Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00390)
Name
Mefenamic acid
Synonyms    Click to Show/Hide the Synonyms of This API
mefenamic acid; 61-68-7; Ponstel; 2-[(2,3-dimethylphenyl)amino]benzoic acid; Ponstan; Mephenamic acid; Parkemed; Coslan; Mefacit; Ponalar; Methenamic acid; 2-((2,3-Dimethylphenyl)amino)benzoic acid; Mephenaminic acid; Mefenaminsaeure; Bonabol; Lysalgo; Tanston; Vialidon; Bafameritin-M; Tamany Bonsan; Ponstan forte; Acide mefenamique; Namphen; Pontal; Mefanamic acid; Bafhameritin-M; 2-(2,3-Dimethylanilino)benzoic acid; CN-35355; Mefenacid; Ponstil; Ponstyl; N-2,3-Xylylanthranilic acid; N-(2,3-Xylyl)anthranilic acid; INF 3355; INF-3355; Acido mefenamico; Acidum mefenamicum; N-(2,3-Xylyl)-2-aminobenzoic acid; N-(2,3-Dimethylphenyl)anthranilic acid; AGN-1255; CI-473; CL 473; Benzoic acid, 2-[(2,3-dimethylphenyl)amino]-; Anthranilic acid, N-2,3-xylyl-; CN 35355; NSC 94437; 2-(2,3-dimethylphenylamino)benzoic acid; UNII-367589PJ2C; Anthranilic acid, N-(2,3-xylyl)-; Benzoic acid, 2-((2,3-dimethylphenyl)amino)-; CI 473; MFCD00051721; 2-Diphenylaminecarboxylic acid, 2',3'-dimethyl-; CHEMBL686; MLS000069709; CHEBI:6717; NSC94437; NSC-94437; 367589PJ2C; CAS-61-68-7; NCGC00016278-07; SMR000058188; DSSTox_CID_3243; Mefenaminsaeure [German]; DSSTox_RID_76938; DSSTox_GSID_23243; Ac. mefenamico [Italian]; Acide mefenamique [French]; Acide mefenamique [INN-French]; Acido mefenamico [INN-Spanish]; Acidum mefenamicum [INN-Latin]; 2-(2,3-Xylidino)benzoic Acid; HSDB 3115; SR-01000000216; EINECS 200-513-1; BRN 2216243; Prestwick_506; Mefenamic Acid,(S); Spectrum_000174; CPD000058188; Opera_ID_542; Mefenamic acid [USAN:USP:INN:BAN:JAN]; Prestwick0_000054; Prestwick1_000054; Prestwick2_000054; Prestwick3_000054; Spectrum2_001941; Spectrum3_001082; Spectrum4_001235; Spectrum5_001341; Benzoic acid, 2-(2,3-dimethylphenyl)amino-; Anthranilic acid,3-xylyl-; cid_4044; SCHEMBL3544; Oprea1_193889; BSPBio_000207; BSPBio_002724; KBioGR_001730; KBioSS_000654; MLS001074162; DivK1c_000298; SPECTRUM1501103; SPBio_002001; SPBio_002128; BPBio1_000229; F0850-6853; GTPL2593; SGCUT00005; WLN: QVR BMR B1 C1; DTXSID5023243; HMS500O20; KBio1_000298; KBio2_000654; KBio2_003222; KBio2_005790; KBio3_001944; ZINC20241; BRD8217; M01AG01; NINDS_000298; HMS1568K09; HMS1921D13; HMS2090B07; HMS2092B17; HMS2095K09; HMS2232P18; HMS3259M19; HMS3370K18; HMS3652A10; HMS3712K09; HMS3885O22; Pharmakon1600-01501103; Mefenamic acid (JP17/USP/INN); Mefenamic acid, analytical standard; ALBB-025759; BCP08499; BRD-8217; HY-B0574; to_000071; Tox21_110344; Tox21_301983; BBL003564; BDBM50134036; CCG-39434; NSC757834; SBB056999; STK666691; AKOS001025551; AKOS002388313; Benzoic acid,3-dimethylphenyl)amino]-; Tox21_110344_1; DB00784; J2.344B; MCULE-1031776135; NC00517; NSC-757834; IDI1_000298; SMP2_000141; 2-(2,3-Dimethylanilino)benzoic acid #; NCGC00016278-01; NCGC00016278-02; NCGC00016278-03; NCGC00016278-04; NCGC00016278-05; NCGC00016278-06; NCGC00016278-10; NCGC00022393-03; NCGC00022393-04; NCGC00022393-05; NCGC00255401-01; AC-11160; AK-72920; AS-12677; BR-72920; ST086740; SBI-0051636.P002; 2-(2,3-Dimethyl-phenylamino)-benzoic acid; AB0012318; 2-[(2,3-dimethylphenyl) amino]benzoic acid; 2-Diphenylaminecarboxylic acid,3'-dimethyl-; AB00052200; AM20060688; FT-0628184; SW196700-3; UNM000001233403; C02168; D00151; M-6454; AB00052200-17; AB00052200_18; AB00052200_19; A833367; Q284321; SR-01000000216-2; SR-01000000216-4; W-105113; BRD-K92778217-001-06-1; Z56755828; 2-(2,3-Dimethyl-phenylamino)-benzoic acid(Mefenamic acid); Mefenamic acid, European Pharmacopoeia (EP) Reference Standard; Mefenamic acid, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Dysmenorrhea ICD-11: GA34 [1]
PubChem CID
4044
Formula
C15H15NO2
Canonical SMILES
CC1=C(C(=CC=C1)NC2=CC=CC=C2C(=O)O)C
