Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00457)
Name
Naratriptan
Synonyms    Click to Show/Hide the Synonyms of This API
naratriptan; 121679-13-8; N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide; UNII-QX3KXL1ZA2; N-methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide; QX3KXL1ZA2; 1H-Indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-; CHEMBL1278; N-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamide; CHEBI:7478; Colatan; naratriptanum; Naramig (TN); Naratriptan (INN); NCGC00181786-01; Naratriptan [INN:BAN]; PubChem2191; GTPL45; SCHEMBL68753; BIDD:GT0312; ZINC4076; DTXSID7023354; HY-B0197; 2578AH; ABP000374; BDBM50073682; N-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]ethanesulfonamide; AKOS015895854; AC-5013; BCP9000978; DB00952; NCGC00181786-03; NCGC00181786-04; NCGC00181786-08; FT-0656760; A25336; C07792; D08255; AB01565792_02; L000432; Q421315; N-Methyl-3-(1-methyl-4 -piperidinyl)-1H-indole-5-ethansulphonamide; N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulphonamide; 2-[3-(1-Methyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide; N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide
Clinical Status
Approved
Disease Indication Migraine ICD-11: 8A80 [1]
PubChem CID
4440
Formula
C17H25N3O2S
Canonical SMILES
CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C
InChI
1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3
InChIKey
AMKVXSZCKVJAGH-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=4440"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 335.5 Topological Polar Surface Area 73.6
XlogP 2 Complexity 483
Heavy Atom Count 23 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Naratriptan 2.5 mg tablet 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
Lactose monohydrate; Fd&c blue no. 1; Magnesium stearate; Ferric oxide yellow; Ferrosoferric oxide; Talc; Titanium dioxide; Croscarmellose sodium; Polyethylene glycol 3350; Polyethylene glycol 4000; Polyvinyl alcohol; Aluminum oxide; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h)
                   Dosage Form Oral Tablet
                   Company Teva 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]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [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
Anhydrous lactose; D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Aluminum oxide; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Paddock Laboratories,
                   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) [6]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [6]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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; Fd&c blue no. 2; Indigotindisulfonate sodium; Magnesium stearate; Ferric oxide yellow; Titanium dioxide; Triacetin; Croscarmellose sodium; Hypromellose, unspecified; Microcrystalline cellulose
                   Dosage Form Oral Tablet
                   Company GlaxoSmithKline
                   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) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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
Anhydrous lactose; Lactose monohydrate; Fd&c blue no. 2; Magnesium stearate; Ferric oxide yellow; Titanium dioxide; Triacetin; Croscarmellose sodium; Cellulose, microcrystalline; Hypromellose 2910 (15 mpa.s)
                   Dosage Form Oral Tablet
                   Company Sandoz
                   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) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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
Anhydrous lactose; Fd&c blue no. 2; Magnesium stearate; Ferric oxide yellow; Titanium dioxide; Triacetin; Croscarmellose sodium; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Mylan Pharamceuticals
                   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) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [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
Anhydrous lactose; Fd&c blue no. 2; Magnesium stearate; Ferric oxide yellow; Titanium dioxide; Triacetin; Croscarmellose sodium; Cellulose, microcrystalline; Hypromellose 2910 (6 mpa.s)
                   Dosage Form Oral Tablet
                   Company OrchidPharma
                   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) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [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
Anhydrous lactose; Magnesium stearate; Croscarmellose sodium; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   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) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Anhydrous lactose; Magnesium stearate; Talc; Titanium dioxide; Croscarmellose sodium; Cellulose, microcrystalline; Hypromellose 2910 (6 mpa.s); Polyethylene glycol 8000
                   Dosage Form Oral Tablet
                   Company Heritage Pharmaceuticals
                   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) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
          Naratriptan 1 mg tablet 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
Lactose monohydrate; Fd&c blue no. 1; Magnesium stearate; Ferric oxide yellow; Ferrosoferric oxide; Talc; Titanium dioxide; Croscarmellose sodium; Polyethylene glycol 4000; Polyvinyl alcohol; Aluminum oxide; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Polyethylene glycol 3500
                   Dosage Form Oral Tablet
                   Company Teva 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]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [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
Anhydrous lactose; Fd&c blue no. 2; Magnesium stearate; Ferric oxide yellow; Titanium dioxide; Triacetin; Croscarmellose sodium; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Mylan Pharamceuticals
                   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) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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
Anhydrous lactose; Magnesium stearate; Ferric oxide yellow; Titanium dioxide; Croscarmellose sodium; Polyethylene glycol 400; Cellulose, microcrystalline; Hypromellose 2910 (5 mpa.s)
                   Dosage Form Oral Tablet
                   Company Heritage Pharmaceuticals
                   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) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [5]
             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
Anhydrous lactose; Magnesium stearate; Croscarmellose sodium; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company West-Ward Pharmaceticals
                   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) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Anhydrous lactose; Lactose monohydrate; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Cellulose, microcrystalline; Hypromellose 2910 (15 mpa.s)
                   Dosage Form Oral Tablet
                   Company Sandoz
                   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) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [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
Anhydrous lactose; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Paddock Laboratories,
                   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) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [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
Anhydrous lactose; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Cellulose, microcrystalline; Hypromellose 2910 (6 mpa.s)
                   Dosage Form Oral Tablet
                   Company OrchidPharma
                   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) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
             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, unspecified form; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Hypromellose, unspecified; Microcrystalline cellulose
                   Dosage Form Oral Tablet
                   Company GlaxoSmithKline
                   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) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
References
1 FDA label for approved naratriptan 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 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
6 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.

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