ContaminantDB: Trifluoperazine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (18)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:45 UTC

Update Date

2016-11-09 01:08:43 UTC

Accession Number

CHEM002283

Identification

Common Name

Trifluoperazine

Class

Small Molecule

Description

Trifluoperazine is only found in individuals that have used or taken this drug. It is a phenothiazine with actions similar to chlorpromazine. It is used as an antipsychotic and an antiemetic. [PubChem]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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Antiemetic
Antipsychotic Agent
Dopamine Antagonist
Drug
Ether
Metabolite
Organic Compound
Organofluoride
Phenothiazine
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

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 Molecular Mass

407.496 g/mol

Monoisotopic Mass

407.164 g/mol

CAS Registry Number

117-89-5

IUPAC Name

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

Traditional Name

trifluoperazine

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	202-210°C at 6.00E-01 mm Hg
Solubility	12.2 mg/L (at 24°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.0088 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03kc-9730000000-49438d7f5a4236b51602	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-08mi-8921200000-2aff2d698385cab14cdb	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-9000100000-e2406a8adccd141c03e7	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03kc-9730000000-49438d7f5a4236b51602	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-08mi-8921200000-2aff2d698385cab14cdb	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-9000100000-e2406a8adccd141c03e7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0irv-9667000000-deccae3c053209941ea9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0000900000-a01e8dfa304983005945	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-0000900000-7b23271ee0eec105a7c5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-06r6-0900500000-0ea8c080e1d078157f50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03dl-1900000000-2608f082c54c542054e0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0229-8910000000-5b36d7157269ff6ba38c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0006-0901000000-06a3d20c96b187c19fad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-0110900000-8af3aa3c7acbf89b8b20	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0btc-1911400000-46dc3c49b2371e4bfb02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0102900000-c7f3c26a540bba469a6d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-3918600000-0425f149418e81474ddd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9623000000-d1310936305ee7ea664e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0001900000-ce43ff55b11825ac5096	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-0090200000-5c65bf0b372d774d4385	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-4390000000-7c7e77cb89eafbe85363	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000900000-100cfe5f7d72e7cb4519	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-0901800000-10b4b4fb7a8c235ad902	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c0r-9612100000-f822b67e0486f6cde009	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-93423d8802c27fe68345	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0026900000-7f5cdc5d710c6a312dc8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0193000000-421df1fba238d9cd5da6	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03kc-9740000000-e505b8906d154e2285a4	Spectrum

Toxicity Profile

Route of Exposure

Oral

Mechanism of Toxicity

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.

Metabolism

Hepatic. Half Life: 10-20 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include agitation, coma, convulsions, difficulty breathing, difficulty swallowing, dry mouth, extreme sleepiness, fever, intestinal blockage, irregular heart rate, low blood pressure, and restlessness.

Treatment

Treatment is essentially symptomatic and supportive. Early gastric lavage is helpful. Keep patient under observation and maintain an open airway, since involvement of the extrapyramidal mechanism may produce dysphagia and respiratory difficulty in severe overdosage. Do not attempt to induce emesis because a dystonic reaction of the head or neck may develop that could result in aspiration of vomitus. Extrapyramidal symptoms may be treated with anti-parkinsonism drugs, barbiturates or Benadryl. See prescribing information for these products. Care should be taken to avoid increasing respiratory depression. If administration of a stimulant is desirable, amphetamine, dextroamphetamine or caffeine with sodium benzoate is recommended. Stimulants that may cause convulsions (e.g., picrotoxin or pentylenetetrazol) should be avoided. If hypotension occurs, the standard measures for managing circulatory shock should be initiated. If it is desirable to administer a vasoconstrictor, Levophed and Neo-Synephrine are most suitable. Other pressor agents, including epinephrine, are not recommended because phenothiazine derivatives may reverse the usual elevating action of these agents and cause a further lowering of blood pressure. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB00831

HMDB ID

HMDB0014969

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID