Trifluoperazine

Details

• Internal ID: 87d469c9-6edd-44b3-b273-2104af3f0312
• Taxonomy: Organoheterocyclic compounds > Benzothiazines > Phenothiazines
• IUPAC Name: 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine
• SMILES (Canonical): CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F
• SMILES (Isomeric): CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F
• InChI: InChI=1S/C21H24F3N3S/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24/h2-3,5-8,15H,4,9-14H2,1H3
• InChI Key: ZEWQUBUPAILYHI-UHFFFAOYSA-N
• Popularity: 6,845 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄F₃N₃S
• Molecular Weight: 407.50 g/mol
• Exact Mass: 407.16430344 g/mol
• Topological Polar Surface Area (TPSA): 35.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.95
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 117-89-5
• Trifluperazine
• Trifluoroperazine
• Flurazine
• Trifluoperazin
• Triflurin
• Triperazine
• Trifluoperazina
• Trifluoromethylperazine
• Trifluoperazinum
• Trifluroperizine
• Apo-Trifluoperazine
• Eskazine
• Trifluoperazina [Italian]
• 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine
• RP 7623
• Fluoperazine
• Trifluoperazine [INN:BAN]
• TFP
• Trifluoperazinum [INN-Latin]
• Trifluoperazina [INN-Spanish]
• Flupazine
• Trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazine
• NSC 17474
• Triphthasine
• 10-(3-(4-methylpiperazin-1-yl)propyl)-2-(trifluoromethyl)-10H-phenothiazine
• Calmazine
• Modalina
• CCRIS 6994
• C21H24F3N3S
• HSDB 3195
• Trifluoperazine (INN)
• 10-(3-(4-Methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)phenothiazine
• 10-[3-(4-Methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazine
• 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine
• 10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-
• EINECS 204-219-4
• Apo-trifluoperazine (TN)
• NSC 46061
• NSC-17474
• 10-(gamma-(N'-Methylpiperazino)propyl)-2-trifluoromethylphenothiazine
• Tripfluoperazine Hydrochloride
• 10H-Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-
• Stelazine (*Dihydrochloride*)
• UNII-214IZI85K3
• 10-[3-(4-METHYL-PIPERAZIN-1-YL)-PROPYL]-2-TRIFLUOROMETHYL-10H-PHENOTHIAZINE
• SKF 5019
• CHEBI:45951
• 214IZI85K3
• 2-Trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazine
• NCI17474
• Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-
• NSC-46061
• RP-7623
• Trifluoroperazine dihydrochloride
• Stelazine (TN)
• NSC17474
• TRIFLUOPERAZINE [INN]
• Stellazine
• Triftazine
• Triphtazin
• Triphtazine
• Novo-Trifluzine
• MLS001146870
• MLS002702821
• 2-Trifluoromethyl-10-[3'-(1-methyl-4-piperazinyl)propyl]phenothiazine
• 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-10H-phenothiazine
• 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-phenothiazine
• 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine dihydrochloride
• 10H-Phenothiazine,10-[3-[4-(methyl-d3)-1-piperazinyl]propyl]-2-(trifluoromethyl)-
• SMR001566649
• CAS-440-17-5
• Triperazina
• Flurazina
• Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-
• Terfluzine (TN)
• Eskazinyl (TN)
• Jatroneural (TN)
• Eskazine (TN)
• Modalina (TN)
• PMS Trifluoperazine
• Trifluoperaz (TN)
• Synklor (Salt/Mix)
• Stelazine (Salt/Mix)
• Triftazin (Salt/Mix)
• Spectrum_000668
• Terfluzine (Salt/Mix)
• Triftazine (Salt/Mix)
• Jatroneural (Salt/Mix)
• Fluoperazine (Salt/Mix)
• Triphthazine (Salt/Mix)
• Prestwick0_000313
• Prestwick1_000313
• Prestwick2_000313
• Prestwick3_000313
• Spectrum2_000828
• Spectrum3_001374
• Spectrum4_000368
• Spectrum5_001553
• Lopac-T-8516
• Biomol-NT_000060
• CHEMBL422
• D0R4OM
• cid_5566
• NCIStruc1_001127
• NCIStruc2_001093
• TRIFLUOPERAZINE [MI]
• BIDD:PXR0132
• Lopac0_001232
• SCHEMBL24866
• BSPBio_000306
• BSPBio_001190
• BSPBio_002928
• GTPL214
• KBioGR_000530
• KBioGR_000835
• KBioGR_002431
• KBioSS_000530
• KBioSS_001148
• KBioSS_002437
• MLS006011857
• DivK1c_000843
• TRIFLUOPERAZINE [HSDB]
• SPBio_000755
• SPBio_002525
• TRIFLUOPERAZINE [VANDF]
