NP-MRD: Showing NP-Card for trifluoperazine (NP0249021)

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Record Information

Version

2.0

Created at

2022-09-07 11:28:13 UTC

Updated at

2022-09-07 11:28:13 UTC

NP-MRD ID

NP0249021

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trifluoperazine

Description

Trifluoperazine, also known as stelazine or triftazin, belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. As of 2014 there was no good evidence for a difference between trifluoperazine and placebo with respect to the risk of experiencing intensified symptoms over a 16-week period nor in reducing significant agitation or distress. The annual development rate of tardive dyskinesia may be as high as 4%. Brand names include Eskazinyl, Eskazine, Jatroneural, Modalina, Stelazine, Terfluzine, Trifluoperaz, Triftazin. Trifluoperazine is a drug which is used for the treatment of anxiety disorders, depressive symptoms secondary to anxiety and agitation. Trifluoperazine is a very strong basic compound (based on its pKa). Trifluoperazine is a potentially toxic compound. All antipsychotics can cause the rare and sometimes fatal neuroleptic malignant syndrome. trifluoperazine is found in Crotalaria assamica. trifluoperazine was first documented in 2001 (PMID: 11121417). It is of the phenothiazine chemical class (PMID: 14974020) (PMID: 15722405) (PMID: 19277699).

Structure

MOL 3D MOL SDF PDB SMILES InChI

831
  Mrv0541 02231215022D          

 28 31  0  0  0  0            999 V2000
    5.2216   -2.6666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7184   -0.2841    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -1.7097    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463   -0.5817    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.4578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.0169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    2.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1336   -0.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2 28  1  0  0  0  0
  3 28  1  0  0  0  0
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  5  8  1  0  0  0  0
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  6 12  1  0  0  0  0
  6 15  1  0  0  0  0
  7 14  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 11  1  0  0  0  0
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 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
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 17 21  2  0  0  0  0
 18 23  1  0  0  0  0
 19 24  2  0  0  0  0
 20 22  2  0  0  0  0
 21 26  1  0  0  0  0
 22 25  1  0  0  0  0
 22 28  1  0  0  0  0
 23 25  2  0  0  0  0
 24 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    5.9074    0.1649    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8329   -0.8183    0.0963 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1682   -0.6619   -1.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044    0.4239   -1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    0.2057   -0.0756 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9324    0.8270   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1002    0.2285   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2870    0.7839   -1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2839    1.8110    0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6000    3.0013    0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1625    2.9834    2.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0709    1.8539    1.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6494   -0.8356    1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354   -2.0552    1.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9961   -3.1126    0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393   -2.8795   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8153   -3.9918   -1.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958   -5.1755   -0.9983 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7954   -4.0373   -2.6266 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -3.6001   -2.3360 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -1.6288   -0.8729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7930   -0.5719   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5031   -0.7453    0.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9873   -0.8009    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9185    0.5403    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394    1.0151   -0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8374   -0.3718   -0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6661   -1.5904   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9119   -0.3505   -1.9413 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142    1.4214   -1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177    0.3661   -2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4361    0.6335    0.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0518    1.9361   -0.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -0.8723   -1.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390    0.4247   -2.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1746    1.8080   -1.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8214    0.2025   -2.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9529    3.0566   -0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1507    5.0383    0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6222    4.9841    2.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208    2.9168    3.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9053   -2.2201    2.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5003   -4.0483    0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247   -1.5392   -1.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9713   -0.5984    1.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2252   -1.7648    0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1577   -1.7550    1.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093    0.0151    1.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 26  2  0
 26 25  1  0
 25 20  2  0
 20 19  1  0
 19 18  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  5 27  1  0
 27 28  1  0
 28  2  1  0
 26  9  1  0
 15 10  1  0
 18 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 25 48  1  0
 19 47  1  0
 18 46  1  0
 27 49  1  0
 27 50  1  0
 28 51  1  0
 28 52  1  0
M  END

831
  Mrv0541 02231215022D          

 28 31  0  0  0  0            999 V2000
    5.2216   -2.6666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7184   -0.2841    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -1.7097    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8463   -0.5817    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.4578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    2.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.0169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    2.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -1.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -2.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1336   -0.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  2 28  1  0  0  0  0
  3 28  1  0  0  0  0
  4 28  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 15  1  0  0  0  0
  7 14  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
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 17 21  2  0  0  0  0
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 22 25  1  0  0  0  0
 22 28  1  0  0  0  0
 23 25  2  0  0  0  0
 24 27  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0249021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C21H24F3N3S

> <MOLECULAR_WEIGHT>
407.496

> <EXACT_MASS>
407.164303088

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
41.94441396365014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
4.655923626666667

