yingweiwo

Triflusal (UR1501)

Alias: UR-1501; Triflusal, Disgren,UR1501;UR 1501; Grendis, Aflen, Triflux
Cat No.:V1067 Purity: ≥98%
Triflusal (formerly UR1501; Disgren, Grendis, Aflen, Triflux),a platelet aggregation inhibitor and a salicylate analog, acts by irreversibly inhibiting the production of thromboxane-B2 in platelets via acetylating the enzyme COX-1/cycloxygenase-1.
Triflusal (UR1501)
Triflusal (UR1501) Chemical Structure CAS No.: 322-79-2
Product category: COX
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
25mg
50mg
100mg
250mg
500mg
1g
Other Sizes

Other Forms of Triflusal (UR1501):

  • Triflusal-d3
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Triflusal (formerly UR1501; Disgren, Grendis, Aflen, Triflux), a platelet aggregation inhibitor and a salicylate analog, acts by irreversibly inhibiting the production of thromboxane-B2 in platelets via acetylating the enzyme COX-1/cycloxygenase-1. The main metabolite of Triflusal is HTB, which preserves 6-keto-PGF1α synthesis in porcine aortic endothelial cells (PAEC) cells without a significant decline for up to 24 h even at the higher concentration. Triflusal at 10 mM, 100 mM and 1 M decreases LDH efflux in rat brain slices after anoxia/reoxygenation by 24%, 35% and 49% respectively. Triflusal also reduces inducible NO synthase activity by 18%, 21% and 30%.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

In vitro activity: The main Triflusal metabolite, HTB, preserves 6-keto-PGF1α synthesis in porcine aortic endothelial cells (PAEC) cells without a significant decline for up to 24 h even at the higher concentration. Triflusal at 10 mM, 100 mM and 1 M decreases LDH efflux in rat brain slices after anoxia/reoxygenation by 24%, 35% and 49% respectively. Triflusal also reduces inducible NO synthase activity by 18%, 21% and 30%.

