Drug
D0057 | Flufenamic Acid
M
M01AG03 Flufenamic acid
[M01AG] Fenamates
[M01A] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
[M01] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
[M] Musculoskeletal system
| Toxicity | Dose | Time | Species | Model | Method | Action | Positive criterion | Reference |
|---|---|---|---|---|---|---|---|---|
| TRANSMEMBRANE POTENTIAL | 129 | 24hr | rat | hepatocytes | tetramethylrhodamine ethyl ester (TMRE) | decrease | AC50 (μM) | 40 |
| PROTONOPHORIC UNCOUPLING | 278 | |||||||
| MEMBRANE POTENTIAL | 36.64±1.87 | human | qHTS-HepG2 | MMP assay | decrease | IC50 | 163 | |
| MEMBRANE POTENTIAL | 17.34 | human | HepG2 | MMP assay | decrease | IC50 | 163 | |
| MEMBRANE POTENTIAL | 14.45±4.99 | rat | hepatocytes | MMP assay | decrease | IC50 | 163 | |
| MEMBRANE POTENTIAL | 42.5 µM | 30 mins | mouse | liver mitochondria | Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) | decrease | EC20 | 36 |
| RESPIRATION | 1.7 µM | 60 mins | mouse | liver mitochondria | Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. | decrease | EC20 | 36 |
| RESPIRATION | ND | 60 mins | mouse | liver mitochondria | Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. | Negative | EC20 | 36 |
| STATE 2 RESPIRATION | 2.9 ± 0.3 | rat | isolated rat liver mitochondria | State 2 respiration ( 96-well plate format using a phosphorescent oxygen-sensitive probe MitoXpress) | inhibit | UC50 (nmol/mg mitochondrial protein) | 40 | |
| STATE 3 RESPIRATION | 100 nmol/mg mitochondrial protein | rat | isolated rat liver mitochondria | State 3 respiration ( 96-well plate format using a phosphorescent oxygen-sensitive probe MitoXpress) | Negative | IC50 (nmol/mg mitochondrial protein) | 40 | |
| LIPID METABOLISM | 146 | 24hr | rat | hepatocytes | LipidTox, for neutral lipid accumulation, to evaluate lipid content. | accumulation | AC50 (μM) | 40 |
| GLUTATHIONE METABOLISM | 79 | 24hr | rat | hepatocytes | glutathion depletion: cells were incubated with 50 μM monochlorobimane with 6 μg/ml Hoechst 33342 | AC50 (μM) | 40 | |
| SWELLING | > 200 µM | 30 mins | mouse | liver mitochondria | swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) | increase | EC20 | 36 |
| ROS PRODUCTION | NR | rat | hepatocytes | use CM-H2DCFDA to monitor reactive oxygen species | Negative | AC50 (μM) | 40 | |
| CYTOCHROME C RELEASE | 70 | 24hr | rat | hepatocytes | cytochrome c release (anti-cytochrome c antibody ) | induce | AC50 (μM) | 40 |
| ER STRESS-INDUCED | 68 | 24hr | rat | hepatocytes | DNA damage 153 induction (GADD153 antibodies) for ER-stress induced apoptosis | induce | AC50 (μM) | 40 |
| Target | Dose | Time | Species | Model | Method | Action | Positive criterion | Reference |
|---|---|---|---|---|---|---|---|---|
| NADH:ubiquinone reductase | 1.7 µM | 60 mins | mouse | liver mitochondria | Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. | inhibit | EC20 | 36 |
| Succinate dehydrogenase | ND | 60 mins | mouse | liver mitochondria | Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. | Negative | EC20 | 36 |
| Cytochrome c | > 200 µM | 30 mins | mouse | liver mitochondria | Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) | release | EC20 | 36 |
