Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00687)
Name
Tolmetin
Synonyms    Click to Show/Hide the Synonyms of This API
tolmetin; 26171-23-3; 1-Methyl-5-p-toluoylpyrrole-2-acetic acid; Tolectin; Tolmetine; Tolmetina [DCIT]; McN-2559; Tolmetina; Tolmetino; Tolmetinum; Tolmetine [INN-French]; Tolmetinum [INN-Latin]; Tolmetino [INN-Spanish]; 1H-Pyrrole-2-acetic acid, 1-methyl-5-(4-methylbenzoyl)-; MCN 2559; 2-(1-METHYL-5-(4-METHYLBENZOYL)-1H-PYRROL-2-YL)ACETIC ACID; 1-Methyl-5-(4-methylbenzoyl)-pyrrole-2-acetic acid; 5-(p-Toluoyl)-1-methylpyrrole-2-acetic acid; 2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetic acid; UNII-D8K2JPN18B; Acido 1-metil-5-(p-tolnil)-pirrol-2-acetico; 2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid; Pyrrole-2-acetic acid, 1-methyl-5-p-toluoyl-; CHEMBL1020; D8K2JPN18B; [1-Methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid; CHEBI:71941; 1-Methyl-5-p-toluoyl-pyrrole-2-acetic acid; HSDB 3403; Tolmetin (USAN/INN); McN-2559-21-98; EINECS 247-497-2; BRN 0485305; Tolmetin [USAN:INN:BAN]; 1-Methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetic acid; Acido 1-metil-5-(p-tolnil)-pirrol-2-acetico [Spanish]; PubChem15045; Spectrum_000935; Prestwick0_000856; Prestwick1_000856; Prestwick2_000856; Prestwick3_000856; Spectrum2_001205; Spectrum3_000603; Spectrum4_000359; Spectrum5_001194; SCHEMBL3150; Oprea1_869397; BSPBio_000871; BSPBio_002106; KBioGR_000797; KBioSS_001415; 5-22-06-00392 (Beilstein Handbook Reference); BIDD:GT0468; DivK1c_000213; SPBio_000990; SPBio_002792; BPBio1_000959; GTPL7311; ZINC2191; DTXSID2043951; KBio1_000213; KBio2_001415; KBio2_003983; KBio2_006551; KBio3_001606; NINDS_000213; HMS2090D06; HMS3886I03; BCP09085; ANW-52106; BDBM50295287; MFCD00599595; AKOS015850645; CCG-267033; CS-W008734; DB00500; GS-6529; IDI1_000213; NCGC00094796-03; BR-34409; SBI-0051537.P002; AB0023814; FT-0649942; FT-0675272; 1-methyl- 5-(p-toluoyl)pyrrole-2-acetic acid; C07149; D02355; S-3564; 171T233; A818238; 1-Methyl-5-(4-methylbenzoyl)pyrrole-2-acetic acid; J-504975; Q3992411; BRD-K82562631-236-02-0; BRD-K82562631-325-03-9; F6782-4251; [1-Methyl-5-(4-methyl-benzoyl)-1H-pyrrol-2-yl]-acetic acid; [1-Methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid #; 2-[1-methyl-5-(4-methylphenyl)carbonyl-pyrrol-2-yl]ethanoic acid; 2-[1-methyl-5-[(4-methylphenyl)-oxomethyl]-2-pyrrolyl]acetic acid; [1-Methyl-5-(4-methyl-benzoyl)-1H-pyrrol-2-yl]-acetic acid(tolmetin); 2-{1-methyl-5-[(4-methylphenyl)carbonyl]-1H-pyrrol-2-yl}acetic acid
Clinical Status
Approved
Disease Indication Rheumatoid arthritis ICD-11: FA20 [1]
PubChem CID
5509
Formula
C15H15NO3
Canonical SMILES
CC1=CC=C(C=C1)C(=O)C2=CC=C(N2C)CC(=O)O
InChI
1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)
InChIKey
UPSPUYADGBWSHF-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=5509"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 257.279 Topological Polar Surface Area 59.3
XlogP 2.8 Complexity 347
Heavy Atom Count 19 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Tolmetin 400 mg capsule Click to Show/Hide the Full List of Formulation(s):          3 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
Sodium lauryl sulfate; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Fd&c blue no. 2; Magnesium stearate; Ferrosoferric oxide; Propylene glycol; Titanium dioxide; Croscarmellose sodium; Silicon dioxide; Cellulose, microcrystalline; Gelatin; Shellac
                   Dosage Form Oral Capsule
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             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
Fd&c yellow no. 6; Magnesium stearate; Talc; Titanium dioxide; Fd&c red no. 3; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company Mutual Pharmaceutical
                   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) [3]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             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
Fd&c red no. 40; Magnesium stearate; Titanium dioxide; Silicon dioxide; Gelatin; Starch, corn
                   Dosage Form Oral Capsule
                   Company Teva Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Tolmetin 600 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 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
Sodium lauryl sulfate; Magnesium stearate; Ferric oxide yellow; Ferrosoferric oxide; Titanium dioxide; Triacetin; Crospovidone; Povidone; Cellulose, microcrystalline; Hypromelloses; Polydextrose; Polyethylene glycol; Starch, corn
                   Dosage Form Oral Tablet
                   Company Stat Rx USA
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             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
Sodium lauryl sulfate; Magnesium stearate; Ferric oxide yellow; Ferrosoferric oxide; Titanium dioxide; Triacetin; Crospovidone; Cellulose, microcrystalline; Hypromelloses; Polydextrose; Polyethylene glycols; Povidones; Starch, corn
                   Dosage Form Oral Tablet
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Tolmetin Sodium eq 600mg base tablet Click to Show/Hide the Full List of Formulation(s):          1 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
Cellulose; Silicon Dioxide; Crospovidone; Hydroxypropyl Methyl Cellulose; Magnesium Stearate; Polyethylene Glycol; Corn Starch; Titanium Dioxide; Fd&C Yellow No 6; D&C Yellow No 10
                   Dosage Form Tablet
                   Company Ortho Mcneil Janssen
                   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) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Pregelatinized starch DIG Info Multidrug resistance protein 1 (Protein expression downregulation) [5]
          Tolmetin Sodium eq 400mg base capsule Click to Show/Hide the Full List of Formulation(s):          1 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
Gelatin; Magnesium Stearate; Corn Starch; Talc; Fd&C Red No 3; Fd&C Yellow No 6; Titanium Dioxide
                   Dosage Form Capsule
                   Company Ortho Mcneil Janssen
                   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) [3]
Erythrosine sodium anhydrous DIG Info Multidrug resistance protein 3 (IC50 = 133000 nM) [7]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Pregelatinized starch DIG Info Multidrug resistance protein 1 (Protein expression downregulation) [5]
          Tolmetin 200 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 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
Magnesium stearate; Talc; Cellulose, microcrystalline; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Mutual Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved tolmetin from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 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.
4 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
6 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
7 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov; 136(1):216-41.

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