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Chemistry

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Also known as: Trifluperazine, 117-89-5, Trifluoroperazine, Flurazine, Trifluoperazin, Triflurin

Molecular Formula

C₂₁H₂₄F₃N₃S

Molecular Weight

407.5 g/mol

InChI Key

ZEWQUBUPAILYHI-UHFFFAOYSA-N

FDA UNII

214IZI85K3

A phenothiazine with actions similar to CHLORPROMAZINE. It is used as an antipsychotic and an antiemetic.

Trifluoperazine is a Phenothiazine.

1 2D Structure

Trifluoperazine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

ZEWQUBUPAILYHI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F

2.2 Other Identifiers

2.2.1 UNII

214IZI85K3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Apo Trifluoperazine

2. Apo-trifluoperazine

3. Apotrifluoperazine

4. Eskazine

5. Flupazine

6. Stelazine

7. Terfluzine

8. Trifluoperazine Hcl

9. Trifluoperazine Hydrochloride

10. Trifluoroperazine

11. Trifluperazine

12. Triftazin

2.3.2 Depositor-Supplied Synonyms

1. Trifluperazine

2. 117-89-5

3. Trifluoroperazine

4. Flurazine

5. Trifluoperazin

6. Triflurin

7. Triperazine

8. Trifluoperazina

9. Trifluoromethylperazine

10. Trifluoperazinum

11. Trifluroperizine

12. Apo-trifluoperazine

13. Eskazine

14. Rp 7623

15. Fluoperazine

16. 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine

17. Trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazine

18. 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)-10h-phenothiazine

19. Tfp

20. Nsc 17474

21. 10-(3-(4-methylpiperazin-1-yl)propyl)-2-(trifluoromethyl)-10h-phenothiazine

22. 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10h-phenothiazine

23. Calmazine

24. Trifluoperazine (inn)

25. 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)phenothiazine

26. 10h-phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-

27. Nsc-17474

28. 10-(gamma-(n'-methylpiperazino)propyl)-2-trifluoromethylphenothiazine

29. 10h-phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-

30. 10-[3-(4-methyl-piperazin-1-yl)-propyl]-2-trifluoromethyl-10h-phenothiazine

31. Skf 5019

32. Chebi:45951

33. 214izi85k3

34. 2-trifluoromethyl-10-(3'-(1-methyl-4-piperazinyl)propyl)phenothiazine

35. Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-

36. Nsc-46061

37. Rp-7623

38. Nsc17474

39. Trifluoperazina [italian]

40. Trifluoperazine [inn]

41. Trifluoperazine [inn:ban]

42. Trifluoperazinum [inn-latin]

43. Trifluoperazina [inn-spanish]

44. Mls001146870

45. Mls002702821

46. 2-trifluoromethyl-10-[3'-(1-methyl-4-piperazinyl)propyl]phenothiazine

47. 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-10h-phenothiazine

48. Smr001566649

49. Ccris 6994

50. Hsdb 3195

51. 10-[3-(4-methylpiperazin-1-yl)propyl]-2-(trifluoromethyl)phenothiazine Dihydrochloride

