Identification

Name
Triflusal
Accession Number
DB08814
Type
Small Molecule
Groups
Approved, Investigational
Description

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.[11] It is very important as a secondary prevention of ischemic stroke by offering a lower risk of bleeding.[12] 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.

Structure
Thumb
Synonyms
  • Triflusal
Categories
UNII
1Z0YFI05OO
CAS number
322-79-2
Weight
Average: 248.157
Monoisotopic: 248.029643194
Chemical Formula
C10H7F3O4
InChI Key
RMWVZGDJPAKBDE-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-(acetyloxy)-4-(trifluoromethyl)benzoic acid
SMILES
CC(=O)OC1=C(C=CC(=C1)C(F)(F)F)C(O)=O

Pharmacology

Indication

Triflusal is indicated as prophylaxis of thromboembolic disorders.[15] 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.[14]

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.[1]

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.[5]

TargetActionsOrganism
AProstaglandin G/H synthase 1
antagonist
Human
ANuclear factor NF-kappa-B p105 subunit
antagonist
Human
ANitric oxide synthase, inducible
agonist
Human
AcAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
antagonist
Human
Absorption

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.[2] 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.[13]

Volume of distribution

The reported volume of distribution for triflusal is of 34L.[13]

Protein binding

Triflusal binds almost completely to plasma proteins reaching a 99% of the administered dose.[L1186]

Metabolism

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.[14]

Route of elimination

The elimination pathway of triflusal is primarily renal. Urine analysis has shown the presence of unchanged triflusal, HTB and the glycine conjugate of HTB.[L1186]

Half life

In the healthy human, the half-life is 0.5 +/- 0.1h, while that of HTB is 34.3 +/- 5.3h.[L1186]

Clearance

Renal clearance is 0.8 +/- 0.2L/h and 0.18 +/1 0.04L/h for triflusal and HTB, respectively.[L1186]

