Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00686)
Name
Tolcapone
Synonyms    Click to Show/Hide the Synonyms of This API
Tolcapone; 134308-13-7; Tasmar; Ro 40-7592; (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone; 3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone; (3,4-dihydroxy-5-nitrophenyl)(p-tolyl)methanone; Ro-40-7592; (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone; UNII-CIF6334OLY; Methanone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-; MFCD00866569; CHEMBL1324; CIF6334OLY; CHEBI:63630; Ro-407592; NCGC00181767-01; 3,4-dihydroxy-5-nitro-4'-methylbenzophenone; 4'-methyl-3,4-dihydroxy-5-nitrobenzophenone; DSSTox_CID_3685; DSSTox_RID_77146; DSSTox_GSID_23685; Talcapone; Tasmar (TN); CCRIS 7904; CAS-134308-13-7; 1246816-93-2; Tolcapone [USAN:USP:INN:BAN]; Tolcapone (JAN/USP/INN); SCHEMBL33869; MLS006012044; BIDD:GT0032; GTPL6646; DTXSID3023685; Tolcapone, >=98% (HPLC); HMS2089K14; HMS3652M17; HMS3715D16; HMS3872F03; HMS3885G18; BCP09156; EBD47899; Tox21_112963; Tox21_302414; 3,4-dihydroxy-4 inverted exclamation mark -methyl-5-nitrobenzophenone; AC-791; BDBM50108877; ZINC35342789; AKOS015902328; Tox21_112963_1; AS-7085; CCG-221217; CS-1173; DB00323; KS-1314; NCGC00181767-02; NCGC00181767-03; NCGC00255188-01; AK671145; HY-17406; SMR001614567; SY102278; AB0012754; DB-013561; FT-0631149; SW219511-1; C07949; D00786; W-5146; AB01275441-01; AB01275441_02; (3,4-Dihydroxy-5-nitro-phenyl)-p-tolyl-methanone; 308T137; Q413840; SR-05000001444; Q-201840; SR-05000001444-1; BRD-K10852020-001-01-1; 5-[(4-METHYLPHENYL)CARBONYL]-3-NITROBENZENE-1,2-DIOL; Tolcapone, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Parkinsonism ICD-11: 8A00 [1]
PubChem CID
4659569
Formula
C14H11NO5
Canonical SMILES
CC1=CC=C(C=C1)C(=O)C2=CC(=C(C(=C2)O)O)[N+](=O)[O-]
InChI
1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3
InChIKey
MIQPIUSUKVNLNT-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=4659569"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 273.24 Topological Polar Surface Area 103
XlogP 3.3 Complexity 372
Heavy Atom Count 20 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Tolcapone 100 mg tablet 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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Anhydrous dibasic calcium phosphate; Ferric oxide red; Ferric oxide yellow; Talc; Titanium dioxide; Triacetin; Povidone k30; Ethylcellulose, unspecified; Microcrystalline cellulose; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Valeant Pharmaceuticals
                   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) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             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 monohydrate; Sodium lauryl sulfate; Magnesium stearate; Anhydrous dibasic calcium phosphate; Ferric oxide red; Ferric oxide yellow; Talc; Titanium dioxide; Triacetin; Ethylcellulose, unspecified; Hypromellose, unspecified; Microcrystalline cellulose; Povidone, unspecified; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Oceanside Pharmaceuticals
                   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) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             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; Ferric oxide red; Ferric oxide yellow; Talc; Titanium dioxide; Polyvinyl alcohol; Povidone k30; Calcium phosphate, dibasic, anhydrous; Cellulose, microcrystalline; Polyethylene glycols; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Par Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Tolcapone 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
Lactose monohydrate; Sodium lauryl sulfate; Magnesium stearate; Anhydrous dibasic calcium phosphate; Ferric oxide red; Talc; Titanium dioxide; Triacetin; Povidone k30; Cellulose, microcrystalline; Ethylcelluloses; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Valeant Pharmaceuticals
                   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) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Calcium hydrogenphosphate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved tolcapone 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 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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