52. Cas-440-17-5

53. Einecs 204-219-4

54. Apo-trifluoperazine (tn)

55. Nsc 46061

56. Stelazine (*dihydrochloride*)

57. Unii-214izi85k3

58. Phenothiazine, 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-

59. Nci17474

60. Synklor (salt/mix)

61. Stelazine (salt/mix)

62. Triftazin (salt/mix)

63. Spectrum_000668

64. Terfluzine (salt/mix)

65. Triftazine (salt/mix)

66. Jatroneural (salt/mix)

67. Fluoperazine (salt/mix)

68. Triphthazine (salt/mix)

69. Prestwick0_000313

70. Prestwick1_000313

71. Prestwick2_000313

72. Prestwick3_000313

73. Spectrum2_000828

74. Spectrum3_001374

75. Spectrum4_000368

76. Spectrum5_001553

77. Lopac-t-8516

78. Biomol-nt_000060

79. Chembl422

80. Cid_5566

81. 2-(((4-chlorophenyl)sulfonyl)amino)-benzoicaci

82. Ncistruc1_001127

83. Ncistruc2_001093

84. Trifluoperazine [mi]

85. Bidd:pxr0132

86. Lopac0_001232

87. Schembl24866

88. Bspbio_000306

89. Bspbio_001190

90. Bspbio_002928

91. Gtpl214

92. Kbiogr_000530

93. Kbiogr_000835

94. Kbiogr_002431

95. Kbioss_000530

96. Kbioss_001148

97. Kbioss_002437

98. Mls006011857

99. Divk1c_000843

100. Trifluoperazine [hsdb]

101. Spbio_000755

102. Spbio_002525

103. Trifluoperazine [vandf]

104. Bpbio1_000338

105. Bpbio1_001345

106. Dtxsid1046928

107. Trifluoperazine [who-dd]

108. Bdbm79181

109. Cid_2913535

110. Kbio1_000843

111. Kbio2_000530

112. Kbio2_001148

113. Kbio2_002431

114. Kbio2_003098

115. Kbio2_003716

116. Kbio2_004999

117. Kbio2_005666

118. Kbio2_006284

119. Kbio2_007567

120. Kbio3_000959

121. Kbio3_000960

122. Kbio3_002148

123. Kbio3_002910

124. Cmap_000048

125. Ninds_000843

126. Bio1_000458

127. Bio1_000947

128. Bio1_001436

129. Bio2_000435

130. Bio2_000915

131. Hms1362l11

132. Hms1792l11

133. Hms1990l11

134. Hms2089j11

135. Hms3429o07

136. Kuc109776n

137. Bcp32898

138. Ex-a3330

139. Ccg-37306

140. Ncgc00013226

141. Pdsp1_001300

142. Pdsp2_001284

143. S5856

144. Stk182873

145. Zinc19418959

146. 10-(3-(4-methyl-1-piperazinyl)propyl)-2-(trifluoromethyl)-phenothiazine

147. Akos001487920

148. Db00831

149. Sdccgsbi-0051199.p005

150. Idi1_000843

151. Idi1_002190

152. Ksc-210-031

153. Mrf-0000088

154. Qtl1_000085

155. Ncgc00013226-02

156. Ncgc00013226-03

157. Ncgc00013226-04

158. Ncgc00013226-05

159. Ncgc00013226-06

160. Ncgc00013226-07

161. Ncgc00013226-08

162. Ncgc00013226-09

163. Ncgc00013226-10

164. Ncgc00013226-11

165. Ncgc00013226-12

166. Ncgc00013226-13

167. Ncgc00013226-15

168. Ncgc00013226-26

169. Ncgc00024251-03

170. Ncgc00024251-04

171. Ncgc00024251-05

172. Ncgc00024251-06

173. Ncgc00024251-07

174. Ac-35814

175. Nci60_001427

176. Nci60_004087

177. Sbi-0051199.p003

178. Ab00053558

179. Ft-0650159

180. C07168

181. D08636

182. Ab00053558-27

183. Ab00053558_28

184. Ab00053558_29

185. L001075

186. Q1752915

187. Sr-01000003020-6

188. Brd-k89732114-001-02-6

189. Brd-k89732114-001-03-4

190. Brd-k89732114-001-05-9

191. Brd-k89732114-300-05-5

192. Brd-k89732114-300-07-1

193. Triphthazine;trifluperazine;nsc-17474;rp-7623;skf-5019

194. 10-(.gamma.-(n'-methylpiperazino)propyl)-2-trifluoromethylphenothiozine

195. 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)-10h-phenothiazine #

196. 10-[3-(4-methyl-1-piperazinyl)propyl]-2-(trifluoromethyl)phenothiazine;hydrochloride

197. 10-[3-(4-methylpiperazino)propyl]-2-(trifluoromethyl)phenothiazine;hydrochloride

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₄F₃N₃S
Molecular Weight	407.5 g/mol
XLogP3	5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	407.16430344 g/mol
Monoisotopic Mass	407.16430344 g/mol
Topological Polar Surface Area	35 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	510
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Antiemetics; Antipsychotic Agents, Phenothiazine; Dopamine Antagonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

IN THE TREATMENT OF ACUTE PSYCHOSES, THE DOSE OF ANTIPSYCHOTIC DRUG IS INCREASED DURING THE FIRST FEW DAYS TO ACHIEVE CONTROL OF SYMPTOMS. THE DOSE IS THEN ADJUSTED DURING THE NEXT SEVERAL WEEKS AS THE PATIENT'S CONDITION WARRANTS. /PHENOTHIAZINES/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 418

The use of antipsychotic drugs in mania and depression has met with some success. /PHENOTHIAZINES/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 419

...TRIFLUOPERAZINE...REPORTED EFFECTIVE IN SEVERELY IMPAIRED AUTISTIC CHILDREN, & DIFFERENTIAL DIAGNOSIS OF THIS GROUP FROM SO-CALLED MINIMAL-BRAIN-DAMAGE (MBD) SYNDROME IN CHILDREN IS ESSENTIAL.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 174

For more Therapeutic Uses (Complete) data for TRIFLUOPERAZINE (10 total), please visit the HSDB record page.