Toxicity

There is the possibility of producing major systemic hemorrhages.[L1168]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbciximabTriflusal may increase the anticoagulant activities of Abciximab.Approved
AcenocoumarolTriflusal may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Triflusal is combined with Acetylsalicylic acid.Approved, Vet Approved
AloxiprinThe risk or severity of adverse effects can be increased when Triflusal is combined with Aloxiprin.Experimental
AlprostadilAlprostadil may increase the anticoagulant activities of Triflusal.Approved, Investigational
AlteplaseTriflusal may increase the anticoagulant activities of Alteplase.Approved
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Triflusal is combined with Aminosalicylic Acid.Approved
AnagrelideAnagrelide may increase the anticoagulant activities of Triflusal.Approved
AncrodTriflusal may increase the anticoagulant activities of Ancrod.Approved, Investigational
AndrographolideAndrographolide may increase the anticoagulant activities of Triflusal.Investigational
AnistreplaseTriflusal may increase the anticoagulant activities of Anistreplase.Approved
Antithrombin III humanTriflusal may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanThe risk or severity of adverse effects can be increased when Triflusal is combined with Apixaban.Approved
AprotininThe therapeutic efficacy of Triflusal can be decreased when used in combination with Aprotinin.Approved, Investigational, Withdrawn
ArdeparinTriflusal may increase the anticoagulant activities of Ardeparin.Approved, Investigational, Withdrawn
ArgatrobanTriflusal may increase the anticoagulant activities of Argatroban.Approved, Investigational
AstaxanthinTriflusal may increase the anticoagulant activities of Astaxanthin.Investigational
AzelastineAzelastine may increase the anticoagulant activities of Triflusal.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Triflusal is combined with Balsalazide.Approved, Investigational
BatroxobinTriflusal may increase the anticoagulant activities of Batroxobin.Experimental
BecaplerminTriflusal may increase the anticoagulant activities of Becaplermin.Approved, Investigational
BemiparinTriflusal may increase the anticoagulant activities of Bemiparin.Approved, Investigational
BeraprostBeraprost may increase the anticoagulant activities of Triflusal.Investigational
BivalirudinTriflusal may increase the anticoagulant activities of Bivalirudin.Approved, Investigational
BrinaseTriflusal may increase the anticoagulant activities of Brinase.Experimental
BuflomedilBuflomedil may increase the anticoagulant activities of Triflusal.Experimental
ButylphthalideButylphthalide may increase the anticoagulant activities of Triflusal.Investigational
CangrelorCangrelor may increase the anticoagulant activities of Triflusal.Approved
CaplacizumabTriflusal may increase the anticoagulant activities of Caplacizumab.Investigational
Carbaspirin calciumThe risk or severity of adverse effects can be increased when Triflusal is combined with Carbaspirin calcium.Experimental, Investigational
CertoparinTriflusal may increase the anticoagulant activities of Certoparin.Approved, Investigational
CilostazolCilostazol may increase the anticoagulant activities of Triflusal.Approved, Investigational
Citric AcidTriflusal may increase the anticoagulant activities of Citric Acid.Approved, Nutraceutical, Vet Approved
ClopidogrelClopidogrel may increase the anticoagulant activities of Triflusal.Approved
CloricromenTriflusal may increase the anticoagulant activities of Cloricromen.Experimental
ClorindioneTriflusal may increase the anticoagulant activities of Clorindione.Experimental
Collagenase clostridium histolyticumThe risk or severity of adverse effects can be increased when Triflusal is combined with Collagenase clostridium histolyticum.Approved, Investigational
Dabigatran etexilateTriflusal may increase the anticoagulant activities of Dabigatran etexilate.Approved
DalteparinTriflusal may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidTriflusal may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanTriflusal may increase the anticoagulant activities of Darexaban.Investigational
DasatinibDasatinib may increase the anticoagulant activities of Triflusal.Approved, Investigational
DefibrotideDefibrotide may increase the anticoagulant activities of Triflusal.Approved, Investigational
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Triflusal is combined with Deoxycholic Acid.Approved
DersalazineThe risk or severity of adverse effects can be increased when Triflusal is combined with Dersalazine.Investigational
DesirudinTriflusal may increase the anticoagulant activities of Desirudin.Approved
DesmoteplaseTriflusal may increase the anticoagulant activities of Desmoteplase.Investigational
DextranTriflusal may increase the anticoagulant activities of Dextran.Approved, Investigational, Vet Approved
DicoumarolTriflusal may increase the anticoagulant activities of Dicoumarol.Approved
