Identification
- Generic Name
- Triflupromazine
- DrugBank Accession Number
- DB00508
- Background
A phenothiazine used as an antipsychotic agent and as an antiemetic.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Triflupromazine (DB00508)
- Weight
- Average: 352.417
Monoisotopic: 352.122103923 - Chemical Formula
- C18H19F3N2S
- Synonyms
- 10-(3-(Dimethylamino)propyl)-2-(trifluoromethyl)phenothiazine
- 2-(Trifluoromethyl)promazine
- 2-Trifluoromethyl-10-(gamma-dimethylaminopropyl)phenothiazine
- Fluopromazine
- Triflupromazin
- Triflupromazina
- Triflupromazine
- Triflupromazinum
- External IDs
- MC 4703
- SKF 4648-A
Pharmacology
- Indication
Used mainly in the management of psychoses. Also used to control nausea and vomiting.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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 (5HT2B).
Target Actions Organism ADopamine D2 receptor antagonistHumans ADopamine D1 receptor antagonistHumans A5-hydroxytryptamine receptor 2B antagonistHumans AMuscarinic acetylcholine receptor M1 antagonistHumans AMuscarinic acetylcholine receptor M2 antagonistHumans - Absorption
Absorption may be erratic and peak plasma concentrations show large interindividual differences.
- Volume of distribution
Not Available
- Protein binding
Very high (90% or more).
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Triflupromazine is combined with 1,2-Benzodiazepine. Acebutolol The serum concentration of Acebutolol can be increased when it is combined with Triflupromazine. Acenocoumarol The risk or severity of adverse effects can be increased when Triflupromazine is combined with Acenocoumarol. Acetazolamide The risk or severity of CNS depression can be increased when Triflupromazine is combined with Acetazolamide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Triflupromazine. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Triflupromazine hydrochloride 9E75N4A5HM 1098-60-8 FTNWXGFYRHWUKG-UHFFFAOYSA-N - International/Other Brands
- Vesprin (Bristol Myers Squibb)
Categories
- ATC Codes
- N05AA05 — Triflupromazine
- Drug Categories
- Agents producing tachycardia
- Anticholinergic Agents
- Antidepressive Agents
- Antiemetics
- Antipsychotic Agents
- Autonomic Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cholinesterase Inhibitors
- Dopamine Agents
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Gastrointestinal Agents
- Heterocyclic Compounds, Fused-Ring
- Muscarinic Antagonists
- Nervous System
- Neurotoxic agents
- Neurotransmitter Agents
- P-glycoprotein inhibitors
- Peripheral Nervous System Agents
- Phenothiazines
- Phenothiazines With Aliphatic Side-Chain
- Psycholeptics
- Psychotropic Drugs
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Sulfur Compounds
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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
- Alkyldiarylamines / Diarylthioethers / Benzenoids / 1,4-thiazines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organofluorides / Hydrocarbon derivatives / Alkyl fluorides
- Substituents
- Alkyl fluoride / Alkyl halide / Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Diarylthioether / Hydrocarbon derivative
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- phenothiazines, organofluorine compound, tertiary amine (CHEBI:9711)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- RO16TQF95Y
- CAS number
- 146-54-3
- InChI Key
- XSCGXQMFQXDFCW-UHFFFAOYSA-N
- 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
- IUPAC Name
- dimethyl({3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl})amine
- SMILES
- CN(C)CCCN1C2=CC=CC=C2SC2=C1C=C(C=C2)C(F)(F)F
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014650
- KEGG Drug
- D00390
- PubChem Compound
- 5568
- PubChem Substance
- 46507344
- ChemSpider
- 5367
- BindingDB
- 67544
- 10805
- ChEBI
- 9711
- ChEMBL
- CHEMBL570
- ZINC
- ZINC000000538507
- Therapeutic Targets Database
- DAP000294
- PharmGKB
- PA451773