4.2 Drug Warning

PHENOTHIAZINES SHOULD BE USED WITH EXTREME CAUTION, IF @ ALL, IN UNTREATED EPILEPTIC PT & IN PT UNDERGOING WITHDRAWAL FROM CENTRAL DEPRESSANT DRUGS SUCH AS ALCOHOL & BARBITURATES. /PHENOTHIAZINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 159

...FEW PT WITH ANGINA PECTORIS HAVE REPORTED INCR PAIN DURING THERAPY WITH TRIFLUOPERAZINE. THEREFORE, PT WITH ANGINA SHOULD BE OBSERVED CAREFULLY & DRUG WITHDRAWN IF UNFAVORABLE RESPONSE OCCURS. /HYDROCHLORIDE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 440

SAFE USE...DURING PREGNANCY HAS NOT BEEN ESTABLISHED WITH RESPECT TO POSSIBLE ADVERSE EFFECTS ON FETAL DEVELOPMENT. ...PHENOTHIAZINES... SHOULD BE USED WITH EXTREME CAUTION IN PT WITH HISTORY OF GLAUCOMA OR PROSTATIC HYPERTROPHY. /PHENOTHIAZINES/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1021

ROUTINE ADMIN OF ANTIPARKINSONISM AGENTS SHOULD BE AVOIDED WITH MOST ANTIPSYCHOTIC DRUG REGIMENS. /PHENOTHIAZINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 172

For more Drug Warnings (Complete) data for TRIFLUOPERAZINE (28 total), please visit the HSDB record page.

4.3 Minimum/Potential Fatal Human Dose

Lethal dose: 0.3-0.8 mg/dL /From table/

Gossel, T.A., J.D. Bricker. Principles of Clinical Toxicology. 3rd ed. New York, NY: Raven Press, Ltd., 1994., p. 422

4.4 Drug Indication

For the treatment of anxiety disorders, depressive symptoms secondary to anxiety and agitation.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Trifluoperazine is a trifluoro-methyl phenothiazine derivative intended for the management of schizophrenia and other psychotic disorders. Trifluoperazine has not been shown effective in the management of behaviorial complications in patients with mental retardation.

5.2 MeSH Pharmacological Classification

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

TRIFLUOPERAZINE

5.3.2 FDA UNII

214IZI85K3

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Phenothiazines

5.4 ATC Code

N - Nervous system

N05 - Psycholeptics

N05A - Antipsychotics

N05AB - Phenothiazines with piperazine structure

N05AB06 - Trifluoperazine

5.5 Absorption, Distribution and Excretion

ULTIMATE SOJOURN OF PHENOTHIAZINE DRUGS IN BODY IS EXCEEDINGLY LONG. /PHENOTHIAZINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 163

5.6 Metabolism/Metabolites

Hepatic.

AFTER CHRONIC ADMIN OF PIPERAZINE-SUBSTITUTED PHENOTHIAZINE DRUGS...TO RATS, TISSUES CONTAINED DRUG METABOLITES, IN WHICH PIPERAZINE RING FISSION BY MULTIPLE OXIDATIVE N-DEALKYLATION HAD OCCURRED TO GIVE SUBSTITUTED ETHYLENEDIAMINE. ...2-TRIFLUOROMETHYL ANALOGUE WAS FORMED SIMILARLY FROM TRIFLUPERAZINE.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 255

IN VIVO DEGRADATION OF PIPERAZINE RING OF TRIFLUOPERAZINE LEADS TO FORMATION OF GAMMA-(PHENOTHIAZINYL-10)-PROPYLAMINE & ITS RING SUBSTITUTED ANALOGS CF3- & CL-. SULFOXIDES OF THESE METABOLITES HAVE BEEN IDENTIFIED AS URINARY BIOTRANSFORMATION PRODUCTS IN RATS (CHRONIC).

PMID:4813348 BREYER ET AL; BIOCHEM PHARM 23: 313-322 (1974)

5.7 Biological Half-Life

10-20 hours

5.8 Mechanism of Action

Trifluoperazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.

...PHENOTHIAZINES, BLOCK DOPAMINE RECEPTORS & INCR TURNOVER RATE OF DOPAMINE IN CORPUS STRIATUM. INCR TURNOVER RATE IS BELIEVED TO BE RESULT OF NEURONAL FEEDBACK MECHANISM. ...OF IDENTIFIED DOPAMINERGIC NEURONS IN SUBSTANTIA NIGRA & VENTRAL TEGMENTAL AREAS. SPONTANEOUS FIRING OF THESE CELLS IS INCR... /PHENOTHIAZINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 159

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