Compound Detail

CHEMBL422

TRIFLUOPERAZINE

💊 Approved Drug

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💊 Approved Drug

CN1CCN(CCCN2c3ccccc3Sc3ccc(C(F)(F)F)cc32)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL422
Name	TRIFLUOPERAZINE
Phase	Approved
Structure Type	MOL
InChI Key	ZEWQUBUPAILYHI-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Amylozine Apo-trifluoperazine Flurazine NSC-17474 NSC-46061 RP-7623 Stelazine Stelazine fte Trifluoperazina Trifluoperazine

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

407.5

MW (Da)

4.95

ALogP

HBA

HBD

9.7

PSA (Å²)

0.71

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1959
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning

Extended Properties

Molecular Formula	C21H24F3N3S
MW	407.51
Aromatic Rings	2
Heavy Atoms	28
NP-Likeness	-1.51

Indications

Psychotic Disorders Anemia, Diamond-Blackfan

ATC Classification

N05AB06

trifluoperazine

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOLEPTICS

Activity Summary

IC50 60 meas. best 7.8

Kd 15 meas. best 9.27

Ki 13 meas. best 8.66

EC50 5 meas. best 5.87

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
D(2) dopamine receptor CHEMBL339	Kd	9.27	9.27	0.5	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Kd	8.98	8.98	1.0	1
D(2) dopamine receptor CHEMBL339	Ki	8.66	8.66	2.2	1
Emopamil-binding protein-like CHEMBL2311238	Ki	8.41	8.41	3.9	1
Serotonin 2 (5-HT2) receptor CHEMBL2093870	Ki	8.28	8.28	5.2	1
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase CHEMBL4931	Ki	8.1	8.1	8.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	7.82	7.82	15.0	1
D(2) dopamine receptor CHEMBL339	IC50	7.8	7.8	16.0	1
Unchecked CHEMBL612545	Ki	7.62	7.62	24.2	1
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	7.53	7.53	29.3	1
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	6.46	6.46	350.0	1
ADMET CHEMBL612558	Kd	6.41	6.41	392.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	6.39	6.39	411.0	1
C-8 sterol isomerase ERG2 CHEMBL3224	Ki	6.3	6.3	500.0	1
Unchecked CHEMBL612545	Kd	6.3	5.864	500.0	5
NS3 CHEMBL1293269	IC50	6.16	6.16	700.0	1
Calmodulin-1 CHEMBL6093	Kd	6.0	6.0	1000.0	1
N-formyl peptide receptor 2 CHEMBL4227	IC50	5.97	5.9667	1060.0	3
Unchecked CHEMBL612545	IC50	5.94	4.7867	1140.0	6
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	5.91	5.91	1230.0	1
Unchecked CHEMBL612545	EC50	5.87	5.6133	1340.0	3
Pleiotropic ABC efflux transporter of multiple drugs CHEMBL1697658	IC50	5.85	5.85	1400.0	1
Plasmodium falciparum CHEMBL364	IC50	5.83	5.525	1480.0	2
Nucleic Acid CHEMBL345	Kd	5.77	5.71	1700.0	3
Plasmodium falciparum CHEMBL364	EC50	5.72	5.72	1900.0	1
Rattus norvegicus CHEMBL376	IC50	5.57	5.094	2700.0	5
Neutrophil CHEMBL613710	IC50	5.57	5.1325	2700.0	4
Mycolicibacterium smegmatis CHEMBL613088	IC50	5.5	5.1067	3150.0	6
Calmodulin CHEMBL6092	Kd	5.47	5.385	3400.0	2
KG-1a CHEMBL4296453	IC50	5.34	5.34	4580.0	1
Sodium channel alpha subunits; brain (Types I, II, III) CHEMBL2096682	IC50	5.3	5.3	5000.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	Ki	5.29	5.29	5100.8	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.21	5.21	6226.0	1
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	5.2	5.1	6300.0	3
ATP-dependent translocase ABCB1 CHEMBL4302	Ki	5.19	5.19	6500.0	1
Beta-glucuronidase CHEMBL4814	IC50	5.11	5.11	7800.0	1
Ubiquitin carboxyl-terminal hydrolase 1/WD repeat-containing protein 48 CHEMBL3430885	IC50	5.1	5.1	8000.0	1
Lysozyme C CHEMBL2297	IC50	5.05	5.05	9000.0	1
U-87 MG CHEMBL614247	IC50	5.0	5.0	9900.0	1
NSC CHEMBL4296523	IC50	5.0	5.0	10100.0	1
Trypanosoma cruzi CHEMBL368	IC50	4.99	4.99	10130.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.96	4.8633	10990.0	6
MCF7 CHEMBL387	IC50	4.95	4.95	11330.0	1
U-87 MG CHEMBL614247	EC50	4.87	4.87	13500.0	1
Albumin CHEMBL4817	Kd	4.85	4.85	14000.0	1
SK-BR-3 CHEMBL613834	IC50	4.8	4.8	15890.0	1
SUM-159-PT CHEMBL4483269	IC50	4.77	4.77	17030.0	1
MDA-MB-231 CHEMBL400	IC50	4.67	4.67	21580.0	1
Trypanothione reductase CHEMBL5131	Ki	4.64	4.64	23000.0	1
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 CHEMBL4693	IC50	4.35	4.35	45000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Cmax	5.3	nM	Homo sapiens
Fu	0.0007	-	Rattus norvegicus
Fu	0.0018	-	Sus scrofa
Fu	0.0033	-	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
D(2) dopamine receptor	Kd	=	0.5322	nM	9.27	Compound was tested for its effect on dopamine saturation analysis	2869146
Serotonin 2 (5-HT2) receptor	Kd	=	1.043	nM	8.98	Compound was tested for its effect on 5-hydroxytryptamine 2 receptor saturation ...	2869146
D(2) dopamine receptor	Ki	=	2.2	nM	8.66	Binding affinity towards dopamine receptor D2 by displacing [3H]spiperone radiol...	1346653
Emopamil-binding protein-like	Ki	=	3.9	nM	8.41	Binding affinity to emopamil binding protein (unknown origin)	23199475
Serotonin 2 (5-HT2) receptor	Ki	=	5.2	nM	8.28	The compound was tested for its binding affinity towards 5-hydroxytryptamine 2 r...	1346653
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	Ki	=	8.0	nM	8.1	Affinity for human EMP expressed in ERG2 deficient strain of Saccharomyces cerev...	16033255
Sigma non-opioid intracellular receptor 1	Ki	=	15.0	nM	7.82	Affinity for sigma receptor type 1 of guinea pig using [3H]ifenprodil or (+)-[3H...	16033255
D(2) dopamine receptor	IC50	=	16.0	nM	7.8	Compound was tested in vitro for its affinity towards rat striatal Dopamine rece...	2869146
Unchecked	Ki	=	24.2	nM	7.62	Inhibition of human monobromobimane tagged-calmodulin L39C/V91C mutant by fluore...	21495717
Adrenergic receptor alpha-1	Ki	=	29.3	nM	7.53	The compound was tested for its binding affinity towards Alpha-1 adrenergic rece...	1346653
Adrenergic receptor alpha-1	IC50	=	350.0	nM	6.46	In vitro affinity for cortical alpha-1 adrenergic receptor labelled with [3H]WB-...	2869146
ADMET	Kd	=	392.0	nM	6.41	Binding affinity to Wistar rat brain lipid by TRANSIL assay	21071520
5-hydroxytryptamine receptor 1A	Ki	=	411.0	nM	6.39	Binding affinity towards 5-hydroxytryptamine 1A receptor by displacing [3H]WB-41...	1346653
C-8 sterol isomerase ERG2	Ki	=	500.0	nM	6.3	Affinity for ERG2 of Saccharomyces cerevisiae using [3H]ifenprodil or (+)-[3H]pe...	16033255
Unchecked	Kd	=	500.0	nM	6.3	Binding affinity to human monobromobimane tagged-calmodulin L39C/V91C mutant by ...	21495717
NS3	IC50	=	700.0	nM	6.16	Inhibitory concentration against hepatitis C virus helicase; range 0.6-0.7	15633995
Unchecked	Kd	=	800.0	nM	6.1	Binding affinity to human monobromobimane tagged-calmodulin L39C/V91C mutant by ...	21495717
Calmodulin-1	Kd	=	1000.0	nM	6.0	Binding affinity to calmodulin	18459732
Unchecked	Kd	=	1000.0	nM	6.0	Binding affinity to human monobromobimane tagged-calmodulin L39C/V91C mutant by ...	21495717
N-formyl peptide receptor 2	IC50	=	1060.0	nM	5.97	Fluorescence Polarization Assay: The competition binding assay was performed in ...	-

