Basic information
- CAS
146-54-3- Standard SMILES
CN(C)CCCN1c2ccccc2Sc2ccc(C(F)(F)F)cc21- InChIKey
XSCGXQMFQXDFCW-UHFFFAOYSA-N- Molecular formula
- C18H19F3N2S
- Average molar mass
- 352.4 g/mol
- Monoisotopic mass
- 352.12210427
Overview
Triflupromazine is a member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position. It has a role as an anticoronaviral agent, a dopaminergic antagonist, an antiemetic and a first generation antipsychotic. It is a tertiary amine, an organofluorine compound and a member of phenothiazines. It derives from a hydride of a 10H-phenothiazine.
Names & identifiers
- Preferred name
- Triflupromazine
- IUPAC
- N,N-dimethyl-3-[2-(trifluoromethyl)phenothiazin-10-yl]propan-1-amine
- English name
- triflupromazine
- Molecular formula
- C18H19F3N2S
- Molecular weight
- 352.4170696
Names & synonyms
triflupromazineFluopromazineTrifluopromazine146-54-3VesprinPsyquilTriflupromazinaVetameTriflupromazinum2-(Trifluoromethyl)promazineNivoman10H-Phenothiazine-10-propanamine, N,N-dimethyl-2-(trifluoromethyl)-
Show more names
AdazineTRIFLUOROPROMAZINEtriflupromazine USP/EP/BPFluphenazine hydrochloride IHS Impurity Edimethyl(3-(2-trifluoromethylphenothiazin-10-yl)propyl)amine10-[3-(Dimethylamino)propyl]-2-(trifluoromethyl)-10H-phenothiazine
2-Trifluoromethyl-10-(gamma-dimethylaminopropyl)phenothiazine10-(3-(Dimethylamino)propyl)-2-(trifluoromethyl)phenothiazineRO16TQF95YDTXSID9023704dimethyl({3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl})amineN,N-Dimethyl-2-(trifluoromethyl)-10H-phenothiazine-10-propanamineCHEBI:9711Phenothiazine, 10-(3-(dimethylamino)propyl)-2-(trifluoromethyl)-
Database identifiers
- CAS
146-54-3- PubChem CID
- 5568
- DTXSID
DTXSID9023704- ChEMBL
CHEMBL570- ChEBI
CHEBI:9711- UNII
- RO16TQF95Y
- EC Number
- 205-673-6
- Nikkaji
- J2.957B
Properties
Computed structural properties
- XLogP
- 5.2
- Topological polar surface area
- 31.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 416
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Nervous system -> Antipsychotics
LogP
5.2
5.17
Color/FormVISCOUS, LIGHT AMBER-COLORED, LIQ, WHICH CRYSTALLIZES ON PROLONGED STANDING INTO LARGE IRREGULAR CRYSTALS
Solubility
SOL IN WATER, ALC, & ACETONE; INSOL IN ETHER /HCL/
PRACTICALLY INSOL IN WATER
1.80e-03 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Boiling Point176 °C @ 0.7 MM HG
Refractive IndexINDEX OF REFRACTION: 1.5780 @ 23 °C/D
Physical DescriptionSolid
Stability/Shelf LifeSOLN ARE SENSITIVE TO AIR & LIGHT /HYDROCHLORIDE/
Collision Cross Section174.51 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Other Experimental Properties
SLIGHT, CHARACTERISTIC ODOR; MELTS BETWEEN 170 & 178 °C /HYDROCHLORIDE/
PH OF 2% AQ SOLN 4.1, IF PH IS RAISED TO 6.4, PPT OF FREE BASE RESULTS /HYDROCHLORIDE/
WHITE TO PALE TAN, CRYSTALLINE POWDER /HYDROCHLORIDE/
CRYSTALS FROM XYLENE /HYDROCHLORIDE/
Physicochemical properties
- Melting point
- 25 °C · 25°C
- Boiling point
- 0.7 · bp0.7 176°; bp0.4 162-164°
- Density
- 1.2198 · 1.2198 (estimate)
- refractive index
- 23 · nD23 1.5780
- pka
- 9.41 · pKa 9.41(H2O (extrap) t = 24±1 I～0.002) (Uncertain)
- Water Solubility
- 1.762 mg/L · 1.762mg/L(24 ºC)
- FDA UNII
- 16 TQF95Y · RO16TQF95Y
- ATC code
- 5 AA05 · N05AA05
- Symbol(GHS)
- 8 · GHS08,GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H331-H311-H351
- Precautionary statements
- 264 · P264-P270-P301+P310-P321-P330-P405-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P280-P302+P352-P312-P322-P361-P363-P405-P501-P201-P202-P281-P308+P313-P405-P501
- Hazardous Substances Data
- 146 · 146-54-3(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - 10H-Phenothiazine-10-propanamine, N,N-dimethyl-2-(trifluoromethyl)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Toxicology
Interactions
...ANTIPSYCHOTIC DRUGS...MAY BLOCK ANTIHYPERTENSIVE EFFECTS OF GUANETHIDINE. PT BEING TREATED WITH PHENOTHIAZINES SHOULD BE ADVISED THAT THEIR SUSCEPTIBILITY TO ALCOHOL MAY BE INCR. /PHENOTHIAZINES/
ADDITIVE TO ACTION OF OTHER DEPRESSANTS & WILL POTENTIATE ANESTHETICS.