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.389157008062217

> <JCHEM_POLAR_SURFACE_AREA>
9.72

> <JCHEM_REFRACTIVITY>
110.97530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trifluoperazine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 831                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.747  -4.978   0.000  0.00  0.00           S+0
HETATM    2  F   UNK     0      14.408  -0.530   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0      15.958  -3.191   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0      16.513  -1.086   0.000  0.00  0.00           F+0
HETATM    5  N   UNK     0       7.080   2.721   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.413   4.261   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.747  -1.898   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.080   4.261   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   1.951   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.414   1.951   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   5.031   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.413   2.721   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.414   0.412   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.747  -0.358   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   5.031   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.081  -2.668   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.414  -2.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.081  -4.208   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.414  -4.208   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.457  -1.845   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.037  -1.845   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.852  -2.636   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.457  -5.031   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.037  -5.031   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.852  -4.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.642  -2.636   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.642  -4.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.183  -1.861   0.000  0.00  0.00           C+0
CONECT    1   18   19                                                       
CONECT    2   28                                                            
CONECT    3   28                                                            
CONECT    4   28                                                            
CONECT    5    8    9   10                                                  
CONECT    6   11   12   15                                                  
CONECT    7   14   16   17                                                  
CONECT    8    5   11                                                       
CONECT    9    5   12                                                       
CONECT   10    5   13                                                       
CONECT   11    6    8                                                       
CONECT   12    6    9                                                       
CONECT   13   10   14                                                       
CONECT   14    7   13                                                       
CONECT   15    6                                                            
CONECT   16    7   18   20                                                  
CONECT   17    7   19   21                                                  
CONECT   18    1   16   23                                                  
CONECT   19    1   17   24                                                  
CONECT   20   16   22                                                       
CONECT   21   17   26                                                       
CONECT   22   20   25   28                                                  
CONECT   23   18   25                                                       
CONECT   24   19   27                                                       
CONECT   25   22   23                                                       
CONECT   26   21   27                                                       
CONECT   27   24   26                                                       
CONECT   28    2    3    4   22                                             
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
10-[3-(4-Methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10H-phenothiazine	ChEBI
10-[3-(4-METHYL-piperazin-1-yl)-propyl]-2-trifluoromethyl-10H-phenothiazine	ChEBI
Trifluoperazina	ChEBI
Trifluoperazinum	ChEBI
Trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazine	ChEBI
Trifluoroperazine	ChEBI
Trifluperazine	ChEBI
Apo-trifluoperazine	Kegg
Trifluoperazin	HMDB
Trifluoromethylperazine	HMDB
Trifluroperizine	HMDB
Rhone poulenc rorer brand OF trifluoperazine hydrochloride	HMDB
Rhone-poulenc rorer brand OF trifluoperazine hydrochloride	HMDB
Trifluoperazine HCL	HMDB
Allphar brand OF trifluoperazine hydrochloride	HMDB
Apotex brand OF trifluoperazine hydrochloride	HMDB
GlaxoSmithKline brand OF trifluoperazine hydrochloride	HMDB
Link brand OF trifluoperazine hydrochloride	HMDB
Psicofarma brand OF trifluoperazine hydrochloride	HMDB
SmithKline beecham brand OF trifluoperazine hydrochloride	HMDB
Stelazine	HMDB
Triftazin	HMDB
Apo trifluoperazine	HMDB
ApoTrifluoperazine	HMDB
Eskazine	HMDB
Flupazine	HMDB
Scios brand OF trifluoperazine hydrochloride	HMDB
Terfluzine	HMDB
Trifluoperazine hydrochloride	HMDB

Chemical Formula

C₂₁H₂₄F₃N₃S

Average Mass

407.4960 Da

Monoisotopic Mass

407.16430 Da

IUPAC Name

10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10H-phenothiazine

Traditional Name

trifluoperazine

CAS Registry Number

Not Available

SMILES

CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(C=C3)C(F)(F)F)CC1

InChI Identifier

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Crotalaria assamica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Aryl thioether
Tertiary aliphatic/aromatic amine
N-alkylpiperazine
N-methylpiperazine
Para-thiazine
1,4-diazinane
Piperazine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Thioether
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organofluoride
Organohalogen compound
Organopnictogen compound
Amine
Alkyl halide
Alkyl fluoride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:45951 )
organofluorine compound (CHEBI:45951 )
N-alkylpiperazine (CHEBI:45951 )
N-methylpiperazine (CHEBI:45951 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.87	ALOGPS
logP	4.66	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	8.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.72 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.98 m³·mol⁻¹	ChemAxon
Polarizability	41.94 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014969

DrugBank ID

DB00831

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5365

KEGG Compound ID

C07168

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trifluoperazine

METLIN ID

Not Available

PubChem Compound

5566

PDB ID

TFP

ChEBI ID

45951

Good Scents ID

Not Available

References

General References

Shin SY, Kim SY, Kim JH, Min DS, Ko J, Kang UG, Kim YS, Kwon TK, Han MY, Kim YH, Lee YH: Induction of early growth response-1 gene expression by calmodulin antagonist trifluoperazine through the activation of Elk-1 in human fibrosarcoma HT1080 cells. J Biol Chem. 2001 Mar 16;276(11):7797-805. doi: 10.1074/jbc.M009465200. Epub 2000 Dec 19. [PubMed:11121417 ]
Marques LO, Lima MS, Soares BG: Trifluoperazine for schizophrenia. Cochrane Database Syst Rev. 2004;2004(1):CD003545. doi: 10.1002/14651858.CD003545.pub2. [PubMed:14974020 ]
Choi SY, Koh YS, Jo SH: Inhibition of human ether-a-go-go-related gene K+ channel and IKr of guinea pig cardiomyocytes by antipsychotic drug trifluoperazine. J Pharmacol Exp Ther. 2005 May;313(2):888-95. doi: 10.1124/jpet.104.080853. Epub 2005 Feb 18. [PubMed:15722405 ]
Qin J, Zima AV, Porta M, Blatter LA, Fill M: Trifluoperazine: a rynodine receptor agonist. Pflugers Arch. 2009 Aug;458(4):643-51. doi: 10.1007/s00424-009-0658-y. Epub 2009 Mar 11. [PubMed:19277699 ]
LOTUS database [Link]

Showing NP-Card for trifluoperazine (NP0249021)

MOL for NP0249021 (trifluoperazine)

3D MOL for NP0249021 (trifluoperazine)

3D SDF for NP0249021 (trifluoperazine)

3D-SDF for NP0249021 (trifluoperazine)

PDB for NP0249021 (trifluoperazine)

3D PDB for NP0249021 (trifluoperazine)

SMILES for NP0249021 (trifluoperazine)

INCHI for NP0249021 (trifluoperazine)

Structure for NP0249021 (trifluoperazine)

3D Structure for NP0249021 (trifluoperazine)