DiflunisalThe risk or severity of adverse effects can be increased when Triflusal is combined with Diflunisal.Approved, Investigational
DiphenadioneTriflusal may increase the anticoagulant activities of Diphenadione.Experimental
DipyridamoleDipyridamole may increase the anticoagulant activities of Triflusal.Approved
DitazoleTriflusal may increase the anticoagulant activities of Ditazole.Approved, Withdrawn
Drotrecogin alfaTriflusal may increase the anticoagulant activities of Drotrecogin alfa.Approved, Investigational, Withdrawn
Edetic AcidTriflusal may increase the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanTriflusal may increase the anticoagulant activities of Edoxaban.Approved
EnoxaparinTriflusal may increase the anticoagulant activities of Enoxaparin.Approved
EpinastineEpinastine may increase the anticoagulant activities of Triflusal.Approved, Investigational
EplivanserinTriflusal may increase the anticoagulant activities of Eplivanserin.Investigational
eplivanserineeplivanserine may increase the anticoagulant activities of Triflusal.Investigational
EpoprostenolEpoprostenol may increase the anticoagulant activities of Triflusal.Approved
EptifibatideEptifibatide may increase the anticoagulant activities of Triflusal.Approved, Investigational
Ethyl biscoumacetateTriflusal may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
Ferulic acidTriflusal may increase the anticoagulant activities of Ferulic acid.Experimental
FibrinolysinTriflusal may increase the anticoagulant activities of Fibrinolysin.Investigational
FluindioneTriflusal may increase the anticoagulant activities of Fluindione.Approved, Investigational
FondaparinuxTriflusal may increase the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
GabexateTriflusal may increase the anticoagulant activities of Gabexate.Investigational
GlucosamineGlucosamine may increase the antiplatelet activities of Triflusal.Approved, Investigational
GuacetisalThe risk or severity of adverse effects can be increased when Triflusal is combined with Guacetisal.Experimental
Hemoglobin crosfumarilThe risk or severity of adverse effects can be increased when Triflusal is combined with Hemoglobin crosfumaril.Experimental
HeparinTriflusal may increase the anticoagulant activities of Heparin.Approved, Investigational
HigenamineTriflusal may increase the anticoagulant activities of Higenamine.Investigational
HydroxytyrosolHydroxytyrosol may increase the anticoagulant activities of Triflusal.Investigational
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Triflusal is combined with Ibritumomab tiuxetan.Approved, Investigational
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Triflusal.Approved
IbudilastIbudilast may increase the anticoagulant activities of Triflusal.Approved, Investigational
Icosapent ethylIcosapent ethyl may increase the anticoagulant activities of Triflusal.Approved, Investigational, Nutraceutical
IdraparinuxTriflusal may increase the anticoagulant activities of Idraparinux.Investigational
IfenprodilIfenprodil may increase the anticoagulant activities of Triflusal.Approved, Investigational, Withdrawn
IfetrobanIfetroban may increase the anticoagulant activities of Triflusal.Investigational
IloprostIloprost may increase the anticoagulant activities of Triflusal.Approved, Investigational
IndobufenTriflusal may increase the anticoagulant activities of Indobufen.Investigational
KetanserinKetanserin may increase the anticoagulant activities of Triflusal.Investigational
LepirudinTriflusal may increase the anticoagulant activities of Lepirudin.Approved
LetaxabanTriflusal may increase the anticoagulant activities of Letaxaban.Investigational
LimaprostThe risk or severity of adverse effects can be increased when Limaprost is combined with Triflusal.Approved, Investigational
LinsidomineLinsidomine may increase the anticoagulant activities of Triflusal.Experimental
MelagatranTriflusal may increase the anticoagulant activities of Melagatran.Experimental
MesalazineThe risk or severity of adverse effects can be increased when Triflusal is combined with Mesalazine.Approved
Methyl salicylateThe risk or severity of adverse effects can be increased when Triflusal is combined with Methyl salicylate.Approved, Vet Approved
MilrinoneMilrinone may increase the anticoagulant activities of Triflusal.Approved
NadroparinTriflusal may increase the anticoagulant activities of Nadroparin.Approved, Investigational
NafamostatTriflusal may increase the anticoagulant activities of Nafamostat.Approved, Investigational
NaftopidilNaftopidil may increase the anticoagulant activities of Triflusal.Investigational
NimesulideNimesulide may increase the anticoagulant activities of Triflusal.Approved, Investigational, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Triflusal is combined with Nitroaspirin.Investigational
ObinutuzumabThe risk or severity of adverse effects can be increased when Triflusal is combined with Obinutuzumab.Approved, Investigational
OlsalazineThe risk or severity of adverse effects can be increased when Triflusal is combined with Olsalazine.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Triflusal.Approved, Nutraceutical