• BPBio1_000338
• BPBio1_001345
• DTXSID1046928
• TRIFLUOPERAZINE [WHO-DD]
• BDBM79181
• cid_2913535
• KBio1_000843
• KBio2_000530
• KBio2_001148
• KBio2_002431
• KBio2_003098
• KBio2_003716
• KBio2_004999
• KBio2_005666
• KBio2_006284
• KBio2_007567
• KBio3_000959
• KBio3_000960
• KBio3_002148
• KBio3_002910
• cMAP_000048
• NINDS_000843
• Bio1_000458
• Bio1_000947
• Bio1_001436
• Bio2_000435
• Bio2_000915
• HMS1362L11
• HMS1792L11
• HMS1990L11
• HMS2089J11
• HMS3429O07
• KUC109776N
• BCP32898
• EX-A3330
• C21-H24-F3-N3-S
• CCG-37306
• NCGC00013226
• PDSP1_001300
• PDSP2_001284
• s5856
• STK182873
• AKOS001487920
• DB00831
• SDCCGSBI-0051199.P005
• IDI1_000843
• IDI1_002190
• KSC-210-031
• MRF-0000088
• QTL1_000085
• NCGC00013226-02
• NCGC00013226-03
• NCGC00013226-04
• NCGC00013226-05
• NCGC00013226-06
• NCGC00013226-07
• NCGC00013226-08
• NCGC00013226-09
• NCGC00013226-10
• NCGC00013226-11
• NCGC00013226-12
• NCGC00013226-13
• NCGC00013226-15
• NCGC00013226-26
• NCGC00024251-03
• NCGC00024251-04
• NCGC00024251-05
• NCGC00024251-06
• NCGC00024251-07
• AC-35814
• NCI60_001427
• NCI60_004087
• SBI-0051199.P003
• LS-105595
• AB00053558
• FT-0650159
• C07168
• D08636
• EN300-708763
• 2-(((4-chlorophenyl)sulfonyl)amino)-benzoicaci
• AB00053558-27
• AB00053558_28
• AB00053558_29
• L001075
• Q1752915
• SR-01000003020-6
• BRD-K89732114-001-02-6
• BRD-K89732114-001-03-4
• BRD-K89732114-001-05-9
• BRD-K89732114-300-05-5
• BRD-K89732114-300-07-1
• Triphthazine;Trifluperazine;NSC-17474;RP-7623;SKF-5019
• 10-(.gamma.-(N'-Methylpiperazino)propyl)-2-trifluoromethylphenothiozine
• 2-Trifluoromethyl-10-[3''''-(1-methyl-4-piperazinyl)propyl]phenothiazine
• 2-trifluorometil-10-[3'-(1-metil-4-piperazinil), propil] fenotiazina
• Fenotiazina, 10-[3-(4-metil-1-piperazinil) propil]-2-(trifluorometil)-
• 10-[3-(4-Methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazine #
• 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)phenothiazine;hydrochloride
• 10-[3-(4-methylpiperazino)propyl]-2-(trifluoromethyl)phenothiazine;hydrochloride
• 10H-Fenotiazina, 10-[3-(4-metil-1-piperazinil) propil]-2-(trifluorometil)-
• 10H-Phenothiazine, 10-[3-(4-methyl-1-piperazinyl) propyl]-2-(trifluoromethyl)-
• Phenothiazine 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-(6CI8CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9845	98.45%
Caco-2	+	0.5910	59.10%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Lysosomes	0.5122	51.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9581	95.81%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9902	99.02%
P-glycoprotein inhibitior	+	0.9512	95.12%
P-glycoprotein substrate	+	0.9343	93.43%
CYP3A4 substrate	-	0.5707	57.07%
CYP2C9 substrate	+	0.6071	60.71%
CYP2D6 substrate	+	0.6593	65.93%
CYP3A4 inhibition	-	0.5618	56.18%
CYP2C9 inhibition	-	0.9144	91.44%
CYP2C19 inhibition	+	0.8995	89.95%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.7800	78.00%
CYP inhibitory promiscuity	+	0.8247	82.47%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9118	91.18%
Carcinogenicity (trinary)	Non-required	0.7197	71.97%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9387	93.87%
Skin irritation	-	0.7119	71.19%
Skin corrosion	-	0.9169	91.69%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9845	98.45%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8277	82.77%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8735	87.35%
Acute Oral Toxicity (c)	III	0.5358	53.58%
Estrogen receptor binding	-	0.6511	65.11%
Androgen receptor binding	-	0.5505	55.05%
Thyroid receptor binding	+	0.6794	67.94%
Glucocorticoid receptor binding	-	0.7382	73.82%
Aromatase binding	-	0.4841	48.41%
PPAR gamma	+	0.8249	82.49%
Honey bee toxicity	-	0.9656	96.56%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9848	98.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4931	Q15125	3-beta-hydroxysteroid-delta(8),delta(7)-isomerase	8 nM; 8 nM	Ki; Ki	via Super-PRED; PMID: 18955522
