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
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=10324367"></iframe>
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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