OtamixabanTriflusal may increase the anticoagulant activities of Otamixaban.Investigational
OzagrelTriflusal may increase the anticoagulant activities of Ozagrel.Investigational
ParnaparinTriflusal may increase the anticoagulant activities of Parnaparin.Approved, Investigational
Pentaerythritol TetranitrateTriflusal may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Triflusal.Approved
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Triflusal.Approved, Investigational
PhenindioneTriflusal may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonTriflusal may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Phenyl aminosalicylateThe risk or severity of adverse effects can be increased when Triflusal is combined with Phenyl aminosalicylate.Approved
PicotamideTriflusal may increase the anticoagulant activities of Picotamide.Experimental
Potassium CitrateTriflusal may increase the anticoagulant activities of Potassium Citrate.Approved, Investigational, Vet Approved
PrasugrelPrasugrel may increase the anticoagulant activities of Triflusal.Approved
Protein CTriflusal may increase the anticoagulant activities of Protein C.Approved
Protein S humanTriflusal may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeTriflusal may increase the anticoagulant activities of Protocatechualdehyde.Approved
RamatrobanRamatroban may increase the anticoagulant activities of Triflusal.Investigational
RelcovaptanRelcovaptan may increase the anticoagulant activities of Triflusal.Investigational
ResveratrolResveratrol may increase the anticoagulant activities of Triflusal.Approved, Experimental, Investigational
ReteplaseTriflusal may increase the anticoagulant activities of Reteplase.Approved, Investigational
ReviparinTriflusal may increase the anticoagulant activities of Reviparin.Approved, Investigational
RidogrelRidogrel may increase the anticoagulant activities of Triflusal.Approved
RivaroxabanTriflusal may increase the anticoagulant activities of Rivaroxaban.Approved
RosiglitazoneTriflusal may increase the anticoagulant activities of Rosiglitazone.Approved, Investigational
Salicylic acidThe risk or severity of adverse effects can be increased when Triflusal is combined with Salicylic acid.Approved, Investigational, Vet Approved
SarpogrelateTriflusal may increase the anticoagulant activities of Sarpogrelate.Investigational
SaruplaseTriflusal may increase the anticoagulant activities of Saruplase.Experimental
SelexipagTriflusal may increase the anticoagulant activities of Selexipag.Approved
SevofluraneSevoflurane may increase the anticoagulant activities of Triflusal.Approved, Vet Approved
Sodium CitrateTriflusal may increase the anticoagulant activities of Sodium Citrate.Approved, Investigational
SRT501SRT501 may increase the anticoagulant activities of Triflusal.Investigational
StreptokinaseTriflusal may increase the anticoagulant activities of Streptokinase.Approved, Investigational
SulodexideTriflusal may increase the anticoagulant activities of Sulodexide.Approved, Investigational
TenecteplaseTriflusal may increase the anticoagulant activities of Tenecteplase.Approved
TesmilifeneTesmilifene may increase the anticoagulant activities of Triflusal.Investigational
TicagrelorTriflusal may increase the anticoagulant activities of Ticagrelor.Approved
TiclopidineTiclopidine may increase the anticoagulant activities of Triflusal.Approved
TinzaparinTriflusal may increase the anticoagulant activities of Tinzaparin.Approved
TioclomarolTriflusal may increase the anticoagulant activities of Tioclomarol.Experimental
TipranavirTipranavir may increase the antiplatelet activities of Triflusal.Approved, Investigational
TirofibanTirofiban may increase the anticoagulant activities of Triflusal.Approved
TositumomabThe risk or severity of adverse effects can be increased when Triflusal is combined with Tositumomab.Approved, Investigational
TranilastTranilast may increase the anticoagulant activities of Triflusal.Approved, Investigational
TrapidilTrapidil may increase the anticoagulant activities of Triflusal.Approved
TreprostinilTriflusal may increase the anticoagulant activities of Treprostinil.Approved, Investigational
Trolamine salicylateThe risk or severity of adverse effects can be increased when Triflusal is combined with Trolamine salicylate.Approved
TroxerutinTriflusal may increase the anticoagulant activities of Troxerutin.Investigational
UrokinaseTriflusal may increase the anticoagulant activities of Urokinase.Approved, Investigational, Withdrawn
Vitamin EVitamin E may increase the antiplatelet activities of Triflusal.Approved, Nutraceutical, Vet Approved
VorapaxarVorapaxar may increase the anticoagulant activities of Triflusal.Approved
WarfarinTriflusal may increase the anticoagulant activities of Warfarin.Approved
XimelagatranTriflusal may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
Food Interactions
  • Gingko bilboa
  • Herbs with anticoagulant/antiplatelet activity such as alfalfa, feverfew, ginger, ginseng, grape seed, green tea, horseradish

