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2021 MitoTox | (CC BY-NC 4.0)
Drug

D0078 | Mefenamic acid

Molecular Formula C15H15NO2
Molecular Weight 241.28
Structure
State solid
Clearance * Oral cl=21.23 L/hr [Healthy adults (18-45 yrs)]
Volume of distribution * 1.06 L/kg [Normal Healthy Adults (18-45 yr)]
Route of elimination The fecal route of elimination accounts for up to 20% of the dose, mainly in the form of unconjugated 3-carboxymefenamic acid.3 The elimination half-life of mefenamic acid is approximately two hours. Mefenamic acid, its metabolites and conjugates are primarily excreted by the kidneys. Both renal and hepatic excretion are significant pathways of elimination.
Protein binding 0.9
Half life 2 hours
Absorption Mefenamic acid is rapidly absorbed after oral administration.
Description anthranilic acid derivatives class of nonsteroidal anti-inflammatory drugs

M

M01AG01 Mefenamic 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 376 24hr rat hepatocytes tetramethylrhodamine ethyl ester (TMRE) decrease AC50 (μM) 40
MEMBRANE POTENTIAL 49.7 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 10.1 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 17.9 ± 2.2 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 161 24hr rat hepatocytes LipidTox, for neutral lipid accumulation, to evaluate lipid content. accumulation AC50 (μM) 40
GLUTATHIONE METABOLISM 148 24hr rat hepatocytes glutathion depletion: cells were incubated with 50 μM monochlorobimane with 6 μg/ml Hoechst 33342 AC50 (μM) 40
SWELLING > 400 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 277 24hr rat hepatocytes cytochrome c release (anti-cytochrome c antibody ) induce AC50 (μM) 40
ER STRESS-INDUCED 61 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 10.1 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
Warning

Aggregated GHS information provided by 125 companies from 5 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 125 companies. For more detailed information, please visit ECHA C&L website


Of the 4 notification(s) provided by 124 of 125 companies with hazard statement code(s):


H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]


H361 (24.19%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


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.


 P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]


H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H362: May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]


H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure]


H371: May cause damage to organs [Warning Specific target organ toxicity, single exposure]


H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


 P201, P202, P260, P263, P264, P270, P281, P301+P312, P307+P311, P308+P313, P309+P311, P314, P321, P330, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Body temperature increased

