Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00073)
Name
Boceprevir
Synonyms    Click to Show/Hide the Synonyms of This API
Boceprevir; Victrelis; 394730-60-0; SCH 503034; EBP 520; UNII-89BT58KELH; SCH503034; SCH-503034; 89BT58KELH; CHEBI:68621; EBP-520; (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide; (1R,2S,5S)-N-(4-AMINO-1-CYCLOBUTYL-3,4-DIOXOBUTAN-2-YL)-3-[(2S)-2-(TERT-BUTYLCARBAMOYLAMINO)-3,3-DIMETHYLBUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXAMIDE; (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[N-(tert-butylcarbamoyl)-3-methyl-L-valyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide; (1S,4S,5R)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxo-propyl]-3-[(2S)-2-(tert-butylcarbamoylamino)-3,3-dimethyl-butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-4-carboxamide; 3-{[(1R,2S,5S)-3-[(2S)-2-[(tert-butylcarbamoyl)amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2-yl]formamido}-4-cyclobutyl-2-oxobutanamide; Boceprevir [USAN:INN]; HSDB 8081; Victrelis(TM); Victrelis (TN); Boceprevir & NM107; Boceprevir (INN/USAN); SCHEMBL640836; CHEMBL218394; EBP520; GTPL7876; BDBM12311; DTXSID30960103; BCP02502; EX-A1336; MFCD22208555; AKOS005145787; EBP-520;SCH503034; CCG-269852; CS-0361; DB08873; DT-0021; NCGC00378631-01; HY-10237; SCH 503034 & NM107; D08876; Q410551; J-519910; (1R,2S,5S)-N-(3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-((2S)-2-(((1,1-dimethylethyl)carbamoyl)amino)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo(3.1.0)hexane-2-carboxamide; (1r,5s)-n-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[2(s)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2(s)-carboxamide; 3-Azabicyclo(3.1.0)hexane-2-carboxamide, N-(3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl)-3-((2S)-2-((((1,1- dimethylethyl)amino)carbonyl)amino)-3,3-dimethyl-1-oxobutyl)-6,6- dimethyl-, (1R,2S,5S)-; 3-azabicyclo[3.1.0]hexane-2-carboxamide, N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-, (1R,2S,5S)-; 3-Azabicyclo[3.1.0]hexane-2-carboxamide,N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-,(1R,2S,5S)-; N-(4-Amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-{N-[(tert-butylamino)(hydroxy)methylidene]-3-methylvalyl}-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboximidic acid
Clinical Status
Approved
Disease Indication Viral hepatitis ICD-11: 1E51 [1]
PubChem CID
10324367
Formula
C27H45N5O5
Canonical SMILES
CC1([C@@H]2[C@H]1[C@H](N(C2)C(=O)[C@H](C(C)(C)C)NC(=O)NC(C)(C)C)C(=O)NC(CC3CCC3)C(=O)C(=O)N)C
InChI
1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1
InChIKey
LHHCSNFAOIFYRV-DOVBMPENSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 519.7 Topological Polar Surface Area 151
XlogP 3.1 Complexity 959
Heavy Atom Count 37 Rotatable Bond Count 10
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Boceprevir 200 mg 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
Lactose monohydrate; Sodium lauryl sulfate; D&c yellow no. 10; Fd&c red no. 40; Butyl alcohol; Fd&c blue no. 1; Fd&c yellow no. 6; Isopropyl alcohol; Magnesium stearate; Ammonia; Ferric oxide red; Propylene glycol; Titanium dioxide; Croscarmellose sodium; Alcohol; Aluminum oxide; Gelatin, unspecified; Microcrystalline cellulose; Povidone, unspecified; Shellac
                   Dosage Form Oral Capsule
                   Company Merck Sharp & Dohme
                   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]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
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]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [6]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [6]
References
1 FDA label for approved boceprevir 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 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
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 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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