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Chemistry

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Also known as: Fluopromazine, Trifluopromazine, Vesprin, 146-54-3, Adazine, Psyquil

Molecular Formula

C₁₈H₁₉F₃N₂S

Molecular Weight

352.4 g/mol

InChI Key

XSCGXQMFQXDFCW-UHFFFAOYSA-N

FDA UNII

RO16TQF95Y

A phenothiazine used as an antipsychotic agent and as an antiemetic.

1 2D Structure

Triflupromazine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,N-dimethyl-3-[2-(trifluoromethyl)phenothiazin-10-yl]propan-1-amine

2.1.2 InChI

InChI=1S/C18H19F3N2S/c1-22(2)10-5-11-23-14-6-3-4-7-16(14)24-17-9-8-13(12-15(17)23)18(19,20)21/h3-4,6-9,12H,5,10-11H2,1-2H3

2.1.3 InChI Key

XSCGXQMFQXDFCW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CCCN1C2=CC=CC=C2SC3=C1C=C(C=C3)C(F)(F)F

2.2 Other Identifiers

2.2.1 UNII

RO16TQF95Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fluopromazine

2. Siquil

3. Trifluopromazine

2.3.2 Depositor-Supplied Synonyms

1. Fluopromazine

2. Trifluopromazine

3. Vesprin

4. 146-54-3

5. Adazine

6. Psyquil

7. 2-(trifluoromethyl)promazine

8. Triflupromazina

9. Triflupromazinum

10. Psyquil; Siquil

11. 10h-phenothiazine-10-propanamine, N,n-dimethyl-2-(trifluoromethyl)-

12. N,n-dimethyl-3-[2-(trifluoromethyl)phenothiazin-10-yl]propan-1-amine

13. 2-trifluoromethyl-10-(gamma-dimethylaminopropyl)phenothiazine

14. 10-(3-(dimethylamino)propyl)-2-(trifluoromethyl)phenothiazine

15. Vesprin (tn)

16. Ro16tqf95y

17. Chebi:9711

18. 10-3-(dimethylamino)propyl-2-(trifluoromethyl)phenothiazine

19. Vetame

20. Trifluopromazine Hydrochloride

21. N,n-dimethyl-3-[2-(trifluoromethyl)-10h-phenothiazin-10-yl]propan-1-amine

22. Fluopromazine Monohydrochloride

23. Phenothiazine, 10-(3-(dimethylamino)propyl)-2-(trifluoromethyl)-

24. Triflupromazine [inn]

25. Triflupromazinum [inn-latin]

26. Triflupromazina [inn-spanish]

27. Dimethyl({3-[2-(trifluoromethyl)-10h-phenothiazin-10-yl]propyl})amine

28. Nsc14959

29. Nsc17473

30. Hsdb 3407

31. N,n-dimethyl-3-[2-(trifluoromethyl)phenothiazin-10-yl]propan-1-amine Hydrochloride

32. Einecs 205-673-6

33. Cas-1098-60-8

34. Unii-ro16tqf95y

35. Triflupromazine (usp/inn)

36. Triflupromazin

37. 10-[3-(dimethylamino)propyl]-2-(trifluoromethyl)phenothiazine

38. Phenothiazine, 10-[3-(dimethylamino)propyl]-2-(trifluoromethyl)-

39. Sr-01000000224-4

40. Triflupromazine [usp:inn:ban]

41. N,n-dimethyl-2-(trifluoromethyl)-10h-phenothiazine-10-propanamine

42. Spectrum_000095

43. Prestwick0_000053

44. Prestwick1_000053

45. Prestwick2_000053

46. Prestwick3_000053

47. Spectrum4_000741

48. Spectrum5_001282

49. Lopac-t-2896

50. Chembl570

51. Triflupromazine [mi]

52. Lopac0_001146

53. Schembl44085

54. Bspbio_000205

55. Bspbio_003444

56. Kbiogr_001062

57. Kbioss_000515

58. Cid_66069

59. Divk1c_000808