  • Diabetes mellitus

  • Dysmenorrhoea

  • Menorrhagia

  • Metrorrhagia

  • Pain

  • Toothache

    • 2-((2,3-Dimethylphenyl)amino)benzoic acid 2-(2,3-Dimethyl-phenylamino)-benzoic acid 2-(2,3-Dimethyl-phenylamino)-benzoic acid(Mefenamic acid)
    2-(2,3-Dimethylanilino)benzoic acid 2-(2,3-Dimethylanilino)benzoic acid # 2-(2,3-Xylidino)benzoic Acid
    2-(2,3-dimethylphenylamino)benzoic acid 2-Diphenylaminecarboxylic acid, 2',3'-dimethyl- 2-Diphenylaminecarboxylic acid,3'-dimethyl-
    2-[(2,3-dimethylphenyl) amino]benzoic acid 2-[(2,3-dimethylphenyl)amino]benzoic acid 367589PJ2C
    4-methyl-N-(3-{3-[(4-methylpiperidin-1-yl)carbonyl]imidazo[2,1-b][1,3]thiazol-6-yl}phenyl)benzenesulfonamide 61-68-7 A833367
    AB00052200 AB00052200-17 AB00052200_18
    AB00052200_19 AB0012318 AB1009470
    AC-11160 AGN-1255 AK-72920
    AKOS001025551 AKOS002388313 ALBB-025759
    AM20060688 AS-12677 Ac. mefenamico [Italian]
    Acide mefenamique Acide mefenamique [French] Acide mefenamique [INN-French]
    Acido mefenamico Acido mefenamico [INN-Spanish] Acidum mefenamicum
    Acidum mefenamicum [INN-Latin] Anthranilic acid, N-(2,3-xylyl)- Anthranilic acid, N-2,3-xylyl-
    Anthranilic acid,3-xylyl- BBL003564 BCP08499
    BDBM50134036 BPBio1_000229 BR-72920
    BRD-8217 BRD-K92778217-001-06-1 BRD8217
    BRN 2216243 BSPBio_000207 BSPBio_002724
    Bafameritin-M Bafhameritin-M Benzoic acid, 2-((2,3-dimethylphenyl)amino)-
    Benzoic acid, 2-(2,3-dimethylphenyl)amino- Benzoic acid, 2-[(2,3-dimethylphenyl)amino]- Benzoic acid,3-dimethylphenyl)amino]-
    Bonabol C02168 CAS-61-68-7
    CCG-39434 CHEBI:6717 CHEMBL686
    CI 473 CI 473 pound notCN-35355 CI-473
    CL 473 CN 35355 CN-35355
    CPD000058188 CS-2681 Coslan
    D00151 DB00784 DSSTox_CID_3243
    DSSTox_GSID_23243 DSSTox_RID_76938 DTXSID5023243
    DivK1c_000298 EINECS 200-513-1 F0850-6853
    FT-0628184 GTPL2593 HL 1
    HMS1568K09 HMS1921D13 HMS2090B07
    HMS2092B17 HMS2095K09 HMS2232P18
    HMS3259M19 HMS3370K18 HMS3652A10
    HMS3712K09 HMS500O20 HSDB 3115
    HY-B0574 HYYBABOKPJLUIN-UHFFFAOYSA-N IDI1_000298
    INF 3355 INF-3355 InChI=1/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18
    KBio1_000298 KBio2_000654 KBio2_003222
    KBio2_005790 KBio3_001944 KBioGR_001730
    KBioSS_000654 KS-00000WDA LS-20589
    Lysalgo M-6454 M1782
    MCULE-1031776135 MFCD00051721 MLS000069709
    MLS001074162 Mefacit Mefanamic acid
    Mefedolo Mefenacid Mefenamic Acid,(S)
    Mefenamic acid (JP17/USP/INN) Mefenamic acid [USAN:USP:INN:BAN:JAN] Mefenamic acid, European Pharmacopoeia (EP) Reference Standard
    Mefenamic acid, United States Pharmacopeia (USP) Reference Standard Mefenamic acid, analytical standard Mefenamicacid
    Mefenaminsaeure Mefenaminsaeure [German] Mefenaminsaure
    Mephenamic acid Mephenaminic acid Methenamic acid
    Mycasaal N-(2,3-Dimethylphenyl)anthranilic acid N-(2,3-Xylyl)-2-aminobenzoic acid
    N-(2,3-Xylyl)anthranilic acid N-2,3-Xylylanthranilic acid NC00517
    NCGC00016278-01 NCGC00016278-02 NCGC00016278-03
    NCGC00016278-04 NCGC00016278-05 NCGC00016278-06
    NCGC00016278-07 NCGC00016278-10 NCGC00022393-03
    NCGC00022393-04 NCGC00022393-05 NCGC00255401-01
    NINDS_000298 NSC 94437 NSC-757834
    NSC-94437 NSC757834 NSC94437
    Namphen Opera_ID_542 Oprea1_193889
    Parkemed Pharmakon1600-01501103 Ponalar
    Ponstan Ponstan forte Ponstel
    Ponstil Ponstyl Pontal
    Prestwick0_000054 Prestwick1_000054 Prestwick2_000054
    Prestwick3_000054 Prestwick_506 Q284321
    Rolan SAM002554908 SBB056999
    SBI-0051636.P002 SC-16204 SCHEMBL3544
    SGCUT00005 SMP2_000141 SMR000058188
    SPBio_002001 SPBio_002128 SPECTRUM1501103
    SR-01000000216 SR-01000000216-2 SR-01000000216-4
    ST086740 ST2409237 STK666691
    SW196700-3 Spectrum2_001941 Spectrum3_001082
    Spectrum4_001235 Spectrum5_001341 Spectrum_000174
    Tamany Bonsan Tanston Tox21_110344
    Tox21_110344_1 Tox21_301983 UNII-367589PJ2C
    UNM000001233403 Vialidon W-105113
    WLN: QVR BMR B1 C1 Z56755828 ZINC20241
    cid_4044 in-M mefenamic acid
    mefenamic-acid s4078 to_000071

    DrugBank Name Mefenamic acid
    DrugBank DB00784
    CAS Number 500996-04-3, 61-68-7
    PubChem Compound 4044
    KEGG Compound ID C02168
    KEGG Drug D00151
    PubChem.Substance 46505405
    ChEBI 6717
    PharmGKB PA450347
    ChemSpider 3904
    BindingDB 50134036.0
    TTD DAP000779
    Wikipedia Mefenamic_acid
    HET ID8
    DPD 10002

    1. Chan et al. (2005)
    2. Dykens et al. (2007)