InChI
1S/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)
InChIKey
HYYBABOKPJLUIN-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=4044"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 241.28 Topological Polar Surface Area 49.3
XlogP 5.1 Complexity 292
Heavy Atom Count 18 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Mefenamic acid 250 mg capsule Click to Show/Hide the Full List of Formulation(s):          8 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Citric acid; Lactose; Sodium benzoate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Titanium dioxide; Fd&c red no. 3; Silicon dioxide; Gelatin; Glycerol monooleate
                   Dosage Form Oral Capsule
                   Company Sciele Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [4]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [5]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose; Sodium benzoate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Citric acid monohydrate; Titanium dioxide; Fd&c red no. 3; Silicon dioxide; Gelatin
                   Dosage Form Oral Capsule
                   Company Prasco
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [4]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [5]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose, unspecified form; Sodium benzoate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Citric acid monohydrate; Titanium dioxide; Fd&c red no. 3; Silicon dioxide; Gelatin, unspecified
                   Dosage Form Oral Capsule
                   Company Shionogi
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [4]
Sodium benzoate DIG Info Carbonic anhydrase II (Ki = 30000 nM) [5]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c yellow no. 6; Magnesium stearate; Ferrosoferric oxide; Potassium hydroxide; Propylene glycol; Titanium dioxide; Fd&c red no. 3; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Lupin Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [7]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Fd&c red no. 3; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Micro Labs
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [7]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [4]
             Drug Formulation 6 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Fd&c red no. 3; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Paddock Laboratories,
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [7]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [4]
             Drug Formulation 7 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Ferric oxide yellow; Propylene glycol; Titanium dioxide; Dimethicone; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Belcher Pharmaceuticals; Qualitest Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [7]
             Drug Formulation 8 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Butyl alcohol; Fd&c blue no. 2; Isopropyl alcohol; Ammonia; Ferric oxide yellow; Propylene glycol; Titanium dioxide; Alcohol; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Breckenridge Pharmaceutical; Solubiomix
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [4]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [8]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [7]
References
1 FDA label for approved mefenamic acid from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 PubChem BioAssay data set.
4 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
5 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
6 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
7 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
8 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.

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