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Triflupromazine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 5.54 BIOBYTE (1995) logS -5.3 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.0018 mg/mL ALOGPS logP 4.95 ALOGPS logP 4.81 Chemaxon logS -5.3 ALOGPS pKa (Strongest Basic) 9.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 6.48 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 94.93 m3·mol-1 Chemaxon Polarizability 35.29 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9926 Blood Brain Barrier + 0.9839 Caco-2 permeable + 0.7847 P-glycoprotein substrate Substrate 0.7862 P-glycoprotein inhibitor I Inhibitor 0.8563 P-glycoprotein inhibitor II Inhibitor 0.8737 Renal organic cation transporter Inhibitor 0.6721 CYP450 2C9 substrate Non-substrate 0.7813 CYP450 2D6 substrate Substrate 0.5115 CYP450 3A4 substrate Substrate 0.5822 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9141 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.8156 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6166 Ames test Non AMES toxic 0.875 Carcinogenicity Non-carcinogens 0.9349 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 3.2485 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9849 hERG inhibition (predictor II) Inhibitor 0.8433
Spectra
- Mass Spec (NIST)
- Download (7.91 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.8031925 predictedDarkChem Lite v0.1.0 [M-H]- 172.08038 predictedDeepCCS 1.0 (2019) [M+H]+ 183.2553925 predictedDarkChem Lite v0.1.0 [M+H]+ 174.4384 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.3820925 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.84802 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- Curator comments
- This class of drugs binds to dopamine receptors overall with D2 receptors being the most targeted.
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Horn AS, Post ML, Kennard O: Dopamine receptor blockade and the neuroleptics, a crystallographic study. J Pharm Pharmacol. 1975 Aug;27(8):553-63. doi: 10.1111/j.2042-7158.1975.tb09506.x. [Article]
- Chokhawala K, Stevens L: Antipsychotic Medications . [Article]
- Creese I, Burt DR, Snyder SH: Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs. J Neuropsychiatry Clin Neurosci. 1996 Spring;8(2):223-6. doi: 10.1176/jnp.8.2.223. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- Curator comments
- This class of drugs binds to dopamine receptors overall, and D1 binding could be implicated.
- General Function
- G-protein coupled amine receptor activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
- Gene Name
- DRD1
- Uniprot ID
- P21728
- Uniprot Name
- D(1A) dopamine receptor
- Molecular Weight
- 49292.765 Da
References
- Creese I, Burt DR, Snyder SH: Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs. J Neuropsychiatry Clin Neurosci. 1996 Spring;8(2):223-6. doi: 10.1176/jnp.8.2.223. [Article]
- Chokhawala K, Stevens L: Antipsychotic Medications . [Article]
- Horn AS, Post ML, Kennard O: Dopamine receptor blockade and the neuroleptics, a crystallographic study. J Pharm Pharmacol. 1975 Aug;27(8):553-63. doi: 10.1111/j.2042-7158.1975.tb09506.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
- Gene Name
- HTR2B
- Uniprot ID
- P41595
- Uniprot Name
- 5-hydroxytryptamine receptor 2B
- Molecular Weight
- 54297.41 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Cooper M, Wyllie JH: Some properties of 5-hydroxytryptamine receptors in the hindquarters of the rat. Br J Pharmacol. 1979 Sep;67(1):79-85. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Snyder S, Greenberg D, Yamamura HI: Antischizophrenic drugs and brain cholinergic receptors. Affinity for muscarinic sites predicts extrapyramidal effects. Arch Gen Psychiatry. 1974 Jul;31(1):58-61. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein coupled acetylcholine receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Snyder S, Greenberg D, Yamamura HI: Antischizophrenic drugs and brain cholinergic receptors. Affinity for muscarinic sites predicts extrapyramidal effects. Arch Gen Psychiatry. 1974 Jul;31(1):58-61. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Identical protein binding
- Specific Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Muraoka S, Miura T: Inactivation of cholinesterase induced by chlorpromazine cation radicals. Pharmacol Toxicol. 2003 Feb;92(2):100-4. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Ibrahim S, Peggins J, Knapton A, Licht T, Aszalos A: Influence of antipsychotic, antiemetic, and Ca(2+) channel blocker drugs on the cellular accumulation of the anticancer drug daunorubicin: P-glycoprotein modulation. J Pharmacol Exp Ther. 2000 Dec;295(3):1276-83. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 07:00