Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00231)
Name
Entacapone
Synonyms    Click to Show/Hide the Synonyms of This API
ENTACAPONE; 130929-57-6; Comtan; Comtess; Entacaponum; OR-611; Entacapona; (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylacrylamide; (E)-alpha-Cyano-N,N-diethyl-3,4-dihydroxy-5-nitrocinnamamide; 2-Cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide; UNII-4975G9NM6T; 116314-67-1; CHEMBL953; (2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide; CHEBI:4798; N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl) acrylamide; 4975G9NM6T; (2E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide; (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide; 2-Propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (2E)-; Entacaponum [INN-Latin]; Entacapona [INN-Spanish]; NCGC00164555-01; Entacom; DSSTox_CID_26439; DSSTox_RID_81615; DSSTox_GSID_46439; cis-Entacapone; OR 611; 2-Propenamide,2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-,(2E)-; (E)-Entacapone; (~{E})-2-cyano-~{N},~{N}-diethyl-3-[3-nitro-4,5-bis(oxidanyl)phenyl]prop-2-enamide; (E)-2-CYANO-3-(5-(DIHYDROXYAMINO)-3,4-DIOXOCYCLOHEXA-1,5-DIENYL)-N,N-DIETHYLACRYLAMIDE; Comtan (TN); CAS-130929-57-6; SR-05000001452; (E)-2-cyano-3-(3,4-dihydroxy-5-nitro-phenyl)-N,N-diethyl-prop-2-enamide; 2-Propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-; COM-998; Entacapone [USAN:USP:INN:BAN]; 1047659-02-8; (E)-2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide; SCHEMBL34504; SCHEMBL34505; BIDD:GT0026; Entacapone (JP17/USP/INN); GTPL6647; DTXSID5046439; SCHEMBL13596593; HSDB 8251; HMS2089O16; HMS3713B20; HMS3885K09; EX-A1130; Tox21_112184; AC-393; BDBM50108879; MFCD00866580; ZINC35342787; AKOS015907685; AKOS015965009; Tox21_112184_1; BCP9000645; CCG-213064; CS-1266; DB00494; NCGC00164555-02; NCGC00164555-03; HY-14280; AB0105766; SW199035-2; C07943; D00781; J90011; K-4072; AB01275450-01; AB01275450_02; AB01275450_03; 929E576; A806167; Q416444; J-005902; J-008069; SR-05000001452-1; SR-05000001452-2; SR-05000001452-3; BRD-K83636919-001-01-4; (E)-N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide; (E)-N, N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide; (E)-2-cyano-N,N-diethyl-3-[3-nitro-4,5-bis(oxidanyl)phenyl]prop-2-enamide; 2-cyano-3-(5-dihydroxyamino-3,4-dioxo-1-cyclohexa-1,5-dienyl)-N,N-diethyl-prop-2-enamide
Clinical Status
Approved
Disease Indication Parkinsonism ICD-11: 8A00 [1]
PubChem CID
5281081
Formula
C14H15N3O5
Canonical SMILES
CCN(CC)C(=O)/C(=C/C1=CC(=C(C(=C1)O)O)[N+](=O)[O-])/C#N
InChI
1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
InChIKey
JRURYQJSLYLRLN-BJMVGYQFSA-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=5281081"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 305.29 Topological Polar Surface Area 130
XlogP 2.1 Complexity 500
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Entacapone 200 mg tablet Click to Show/Hide the Full List of Formulation(s):        12 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
D&c yellow no. 10; Fd&c yellow no. 6; Magnesium stearate; Mannitol; Talc; Titanium dioxide; Triacetin; Croscarmellose sodium; Silicon dioxide; Cellulose, microcrystalline; Hydrogenated cottonseed oil; Hypromellose 2910 (6 mpa.s); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Wockhardt
                   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]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [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
Sucralose; Magnesium stearate; Mannitol; Ferric oxide red; Ferric oxide yellow; Glycerin; Titanium dioxide; Croscarmellose sodium; Polysorbate 80; Cellulose, microcrystalline; Hydrogenated cottonseed oil; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sucralose DIG Info Carbonic anhydrase II (Ki = 300 nM) [6]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [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
Lactose monohydrate; Magnesium stearate; Mannitol; Ferric oxide red; Ferric oxide yellow; Glycerin; Sucrose; Titanium dioxide; Croscarmellose sodium; Polysorbate 80; Cellulose, microcrystalline; Hydrogenated cottonseed oil; Hypromellose 2910 (6 mpa.s); Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Aurobindo Pharma; AvPAK; Avera McKennan Hospital
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [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