References

General References
  1. Anninos H, Andrikopoulos G, Pastromas S, Sakellariou D, Theodorakis G, Vardas P: Triflusal: an old drug in modern antiplatelet therapy. Review of its action, use, safety and effectiveness. Hellenic J Cardiol. 2009 May-Jun;50(3):199-207. [PubMed:19465361]
  2. Izquierdo I, Borja J, Rovira S, Pelagio P, Torres F, Cebrecos J, Garcia-Rafanell J: Comparative bioavailability study of triflusal oral solution vs. triflusal capsules in healthy subjects. A single, randomized, two-way cross-over, open-label phase I study. Arzneimittelforschung. 2010;60(1):36-41. doi: 10.1055/s-0031-1296246. [PubMed:20184225]
  3. Duran X, Sanchez S, Vilahur G, Badimon L: Protective effects of triflusal on secondary thrombus growth and vascular cyclooxygenase-2. J Thromb Haemost. 2008 Aug;6(8):1385-92. doi: 10.1111/j.1538-7836.2008.03036.x. Epub 2008 May 22. [PubMed:18503633]
  4. Quetglas EG, Campanero MA, Sadaba B, Escolar M, Azanza JR: Bioequivalence of two oral formulations of triflusal capsules in healthy volunteers. Arzneimittelforschung. 2008;58(6):283-7. doi: 10.1055/s-0031-1296508. [PubMed:18677970]
  5. Gonzalez-Correa JA, De La Cruz JP: Triflusal: an antiplatelet drug with a neuroprotective effect? Cardiovasc Drug Rev. 2006 Spring;24(1):11-24. [PubMed:16939630]
  6. Fraj J, Valero A, Vives R, Perez I, Borja J, Izquierdo I, Picado C: Safety of triflusal (antiplatelet drug) in patients with aspirin-exacerbated respiratory diseases. Allergy. 2008 Jan;63(1):112-5. [PubMed:18053020]
  7. Sanchez-Machin I, Garcia Robaina JC, Torre Morin F: Widespread eczema from triflusal confirmed by patch testing. Contact Dermatitis. 2004 Apr;50(4):257. [PubMed:15186390]
  8. Matias-Guiu J, Ferro JM, Alvarez-Sabin J, Torres F, Jimenez MD, Lago A, Melo T: Comparison of triflusal and aspirin for prevention of vascular events in patients after cerebral infarction: the TACIP Study: a randomized, double-blind, multicenter trial. Stroke. 2003 Apr;34(4):840-8. Epub 2003 Mar 20. [PubMed:12649515]
  9. Culebras A, Rotta-Escalante R, Vila J, Dominguez R, Abiusi G, Famulari A, Rey R, Bauso-Tosselli L, Gori H, Ferrari J, Reich E: Triflusal vs aspirin for prevention of cerebral infarction: a randomized stroke study. Neurology. 2004 Apr 13;62(7):1073-80. [PubMed:15079004]
  10. Costa J, Ferro JM, Matias-Guiu J, Alvarez-Sabin J, Torres F: Triflusal for preventing serious vascular events in people at high risk. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD004296. [PubMed:16034926]
  11. Shin S, Kim KJ, Cho IJ, Hong GR, Jang Y, Chung N, Rah YM, Chang HJ: Effect of Triflusal on Primary Vascular Dysregulation Compared with Aspirin: A Double-Blind, Randomized, Crossover Trial. Yonsei Med J. 2015 Sep;56(5):1227-34. doi: 10.3349/ymj.2015.56.5.1227. [PubMed:26256964]
  12. Han SW, Kim YJ, Ahn SH, Seo WK, Yu S, Oh SH, Nam HS, Choi HY, Yoon SS, Kim SH, Lee JY, Lee JH, Hwang YH, Lee KO, Jung YH, Lee J, Sohn SI, Kim YN, Lee KA, Bushnell CD, Lee KY: Effects of Triflusal and Clopidogrel on the Secondary Prevention of Stroke Based on Cytochrome P450 2C19 Genotyping. J Stroke. 2017 Sep;19(3):356-364. doi: 10.5853/jos.2017.01249. Epub 2017 Sep 29. [PubMed:29037010]
  13. Ramis J, Mis R, Forn J, Torrent J, Gorina E, Jane F: Pharmacokinetics of triflusal and its main metabolite HTB in healthy subjects following a single oral dose. Eur J Drug Metab Pharmacokinet. 1991 Oct-Dec;16(4):269-73. [PubMed:1823870]
  14. Bogousslavsky J. (2001). Drug Therapy for Stroke Prevention. Taylor and Francis.
  15. MIMS [Link]
External Links
PubChem Compound
9458
PubChem Substance
347827803
ChemSpider
9086
ChEBI
94721
ChEMBL
CHEMBL1332032
Wikipedia
Triflusal
ATC Codes
B01AC18 — Triflusal
MSDS
Download (245 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedBasic ScienceHealthy Volunteers2
2CompletedTreatmentInsulin Resistance1
4CompletedHealth Services ResearchAtherothrombosis1
4CompletedTreatmentCerebral Infarctions1
4CompletedTreatmentVasospastic Syndrome1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)114-117ºC'MSDS'
water solubility<1 mg/ml'MSDS'
logP2.231'MSDS'
Predicted Properties
PropertyValueSource
Water Solubility0.696 mg/mLALOGPS
logP2.4ALOGPS
logP2.12ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.42 m3·mol-1ChemAxon
Polarizability19.32 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Acylsalicylic acids
Alternative Parents