Literature References

PubMed	DOI	Target Context	# Activities
16472241	10.2174/1570163043334794	Hepatotoxicity	18
16510283	10.1016/j.bmcl.2006.02.005	Neutrophil	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
18024584	10.1073/pnas.0709695104	H4	13
19786608	10.1128/aac.00803-09	Mycolicibacterium smegmatis	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
21051535	10.1124/dmd.110.034629	ADMET	9
18694955	10.1128/aac.00661-08	NON-PROTEIN TARGET	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
21495717	10.1021/jm200167g	Unchecked	6
-	10.6019/CHEMBL4651402	SARS-CoV-2	4
29614416	10.1016/j.ejmech.2018.03.055	U-87 MG	4
12477351	10.1021/jm020941h	No relevant target	4
2869146	10.1021/jm00153a010	D(2) dopamine receptor	3
22480197	10.1021/jm2007694	Nucleic Acid	3
2869146	10.1021/jm00153a010	Rattus norvegicus	3
29859905	10.1016/j.bmcl.2018.05.048	Unchecked	3
11716514	10.1006/bbrc.2001.6000	ATP-dependent translocase ABCB1	3
29614416	10.1016/j.ejmech.2018.03.055	NSC	3
6167716	10.1021/jm00135a006	No relevant target	3

Data from ChEMBL 36 via Core Engine