine and thioridazine hydrochlorides with some oxidants.
2003 Nov-Dec
CSM thioridazine advice.
2004 Aug
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
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
Models of treatment with antipsychotics of the schizophrenic patients.
2005 Nov
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
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
Capillary electrophoretic separation of tricyclic antidepressants using a polymer-coated capillary and beta-cyclodextrin as an electrolyte additive.
2008 Dec
P-glycoprotein senses its substrates and the lateral membrane packing density: consequences for the catalytic cycle.
2008 Sep 23
[Drug-induced agranulocytosis--case reports and literature review].
2009
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Validation of derivative spectrophotometry method for determination of active ingredients from neuroleptics in pharmaceutical preparations.
2009 Jul-Aug
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 Fri Dec 15 15:17:01 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:01 GMT 2023
Record UNII
O9M39HTM5W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROMAZINE
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
COMBELEN
Brand Name English
Promazine [WHO-DD]
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
CHLORPROMAZINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-ATC N05AA03
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
WHO-VATC QN05AA03
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
CFR 21 CFR 520.1962
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
NCI_THESAURUS C740
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
Code System Code Type Description
INN
600
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
PUBCHEM
4926
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
IUPHAR
7281
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
NCI_THESAURUS
C61908
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID2023517
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
SMS_ID
100000092062
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
MERCK INDEX
m9168
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2284
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
CHEBI
8459
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-382-0
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
NSC
31447
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
ChEMBL
CHEMBL564
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
DRUG BANK
DB00420
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
CAS
58-40-2
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
EVMPD
SUB10085MIG
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
MESH
D011395
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
RXCUI
8742
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
PROMAZINE
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
FDA UNII
O9M39HTM5W
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
HSDB
3172
Created by admin on Fri Dec 15 15:17:02 GMT 2023 , Edited by admin on Fri Dec 15 15:17:02 GMT 2023
PRIMARY
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