60. Triflupromazine [hsdb]

61. Spbio_002126

62. Triflupromazine [vandf]

63. Bpbio1_000227

64. Gtpl4330

65. Triflupromazine [mart.]

66. Dtxsid9023704

67. Triflupromazine [who-dd]

68. Bdbm67544

69. Kbio1_000808

70. Kbio2_000515

71. Kbio2_003083

72. Kbio2_005651

73. Ninds_000808

74. Zinc538507

75. Pdsp1_001344

76. Pdsp2_001328

77. Triflupromazine [orange Book]

78. N,n-dimethyl-3-(2-(trifluoromethyl)-10h-phenothiazin-10-yl)-1-propanamine

79. Ccg-205220

80. Db00508

81. Sdccgsbi-0051113.p004

82. Triflupromazine [usp Monograph]

83. Idi1_000808

84. Ncgc00016012-01

85. Ncgc00016012-02

86. Ncgc00016012-03

87. Ncgc00016012-04

88. Ncgc00016012-05

89. Ncgc00016012-06

90. Ncgc00016012-07

91. Ncgc00016012-08

92. Ncgc00016012-09

93. Ncgc00016012-16

94. Ncgc00024300-04

95. Ls-14640

96. Nci60_001029

97. Nci60_001426

98. Sbi-0051113.p003

99. Ab00053647

100. D00390

101. Ab00053647_16

102. Ab00053647_17

103. 146t543

104. L001149

105. Q510494

106. Brd-k63675182-003-14-5

107. Dimethyl-[3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl]amine;hydrochloride

108. N,n-dimethyl-3-[2-(trifluoromethyl)-10-phenothiazinyl]-1-propanamine;hydrochloride

109. N,n-dimethyl-3-[2-(trifluoromethyl)-10h-phenothiazin-10-yl]-1-propanamine #

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₉F₃N₂S
Molecular Weight	352.4 g/mol
XLogP3	5.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	352.12210427 g/mol
Monoisotopic Mass	352.12210427 g/mol
Topological Polar Surface Area	31.8 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	416
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)

THIS PHENOTHIAZINE IS EFFECTIVE IN MGMNT OF POSTOPERATIVE NAUSEA & VOMITING, RADIATION SICKNESS, & NAUSEA & VOMITING CAUSED BY TOXINS. /HYDROCHLORIDE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1104

TREATMENT OF ORG BRAIN SYNDROMES, BOTH CHRONIC & ACUTE, IS ANOTHER USE...USE... IN /TREATMENT OF/ MANIA & DEPRESSION HAS MET WITH SOME SUCCESS... ANXIETY IS CONSIDERED...INDICATION FOR USE... /PHENOTHIAZINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 173

PHENOTHIAZINES...FAVORABLY MODIFY PATHOGNOMONIC SYMPTOMS OF SCHIZOPHRENIA, THAT IS, THOUGHT DISORDER; BLUNTED AFFECT, WITHDRAWAL, & RETARDATION; & AUTISTIC BEHAVIOR & MANNERISMS. FAVORABLE CHANGES IN BELLIGERENCE, RESISTIVENESS, PERCEPTUAL DISTURBANCES, & PARANOID PROJECTION ALSO OCCUR... /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 Therapeutic Uses (Complete) data for TRIFLUPROMAZINE (6 total), please visit the HSDB record page.

4.2 Drug Warning

TRIFLUPROMAZINE PRODUCES LESS SEDATION THAN SOME OTHER PHENOTHIAZINES (EG, PROMAZINE), BUT IT PROLONGS POSTANESTHESIA SLEEPING TIME. EXTRAPYRAMIDAL REACTIONS HAVE BEEN OBSERVED FOLLOWING EVEN SINGLE DOSES OF THIS ALIPHATIC COMPD. /HYDROCHLORIDE/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1105