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	PMID: 23210623
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	19952.6 nM	Potency	PMID: 17243726
CHEMBL4096	P04637	Cellular tumor antigen p53	15848.9 nM; 19952.6 nM	Potency; Potency	PMID: 16180822; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	1000 nM; 630.96 nM	AC50; AC50	via CMAUP; PMID: 22194678
CHEMBL3622	P33261	Cytochrome P450 2C19	12589.3 nM; 1995.3 nM; 7943.3 nM	Potency; Potency; Potency	PMID: 15711537; PMID: 18183025; via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	316.2 nM; 1995.3 nM; 1000 nM	Potency; Potency; Potency	PMID: 22206869; PMID: 19177635; PMID: 19943620
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 10000 nM; 10000 nM; 15848.9 nM	Potency; Potency; Potency; Potency	PMID: 21090801; PMID: 15387655; PMID: 18610999; PMID: 18779359
CHEMBL2362978	P43351	DNA repair protein RAD52 homolog	13000 nM	AC50	PMID: 20553004
CHEMBL2311238	Q9BY08	Emopamil-binding protein-like	3.9 nM; 3.9 nM	Ki; Ki	via Super-PRED; PMID: 18625771
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	199.5 nM; 199.5 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL240	Q12809	HERG	6226 nM	IC50	PMID: 19053514
CHEMBL4040	P28482	MAP kinase ERK2	25118.9 nM	Potency	DOI: 10.1007/s00044-011-9950-4
CHEMBL1293224	P10636	Microtubule-associated protein tau	1258.9 nM; 15848.9 nM; 35481.3 nM; 44668.4 nM	Potency; Potency; Potency; Potency	PMID: 8229009; PMID: 9249976; PMID: 25871261; PMID: 25856683
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	11220.2 nM; 11220.2 nM	Potency; Potency	PMID: 11754601; PMID: 25768703
CHEMBL4302	P08183	P-glycoprotein 1	6300 nM; 7200 nM	IC50; IC50	PMID: 15921411; PMID: 25233084
CHEMBL1293235	P02545	Prelamin-A/C	11220.2 nM	Potency	DOI: 10.6019/CHEMBL1201861
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	16481.6 nM; 16481.6 nM	Potency; Potency	PMID: 23964644; via CMAUP
CHEMBL287	Q99720	Sigma opioid receptor	15 nM	Ki	PMID: 18183025
CHEMBL1293232	Q16637	Survival motor neuron protein	31622.8 nM	Potency	PMID: 19674906
CHEMBL1293256	P40225	Thrombopoietin	15848.9 nM; 15848.9 nM	Potency; Potency	PMID: 23398362; PMID: 19459643
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31622.8 nM	Potency	PMID: 21051535

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.54%	89.76%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.58%	96.09%
CHEMBL2073	P07947	Tyrosine-protein kinase YES	98.18%	83.14%
CHEMBL2581	P07339	Cathepsin D	97.43%	98.95%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	97.34%	93.65%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	96.55%	89.62%
CHEMBL217	P14416	Dopamine D2 receptor	94.69%	95.62%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	94.60%	81.29%
CHEMBL228	P31645	Serotonin transporter	94.33%	95.51%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	94.27%	85.83%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.97%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.02%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.57%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.02%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	86.37%	100.00%
CHEMBL4208	P20618	Proteasome component C5	85.48%	90.00%
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	85.14%	92.17%
CHEMBL234	P35462	Dopamine D3 receptor	84.59%	90.48%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.83%	82.69%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.49%	93.40%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.26%	94.62%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	81.85%	91.43%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.59%	90.71%
CHEMBL255	P29275	Adenosine A2b receptor	81.08%	98.59%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.27%	90.24%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	80.20%	92.50%

Plants that contains it

• Crotalaria pallida
• Crotalaria sericea

Cross-Links

• PubChem: 5566
• NPASS: NPC473417
• ChEMBL: CHEMBL422
• LOTUS: LTS0156745
• wikiData: Q1752915