MAY INCR TOXICITY OF ORGANOPHOSPHORUS OR OTHER ACETYLCHOLINESTERASE INHIBITORS & PROCAINE. DO NOT USE EPINEPHRINE TO COMBAT ITS HYPOTENSIVE OR DEPRESSANT EFFECTS AS IT POTENTIATES THEM.
CONCURRENT ADMIN OF PHENOTHIAZINES & TRICYCLIC ANTIDEPRESSANTS MAY RESULT IN INCR IN SERUM LEVEL OF EITHER AGENT. /PHENOTHIAZINES/
For more Interactions (Complete) data for TRIFLUPROMAZINE (7 total), please visit the HSDB record page.
Exposure RoutesAbsorption may be erratic and peak plasma concentrations show large interindividual differences.
Toxicity Summary
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<sub>2B</sub>).
Signs and SymptomsSymptoms 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.
Human Toxicity Excerpts
MILD ELEVATION OF TEMP...IF...GIVEN PARENTERALLY. ...HYPOTHERMIA CAN OCCUR & MAY BE DUE BOTH TO ACTION ON HEAT-REGULATING CENTER & TO DIRECT PERIPHERAL VASODILATATION. SENSITIVITY & ADAPTATION TO ENVIRONMENTAL TEMP CHANGE ARE IMPAIRED...FATAL HYPERTHERMIA & HEAT STROKE ARE POSSIBLE COMPLICATIONS. /PHENOTHIAZINES/
...JAUNDICE FOLLOWING PHENOTHIAZINE ADMIN IS HYPERSENSITIVITY MANIFESTATION. ... LEUKOCYTOSIS, LEUKOPENIA, & EOSINOPHILIA OCCUR WITH PHENOTHIAZINE MEDICATION. /PHENOTHIAZINES/
...SKIN DISORDERS ARE ASSOC WITH USE OF PHENOTHIAZINES. FIRST IS HYPERSENSITIVITY REACTION THAT MAY BE URTICARIAL, MACULOPAPULAR, PETECHIAL, OR EDEMATOUS. ...PHOTOSENSITIVITY OCCURS... /PHENOTHIAZINES/
ABNORMAL PIGMENTATION INDUCED BY LONG-TERM ADMIN OF PHENOTHIAZINES IN HIGH DOSES TO CHRONIC SCHIZOPHRENICS HAS BEEN REPORTED. ... PIGMENTARY RETINOPATHY...MAY BE CLOSELY RELATED TOXIC EFFECT OF PHENOTHIAZINES... /PHENOTHIAZINES/
For more Human Toxicity Excerpts (Complete) data for TRIFLUPROMAZINE (9 total), please visit the HSDB record page.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity ExcerptsAVOID RAPID IV (MAY CAUSE SEVERE HYPOTENSION & CV COLLAPSE), & INTRAARTERIAL INJECTIONS (DISORIENTATION, CONVULSIONS, & DEATHS MAY OCCUR) ESP IN HORSES.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS08,GHS06
- Hazard statements
- H301-H331-H311-H351
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P280-P302+P352-P312-P322-P361-P363-P405-P501-P201-P202-P281-P308+P313-P405-P501
- Hazardous Substances Data
- 146-54-3(Hazardous Substances Data)
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Protein BindingVery high (90% or more).
Pharmacodynamics
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.
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<sub>2B</sub>).
...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/
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/
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/
Hepatic.
MeSH Pharmacological Classification
Drugs used to prevent NAUSEA or VOMITING.
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.
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.
Absorption, Distribution and Excretion
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/
Cellular LocationsMembrane
Uses & manufacturing
Uses
MEDICATION (VET)
MEDICATION
Used mainly in the management of psychoses. Also used to control nausea and vomiting.
Methods of ManufacturingYALE ET AL, J AM CHEM SOC 79, 4375 (1957); BRITISH PATENT 813,861 (1959 TO SK & F).
Formulations/Preparations
TABLET-10, 25, 50 MG; SYRUP-50 MG/5 ML; VIAL-10 MG/ML IN 10 ML; SYRINGE-10 MG/ML.
ORAL SUSPENSION NF: 50 MG/5 ML (HYDROCHLORIDE EQUIVALENT).
ADAZINE, FLUOMAZINA, FLUOROFEN, NIVOMAN, PSYQUIL, SIQUIL, VESPRAL, VESPRIN. /HYDROCHLORIDE/
Use ClassificationPharmaceuticals
Applications
UsesIn psychiatric practice, triflupromazine is used for psychomotor excitement in patients with schizophrenia for paranoid and manic-depressive conditions, and for neurosis.
UsesAntipsychotic.
Upstream & downstream products
Upstream raw materials
Suppliers8 total
北京华美互利生物化工010-56205725 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
Additional notes
DefinitionChEBI: A member of the class of phenothiazines that is 10H-phenothiazine having a trifluoromethyl subsitituent at the 2-position and a 3-(dimethylamino)propyl group at the N-10 position.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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