PHENOTHIAZINES ARE BEST UTILIZED IN CONTROL OF NAUSEA & VOMITING OF SHORT DURATION, SINCE WITH PROLONGED USE INCIDENCE OF MOST OF THEIR ADVERSE EFFECTS INCR. /PHENOTHIAZINES/

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 1062

...PRECAUTIONS SHOULD BE OBSERVED IN USE OF PHENOTHIAZINES FOR NAUSEA & VOMITING...BECAUSE THEY MAY MASK DIAGNOSTIC SYMPTOMS IN ACUTE SURGICAL CONDITIONS OR NEUROLOGICAL SYNDROMES. /PHENOTHIAZINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 166

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

For more Drug Warnings (Complete) data for TRIFLUPROMAZINE (8 total), please visit the HSDB record page.

4.3 Minimum/Potential Fatal Human Dose

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB). /HYDROCHLORIDE/

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-223

4.4 Drug Indication

Used mainly in the management of psychoses. Also used to control nausea and vomiting.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Triflupromazine is a member of a class of drugs called phenthiazines, which are dopamine D1/D2 receptor antagonists. Phenothiazines are used to treat serious mental and emotional disorders, including schizophrenia and other psychotic disorders. It reduces anxiety, emotional withdrawal, hallucinations, disorganized thoughts, blunted mood, and suspiciousness. Triflupromazine is used particularly to control violent behavior during acute episodes of psychotic disorders. It can also be used to control severe nausea and vomiting, severe hiccups, and moderate to severe pain in some hospitalized patients. Triflupromazine acts on the central nervous system.

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 ATC Code

N - Nervous system

N05 - Psycholeptics

N05A - Antipsychotics

N05AA - Phenothiazines with aliphatic side-chain

N05AA05 - Triflupromazine

5.4 Absorption, Distribution and Excretion

Absorption

Absorption may be erratic and peak plasma concentrations show large interindividual differences.

FATE OF SEVERAL (14)C QUATERNARY PHENOTHIAZINES, SUCH AS...TRIFLUPROMAZINE METHIODIDE...HAVE BEEN STUDIED IN RAT. ...MORE OF IP DOSE OF PHENOTHIAZINE WAS EXCRETED IN FECES (VIA BILE). WHERE EXAMINED, NO N-DEALKYLATION OF QUATERNARY NITROGEN WAS DETECTED. /METHIODIDE/

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 86

5.5 Metabolism/Metabolites

Hepatic.

...METAB...BY OXIDATIVE PROCESSES MEDIATED LARGELY BY HEPATIC MICROSOMAL & OTHER DRUG-METABOLIZING ENZYMES. CONJUGATION WITH GLUCURONIC ACID...PROMINENT ROUTE.../PRC: REACTIONS INCL HYDROXYLATION, DEMETHYLATION, SULFOXIDE FORMATION; METABOLIC ALTERATIONS IN SIDE CHAIN MAY ALSO OCCUR/. /PHENOTHIAZINES/

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 405

5.6 Mechanism of Action

Triflupromazine binds to the dopamine D1 and dopamine D2 receptors and inhibits their activity. The mechanism of the anti-emetic effect is due predominantly to blockage of the dopamine D2 neurotransmitter receptors in the chemoreceptor trigger zone (CTZ) and vomiting centre. Triflupromazine blocks the neurotransmitter dopamine and the vagus nerve in the gastrointestinal tract. Triflupromazine also binds the muscarinic acetylcholine receptors (M1 and M2) and the tryptamine D receptors (5HT_2B).

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

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

THERE IS AN ADENYLATE CYCLASE IN LIMBIC SYSTEM, AS WELL AS IN CAUDATE NUCLEUS, THAT IS SPECIFICALLY ACTIVATED BY DOPAMINE. ...ACTIVATION OF...ENZYME IS... BLOCKED BY...PHENOTHIAZINES. ...THERAPEUTIC EFFICACY & SIDE EFFECTS MAY RELATE TO INHIBITION OF DOPAMINE ACTIVATION OF ADENYLATE CYCLASE. /PHENOTHIAZINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 160

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