Page last updated: 2024-12-05

trimeprazine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Trimeprazine: A phenothiazine derivative that is used as an antipruritic. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5574
CHEMBL ID829
CHEBI ID9725
SCHEMBL ID18993
MeSH IDM0021986

Synonyms (85)

Synonym
AC-19920
10h-phenothiazine-10-propanamine, n,n,.beta.-trimethyl-
n,n,2-trimethyl-3-(10h-phenothiazin-10-yl)propan-1-amine
n,n,beta-trimethyl-10h-phenothiazine-10-propanamine
alimemazine [inn:ban]
alimezine
dl-trimeprazine
phenothiazine, 10-(3-(dimethylamino)-2-methylpropyl)-
hsdb 3197
alimemazina [inn-spanish]
repetin
alimemazinum [inn-latin]
teralen
(+-)-alimemazine
(+-)-trimeprazine
einecs 201-577-3
bayer 1219
10-(3-(dimethylamino)-2-methylpropyl)phenothiazine
10-(2-methyl-3-dimethylaminopropyl)-phenothiazine
10h-phenothiazine-10-propanamine, n,n,beta-trimethyl-
nsc17476
QTL1_000086
trimeprazine (ban)
repeltin (tn)
D07125
alimemazine (inn)
AB00053560
84-96-8
methylpromazine
trimeprazine
C07172
alimemazine
DB01246
n,n,2-trimethyl-3-phenothiazin-10-yl-propan-1-amine
10-(3-dimethylamino-2-methylpropyl)phenothiazine
chebi:9725 ,
CHEMBL829 ,
rp-6549
bayer-1219
L000989
bdbm50062261
dimethyl-(2-methyl-3-phenothiazin-10-yl-propyl)-amine
n,n,2-trimethyl-3-phenothiazin-10-ylpropan-1-amine
alimemazina
76h78mjj52 ,
unii-76h78mjj52
alimemazinum
AKOS015963415
trimeperazine
gtpl7237
dimethyl[2-methyl-3-(10h-phenothiazin-10-yl)propyl]amine
alimemazine [inn]
(+/-)-alimemazine
alimemazine [hsdb]
trimeprazine [mi]
10h-phenothiazine-10-propanamine n,n,.beta.-trimethyl-
alimemazine [who-dd]
trimeprazine [vandf]
(+/-)-trimeprazine
SCHEMBL18993
vallergan (salt/mix)
nedeltran (salt/mix)
teralene
(.+/-.)-trimeprazine
temaril (salt/mix)
ZZHLYYDVIOPZBE-UHFFFAOYSA-N
10-[3-(dimethylamino)-2-methylpropyl]phenothiazine
n,n,2-trimethyl-3-(10h-phenothiazin-10-yl)-1-propanamine #
theralene (salt/mix)
phenothiazine, 10-[3-(dimethylamino)-2-methylpropyl]-
(.+/-.)-alimemazine
10-[2-methyl-3-(dimethylamino)propyl]phenothiazine
vanectyl (salt/mix)
AB00053560_08
DTXSID9023708
trimeprazine-d6
SBI-0051545.P002
84-96-8 (free base)
CS-0012341
HY-12752
Q2623251
BRD-A49225603-045-05-0
WDC60388
STARBLD0016703
EN300-18553889

Research Excerpts

Effects

ExcerptReferenceRelevance
"Trimeprazine (TPZ) has been marketed in France since 1959, as tablets and solution containing respectively 5 mg and 40 mg/ml. "( [Value of trimeprazine among hypnotics in a psychiatric facility].
Armand-Branger, S; Beauverie, P; Gaudoneix-Taieb, M; Mohammadi, R; Poisson, N,
)
1.98

Actions

ExcerptReferenceRelevance
"Trimeprazine could also inhibit strains of Shigella spp."( Studies on antimicrobial effect of the antihistaminic phenothiazine trimeprazine tartrate.
Chakrabarty, AN; Dastidar, SG; Jairaj, J; Mookerjee, M, 1997
)
1.25

Pharmacokinetics

ExcerptReferenceRelevance
"A simple and rapid method based on drop-to-drop solvent microextraction (DDSME) coupled with gas chromatography/mass spectrometry (GC/MS) has been successfully applied for the pharmacokinetic studies of trimeprazine in 8 microL of urine and blood samples of rats."( Drop-to-drop solvent microextraction coupled with gas chromatography/mass spectrometry for rapid determination of trimeprazine in urine and blood of rats: application to pharmacokinetic studies.
Agrawal, K; Wu, HF, 2007
)
0.74