| Pictogram | Signal | Statements | Precautionary Statement Codes |
|---|---|---|---|
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Danger |
Aggregated GHS information provided by 58 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. Reported as not meeting GHS hazard criteria by 1 of 58 companies. For more detailed information, please visit ECHA C&L website Of the 8 notification(s) provided by 57 of 58 companies with hazard statement code(s): H301 (94.74%): Toxic if swallowed [Danger Acute toxicity, oral] H315 (96.49%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (96.49%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (24.56%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure Respiratory tract irritation] Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. |
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.) |
| 1bm7 | 2-((3-(Trifluoromethyl)phenyl)amino)benzoic acid | 2-((3-Trifluromethyl)phenyl)aminobenzoic acid |
| 2-(3-(trifluoromethyl)phenylamino)benzoic acid | 2-(3-Trifluoromethylanilino)benzoic Acid | 2-[(3-Trifluoromethylphenyl)amino]benzoic Acid |
| 2-[(3-Trifluromethyl)phenyl]aminobenzoic acid | 2-[3-(Trifluoromethyl)anilino]benzoic acid | 2-[3-(Trifluoromethyl)anilino]benzoic acid # |
| 2-[3-(trifluoromethyl)anilino]-benzoic acid | 2-[[3-(TRIFLUOROMETHYL)PHENYL]AMINO] BENZOIC ACID | 2-[[3-(Trifluoromethyl)phenyl]amino]benzoic acid |
| 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid | 3'-Trifluoromethyldiphenylamine-2-carboxylic acid | 3-14-00-00905 (Beilstein Handbook Reference) |
| 530-78-9 | 530F789 | 60GCX7Y6BH |
| A13333 | AB00052198 | AB00052198-14 |
| AB00052198_15 | ACMC-209l43 | AK143107 |
| AKOS000265536 | ANT-1 | ANW-31633 |
| Achless | Acide flufenamique | Acide flufenamique [INN-French] |
| Acido flufenamico | Acido flufenamico [INN-Spanish] | Acido flufenamico [Italian] |
| Acidum flufenamicum | Acidum flufenamicum [INN-Latin] | Ansatin |
| Anthranilic acid, N-(.alpha.,.alpha.,.alpha.-trifluoro-m-tolyl)- | Anthranilic acid, N-(alpha,alpha,alpha-trifluoro-m-tolyl)- | Anthranilic acid,.alpha.,.alpha.-trifluoro-m-tolyl)- |
| Arlef | Arlef (TN) | BBL001490 |
| BCBcMAP01_000039 | BDBM17636 | BPBio1_000205 |
| BRD-K44067360-001-06-3 | BRD-K44067360-001-16-2 | BRN 1996069 |
| BSPBio_000185 | BSPBio_001319 | BSPBio_002866 |
| Benzoic acid, 2-((3-(trifluoromethyl)phenyl)amino)- | Benzoic acid, 2-[[3-(trifluoromethyl)phenyl]amino]- | Bio1_000042 |
| Bio1_000531 | Bio1_001020 | Bio2_000039 |
| Bio2_000519 | C.I. 440 | C13038 |
| C14H10F3NO2 | CAS-530-78-9 | CBDivE_012649 |
| CBiol_001756 | CCG-40167 | CCRIS 5266 |
| CHEBI:42638 | CHEMBL23588 | CI 440 |
| CN-27,554 | CN-27544 | CN-27554 |
| CS-4811 | CTK8B1828 | D01581 |
| DB-052254 | DB02266 | DSSTox_CID_3063 |
| DSSTox_GSID_23063 | DSSTox_RID_76859 | DTXSID7023063 |
| DivK1c_000581 | EC 208-494-1 | EINECS 208-494-1 |
| F0909-0007 | FFA | FLF |
| FT-0603454 | Flufacid | Flufenamic acid (JAN/USAN/INN) |
| Flufenamic acid [USAN:INN:BAN:JAN] | Flufenamic acid, 97% | Flufenamic acid, analytical standard, for drug analysis |