ln Vivo
Triflusal (10 mg/kg i.v.) reduces platelet deposition on subendothelium-induced primary thrombus by about 68% in rabbits. Triflusal (10 mg/kg i.v.) reduces platelet deposition on a fresh thrombus formed over tunica media by about 48% in rabbits. Triflusal (40 mg/kg p.o.) reduces platelet deposition on a primary thrombus triggered by subendothelium and tunica media by 53% in rabbits. Triflusal (40 mg/kg p.o.) significantly reduces Cox-2 mRNA levels and protein levels without influence Cox-1 mRNA levels on the vascular wall in rabbits. Triflusal (600 mg/day for 5 days) results in an increase in NO production by neutrophils and an increase in endothelial nitric oxide synthase (eNOS) protein expression in neutrophils in healthy volunteers. Triflusal (300 mg, twice-daily orally) shows a more important increase in total walking distance and in pain-free walking distance over the basal values than those treated with placebo, together with an improvement of the symptomatology correlated with claudication in patients with chronic peripheral arteriopathy. Triflusal (300 mg, twice-daily orally) shows an increase in the peak-flow recorded through strain-gauge plethysmography in patients with chronic peripheral arteriopathy. Triflusal (30 mg/kg) strongly decreases iNOS immunolabeling at both survival times analyzed, attenuating iNOS immunoreactivity in astroglial cells and infiltrated neutrophils in rats. Triflusal (30 mg/kg) decreases neuronal and microglial COX-2 expression at 10 and 24 hours after lesion and microglial and astroglial expression of IL-1beta and TNF-alpha at 24 hours after lesion in rats.
Animal Protocol
10 mg/kg i.v.
Rabbits
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Absorbed in the small intestine with a bioavailability range from 83% to 100%. There is no significant difference between the absorption of the oral solution and capsule formulation. Triflusal displays a Cmax of 11.6 mcg/ml and a tmax of 0.88 h. The major metabolite of triflusal presents different pharmacokinetic properties by showing a Cmax and tmax of 92.7 mcg/ml and 4.96 h, respectively.
The elimination pathway of triflusal is primarily renal. Urine analysis has shown the presence of unchanged triflusal, HTB and the glycine conjugate of HTB.
The reported volume of distribution for triflusal is of 34L.
Renal clearance is 0.8 +/- 0.2L/h and 0.18 +/1 0.04L/h for triflusal and HTB, respectively.
Metabolism / Metabolites
In the liver, triflusal undergoes deacetylation, forming its main metabolite 2-OH-4-trifluoromethyl benzoic acid (HTB). This major metabolite seems to have marked antiplatelet properties in vitro.
Biological Half-Life
In the healthy human, the half-life is 0.5 +/- 0.1h, while that of HTB is 34.3 +/- 5.3h.
Toxicity/Toxicokinetics
Protein Binding
Triflusal binds almost completely to plasma proteins reaching a 99% of the administered dose.
References
J Thromb Haemost.2008 Aug;6(8):1385-92;Eur J Clin Invest.2000 Sep;30(9):811-7.
Additional Infomation
2-acetyloxy-4-(trifluoromethyl)benzoic acid is a member of salicylates, a carboxylic ester and a member of benzoic acids.
Triflusal is a 2-acetoxy-4-trifluoromethylbenzoic acid and it is an aspirin chemically-related molecule but not a derivative. The benefits of this agent are the lack of action over the arachidonic acid pathway, the driven production of nitric oxide and the increase of cyclic nucleotide concentration on endothelial cells. The latest translates into the expansion of peripheral blood vessels. It is very important as a secondary prevention of ischemic stroke by offering a lower risk of bleeding. It was developed by J. Uriach and Company and even though it is commercialized in different countries it is not approved by the FDA, EMA or HealthCanada.
Drug Indication
Triflusal is indicated as prophylaxis of thromboembolic disorders. It has been registered in Spain and in other countries of Europe, South America and South Korea for the prevention of Stroke and myocardial infarction.
Mechanism of Action
Triflusal is chemically related to acetylsalicylic acid (ASA) and irreversibly inhibits cycloxygenase-1 (COX-1) in platelets. Acetylation of the active group of COX-1 prevents the formation of thromboxane-B2 in platelets. However, it is unique because it spares the arachidonic acid metabolic pathway in endothelial cells. In addition, it favors the production of nitric oxide, a vasodilator.
Pharmacodynamics
Triflusal is an antithrombotic anticoagulant. It irreversibly inhibits the production of thromboxane-B2 in platelets by acetylating cycloxygenase-1. Triflusal affects many other targets such as NF kappa B, which is a gene expression regulatory factor for cycloxygenase-a and cytokines. Numerous studies comparing the efficacy and safety profile (i.e. systemic hemorrhage) between triflusal and acetylsalsylic acid has shown either no significant difference or a better effacy and safety profile for triflusal. Triflusal has been shown to protect cerebral tissue due to its inhibition of lipid peroxidation resulting from anoxia-reoxygenation.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H7F3O4
Molecular Weight
248.16
Exact Mass
248.029
CAS #
322-79-2
Related CAS #
Triflusal-d3;2748541-63-9
PubChem CID
9458
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
316.0±42.0 °C at 760 mmHg
Melting Point
115 °C
Flash Point
144.9±27.9 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.484
LogP
2.9
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
3
Heavy Atom Count
17
Complexity
313
Defined Atom Stereocenter Count
0
InChi Key
RMWVZGDJPAKBDE-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H7F3O4/c1-5(14)17-8-4-6(10(11,12)13)2-3-7(8)9(15)16/h2-4H,1H3,(H,15,16)
Chemical Name
2-acetyloxy-4-(trifluoromethyl)benzoic acid
Synonyms
UR-1501; Triflusal, Disgren,UR1501;UR 1501; Grendis, Aflen, Triflux
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO:50 mg/mL (201.5 mM)
Water:<1 mg/mL
Ethanol:50 mg/mL (201.5 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 3 mg/mL (12.09 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 3 mg/mL (12.09 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

View More

Solubility in Formulation 3: ≥ 3 mg/mL (12.09 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.0297 mL 20.1483 mL 40.2966 mL
5 mM 0.8059 mL 4.0297 mL 8.0593 mL
10 mM 0.4030 mL 2.0148 mL 4.0297 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
+
+
+

Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02904109 Completed Drug: Triflusal
Drug: Placebo
Healthy Prof. Dominique de Quervain, MD September 13, 2016 Phase 2
NCT02321852 Completed Drug: Triflusal
Drug: Placebo
Healthy Prof. Dominique de Quervain, MD January 2015 Phase 2
NCT01612273 Completed Drug: Triflusal
Drug: Aspirin
Vasospastic Syndrome Yonsei University April 2011 Phase 4
NCT01174693 Completed Drug: Triflusal
Drug: Clopidogrel
Cerebral Infarction Gangnam Severance Hospital March 2010 Phase 4
NCT02616497 Completed Drug: Aspirin
Drug: Triflusal
Atherothrombosis University of Ioannina September 2015 Phase 4
Contact Us