Bioavailability

ExcerptReferenceRelevance
" The mean relative bioavailability for the tablets was approximately 70% with respect to the syrup."( Relative bioavailability of trimeprazine tablets investigated in man using HPLC with electrochemical detection.
Curry, SH; Gfeller, E; Hu, OY; Perrin, JH, 1986
)
0.57

Dosage Studied

ExcerptRelevanceReference
" The kinetic parameters showed substantial interindividual differences, and accordingly, major interindividual variations in drug response might be anticipated even on standardized dosage regimens."( Pharmacokinetics of trimeprazine in children.
Aune, H; Gulliksen, M; Mørland, J; Sponheim, S, 1990
)
0.6
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
phenothiazines
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
Alimemazine H1-Antihistamine Action87

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)73.72000.11007.190310.0000AID1449628
Trypanothione reductaseTrypanosoma cruziIC50 (µMol)249.00005.80005.80005.8000AID214488
Trypanothione reductaseTrypanosoma cruziKi127.00000.07605.15297.6000AID214654
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Histamine H2 receptorCavia porcellus (domestic guinea pig)K0.50.00020.00010.40364.8000AID88009
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID1148006Binding affinity to bovine serum albumin by circular dichroic probe technique1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Quantitative correlations between albumin binding constants and chromatographic Rm values of phenothiazine derivatives.
AID311935Partition coefficient, log P of the compound2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model.
AID311934Dissociation constant, pKa of the compound2008Journal of medicinal chemistry, Jan-24, Volume: 51, Issue:2
Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model.
AID75299Inhibitory activity against human erythrocyte glutathione reductase; '*' indicates No inhibition1998Journal of medicinal chemistry, Jan-15, Volume: 41, Issue:2
Phenothiazine inhibitors of trypanothione reductase as potential antitrypanosomal and antileishmanial drugs.
AID1148003Dissociation constant, pKa of the compound by UV-visible spectrophotometer analysis1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Quantitative correlations between albumin binding constants and chromatographic Rm values of phenothiazine derivatives.
AID214654Inhibitory activity against recombinant Trypanosoma cruzi (Trypanosoma cruzi) Trypanothione reductase (linear competitive type)1998Journal of medicinal chemistry, Jan-15, Volume: 41, Issue:2
Phenothiazine inhibitors of trypanothione reductase as potential antitrypanosomal and antileishmanial drugs.
AID781329pKa (acid-base dissociation constant) as determined by other workers2014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID214488Inhibitory activity against recombinant Trypanosoma cruzi (Trypanosoma cruzi) Trypanothione reductase1998Journal of medicinal chemistry, Jan-15, Volume: 41, Issue:2
Phenothiazine inhibitors of trypanothione reductase as potential antitrypanosomal and antileishmanial drugs.
AID781330pKa (acid-base dissociation constant) as determined by potentiometric titration2014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
AID1148004Oleyl alcohol-water partition coefficient, Rm of the compound measured at 0% methanol by reverse-phase thin layer chromatography1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Quantitative correlations between albumin binding constants and chromatographic Rm values of phenothiazine derivatives.
AID88009Displacement of [3H](-)-trans-H2-PAT from histamine H2 PAT binding site by competition binding assay.1999Journal of medicinal chemistry, Aug-12, Volume: 42, Issue:16
Synthesis, evaluation, and comparative molecular field analysis of 1-phenyl-3-amino-1,2,3,4-tetrahydronaphthalenes as ligands for histamine H(1) receptors.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (313)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990229 (73.16)18.7374
1990's44 (14.06)18.2507
2000's18 (5.75)29.6817
2010's18 (5.75)24.3611
2020's4 (1.28)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 45.82

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index45.82 (24.57)
Research Supply Index5.94 (2.92)
Research Growth Index4.35 (4.65)
Search Engine Demand Index75.16 (26.88)
Search Engine Supply Index2.06 (0.95)

This Compound (45.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials45 (13.51%)5.53%
Reviews7 (2.10%)6.00%
Case Studies25 (7.51%)4.05%
Observational1 (0.30%)0.25%
Other255 (76.58%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]