Trifluoromethylbenzenes / Phenol esters / Benzoic acids / Phenoxy compounds / Benzoyl derivatives / Dicarboxylic acids and derivatives / Carboxylic acid esters / Carboxylic acids / Organofluorides / Organic oxides
show 3 more
Substituents
Acylsalicylic acid / Trifluoromethylbenzene / Phenol ester / Benzoic acid / Phenoxy compound / Benzoyl / Dicarboxylic acid or derivatives / Carboxylic acid ester / Carboxylic acid derivative / Carboxylic acid
show 10 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Anninos H, Andrikopoulos G, Pastromas S, Sakellariou D, Theodorakis G, Vardas P: Triflusal: an old drug in modern antiplatelet therapy. Review of its action, use, safety and effectiveness. Hellenic J Cardiol. 2009 May-Jun;50(3):199-207. [PubMed:19465361]
  2. Dominguez MJ, Vacas M, Saez Y, Olabarria I, Velasco A, Iriarte JA, Forn J: Effects of triflusal in patients with prosthetic heart valves. Clin Ther. 1985;7(3):357-60. [PubMed:3838919]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Transcriptional repressor activity, rna polymerase ii transcription regulatory region sequence-specific binding
Specific Function
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...
Gene Name
NFKB1
Uniprot ID
P19838
Uniprot Name
Nuclear factor NF-kappa-B p105 subunit
Molecular Weight
105355.175 Da
References
  1. Zhang W, Potrovita I, Tarabin V, Herrmann O, Beer V, Weih F, Schneider A, Schwaninger M: Neuronal activation of NF-kappaB contributes to cell death in cerebral ischemia. J Cereb Blood Flow Metab. 2005 Jan;25(1):30-40. [PubMed:15678110]
  2. Anninos H, Andrikopoulos G, Pastromas S, Sakellariou D, Theodorakis G, Vardas P: Triflusal: an old drug in modern antiplatelet therapy. Review of its action, use, safety and effectiveness. Hellenic J Cardiol. 2009 May-Jun;50(3):199-207. [PubMed:19465361]
  3. Gomez-Isla T, Blesa R, Boada M, Clarimon J, Del Ser T, Domenech G, Ferro JM, Gomez-Anson B, Manubens JM, Martinez-Lage JM, Munoz D, Pena-Casanova J, Torres F: A randomized, double-blind, placebo controlled-trial of triflusal in mild cognitive impairment: the TRIMCI study. Alzheimer Dis Assoc Disord. 2008 Jan-Mar;22(1):21-9. doi: 10.1097/WAD.0b013e3181611024. [PubMed:18317243]
  4. Whitehead SN, Bayona NA, Cheng G, Allen GV, Hachinski VC, Cechetto DF: Effects of triflusal and aspirin in a rat model of cerebral ischemia. Stroke. 2007 Feb;38(2):381-7. Epub 2006 Dec 28. [PubMed:17194886]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 Da
References
  1. Anninos H, Andrikopoulos G, Pastromas S, Sakellariou D, Theodorakis G, Vardas P: Triflusal: an old drug in modern antiplatelet therapy. Review of its action, use, safety and effectiveness. Hellenic J Cardiol. 2009 May-Jun;50(3):199-207. [PubMed:19465361]
  2. Sanchez de Miguel L, Casado S, Farre J, Garcia-Duran M, Rico LA, Monton M, Romero J, Bellver T, Sierra MP, Guerra JI, Mata P, Esteban A, Lopez-Farre A: Comparison of in vitro effects of triflusal and acetysalicylic acid on nitric oxide synthesis by human neutrophils. Eur J Pharmacol. 1998 Feb 5;343(1):57-65. [PubMed:9551715]
  3. De Miguel LS, Jimenez A, Monton M, Farre J, Del Mar Arriero M, Rodriguez-Feo JA, Garcia-Canete J, Rico L, Gomez J, Nunez A, Casado S, Farre AL: A 4-trifluoromethyl derivative of salicylate, triflusal, stimulates nitric oxide production by human neutrophils: role in platelet function. Eur J Clin Invest. 2000 Sep;30(9):811-7. [PubMed:10998082]
  4. Gonzalez-Correa JA, De La Cruz JP: Triflusal: an antiplatelet drug with a neuroprotective effect? Cardiovasc Drug Rev. 2006 Spring;24(1):11-24. [PubMed:16939630]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Metal ion binding
Specific Function
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. Can hydrolyze both cAMP and cGMP, but has higher affinity for cAMP and is more efficient wit...
Gene Name
PDE10A
Uniprot ID
Q9Y233
Uniprot Name
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
Molecular Weight
88411.71 Da
References
  1. McNeely W, Goa KL: Triflusal. Drugs. 1998 Jun;55(6):823-33; discussion 834-5. [PubMed:9617597]
  2. De Miguel LS, Jimenez A, Monton M, Farre J, Del Mar Arriero M, Rodriguez-Feo JA, Garcia-Canete J, Rico L, Gomez J, Nunez A, Casado S, Farre AL: A 4-trifluoromethyl derivative of salicylate, triflusal, stimulates nitric oxide production by human neutrophils: role in platelet function. Eur J Clin Invest. 2000 Sep;30(9):811-7. [PubMed:10998082]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. JCcardiol [Link]

Drug created on June 28, 2011 23:05 / Updated on August 02, 2018 06:10