| Flufenaminsaeure | Flufenaminsaeure [German] | Fluore-200 |
| Fluphenamic acid | Fullsafe | GTPL2447 |
| HMS1361B21 | HMS1568J07 | HMS1791B21 |
| HMS1921B21 | HMS1989B21 | HMS2089E07 |
| HMS2092B09 | HMS2095J07 | HMS2232G24 |
| HMS3371F01 | HMS3402B21 | HMS3652F06 |
| HMS3712J07 | HMS501N03 | HTS000643 |
| HY-B1221 | IDI1_000581 | IDI1_033789 |
| INF 1837 | INF-1837 | KBio1_000581 |
| KBio2_000039 | KBio2_001737 | KBio2_002267 |
| KBio2_002607 | KBio2_004305 | KBio2_004835 |
| KBio2_005175 | KBio2_006873 | KBio2_007403 |
| KBio3_000077 | KBio3_000078 | KBio3_002366 |
| KBio3_002747 | KBioGR_000039 | KBioGR_000424 |
| KBioGR_002267 | KBioSS_000039 | KBioSS_001737 |
| KBioSS_002268 | KS-000015VF | KS-1143 |
| KSC911Q2R | LPEPZBJOKDYZAD-UHFFFAOYSA-N | LS-20583 |
| Lanceat | M456 | MCULE-8606118307 |
| MFCD00002422 | MLS000028563 | MLS001148610 |
| Meralen | N-((m-Trifluoromethyl)phenyl)-2-aminobenzoic acid | N-(.alpha.,.alpha.,.alpha.-Trifluoro-m-tolyl)anthranilic acid |
| N-(.alpha.,.alpha.-Trifluoro-m-tolyl)anthranilic acid | N-(3-Trifluoromethylphenyl)-anthranilic acid | N-(3-Trifluoromethylphenyl)anthranilic acid |
| N-(3-Trifluoromethylphenyl)anthranilicAcid | N-(alpha,alpha,alpha-Trifluoro-m-tolyl)anthranilic acid | N-(m-Trifluoromethylphenyl)-2-aminobenzoic acid |
| N-[(3-Trifluoromethyl)phenyl]anthranilic acid | N-[(m-Trifluoromethyl)phenyl]-2-aminobenzoic acid | N-[3-(Trifluoromethyl)phenyl]anthranilic acid |
| N-[m-(Trifluoromethyl)phenyl]-2-aminobenzoic acid | NCGC00016490-01 | NCGC00016490-02 |
| NCGC00016490-03 | NCGC00016490-04 | NCGC00016490-05 |
| NCGC00016490-06 | NCGC00016490-07 | NCGC00016490-08 |
| NCGC00016490-09 | NCGC00016490-10 | NCGC00016490-12 |
| NCGC00023200-03 | NCGC00023200-04 | NCGC00023200-05 |
| NCGC00023200-06 | NCGC00023200-07 | NCGC00255175-01 |
| NE10194 | NINDS_000581 | NSC 219007 |
| NSC-219007 | NSC-757823 | NSC-82699 |
| NSC219007 | NSC757823 | NSC82699 |
| Nichisedan | Opera_ID_578 | Paraflu |
| Parlef | Parlif | Pharmakon1600-01501015 |
| Plostene | Prestwick0_000203 | Prestwick1_000203 |
| Prestwick2_000203 | Prestwick3_000203 | Prestwick_220 |
| Q416341 | RT-000369 | Reumajust A |
| Ristogen | SBB001140 | SBI-0051633.P002 |
| SC-17641 | SCHEMBL17497 | SMR000059027 |
| SPBio_000898 | SPBio_002106 | SPECTRUM1501015 |
| SR-01000000241 | SR-01000000241-2 | SR-01000000241-3 |
| ST026563 | ST24038963 | STK985630 |
| SW196528-3 | Saal-F | Sastridex |
| Spectrum2_000789 | Spectrum3_001273 | Spectrum4_000102 |
| Spectrum5_000686 | Spectrum_001257 | Surika |
| TVX 916 | Tecramine | Tox21_110452 |
| Tox21_110452_1 | Tox21_302111 | UNII-60GCX7Y6BH |
| UNM000001246003 | W-105772 | WLN: QVR BMR CXFFF |
| ZINC86535 | cMAP_000004 | flufenamic acid |
| flufenamic-acid | n-(a,a,a-trifluoro-m-tolyl)anthranilic acid | s4268 |
| DrugBank Name | Flufenamic Acid |
| DrugBank | DB02266 |
| CAS Number | 1977-00-0, 530-78-9 |
| PubChem Compound | 3371 |
| KEGG Compound ID | C13038 |
| KEGG Drug | D01581 |
| PubChem.Substance | 46507173 |
| ChEBI | 42638 |
| PharmGKB | PA166049190 |
| ChemSpider | 3254 |
| BindingDB | 17636.0 |
| HET | FLF |
1. Chan et al. (2005)