Lactose monohydrate; Magnesium stearate; Mannitol; Ferric oxide red; Ferric oxide yellow; Glycerin; Sucrose; Titanium dioxide; Croscarmellose sodium; Polysorbate 80; Hydrogenated cottonseed oil; Hypromellose 2910 (6 mpa.s); Microcrystalline cellulose; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company American Health Packaging
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             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
Magnesium stearate; Mannitol; Ferric oxide red; Ferric oxide yellow; Glycerin; Sucrose; Titanium dioxide; Croscarmellose sodium; Polysorbate 80; Cellulose, microcrystalline; Hydrogenated cottonseed oil; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Aphena Pharma Solutions-Tennessee; Wockhardt
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             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
Magnesium stearate; Mannitol; Ferric oxide red; Ferric oxide yellow; Glycerin; Sucrose; Titanium dioxide; Croscarmellose sodium; Polysorbate 80; Cellulose, microcrystalline; Hydrogenated cottonseed oil; Hypromelloses
                   Dosage Form Oral Tablet
                   Company AvKARE; Avera McKennan Hospital; Mylan Pharamceuticals; Sun Pharmaceutical Industries
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             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
Magnesium stearate; Mannitol; Ferric oxide red; Ferric oxide yellow; Glycerin; Sucrose; Titanium dioxide; Croscarmellose sodium; Polysorbate 80; Cellulose, microcrystalline; Hydroxypropyl cellulose
                   Dosage Form Oral Tablet
                   Company Cardinal Health
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             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
Magnesium stearate; Mannitol; Ferric oxide red; Ferric oxide yellow; Glycerin; Sucrose; Titanium dioxide; Croscarmellose sodium; Polysorbate 80; Hydrogenated cottonseed oil; Hypromellose, unspecified; Microcrystalline cellulose
                   Dosage Form Oral Tablet
                   Company Novartis Pharmaceuticals Corporation
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             Drug Formulation 9 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; Mannitol; Ferric oxide red; Ferric oxide yellow; Glycerin; Sucrose; Titanium dioxide; Croscarmellose sodium; Polysorbate 80; Cellulose, microcrystalline; Hydrogenated cottonseed oil; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Kaiser Foundation Hospitals; Sandoz
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             Drug Formulation 10 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; Mannitol; Ferric oxide red; Ferric oxide yellow; Glycerin; Titanium dioxide; Croscarmellose sodium; Polysorbate 80; Cellulose, microcrystalline; Hypromellose 2910 (5 mpa.s)
                   Dosage Form Oral Tablet
                   Company Sun Pharmaceutical Industries
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             Drug Formulation 11 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; Ferric oxide red; Ferric oxide yellow; Propylene glycol; Talc; Titanium dioxide; Croscarmellose sodium; Povidone; Cellulose, microcrystalline; Hypromelloses; Starch, corn
                   Dosage Form Oral Tablet
                   Company Macleods Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [7]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [8]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             Drug Formulation 12 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; Ferric oxide red; Ferric oxide yellow; Titanium dioxide; Water; Polyoxyl 40 hydrogenated castor oil; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Ajanta Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrogenated polyoxyl 40 castor oil DIG Info Cytochrome P450 2C9 (IC50 = 30 uM) [9]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved entacapone 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 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
4 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
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 Sweet Binders: Carbonic Anhydrase IX in Complex with Sucralose. ACS Med Chem Lett. 2018 May 10; 9(7):657-661.
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 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
9 Effects of non-ionic surfactants on cytochrome P450-mediated metabolism in vitro. Eur J Pharm Biopharm. 2011 May;78(1):166-72.

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