Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00232)
Name
Entecavir
Synonyms    Click to Show/Hide the Synonyms of This API
142217-69-4; Baraclude; Entecavir anhydrous; BMS 200475; UNII-NNU2O4609D; BMS-200475; 209216-23-9; entecavir (anhydrous); CHEBI:473990; SQ 34676; SQ-34676; BMS-200475-01; Entecavir [USAN:INN]; NNU2O4609D; 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one; MFCD00907887; 142217-69-4 (free); 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one; anhydrous entecavir; 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-; 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-; 2-AMINO-9-((1S,3R,4S)-4-HYDROXY-3-(HYDROXYMETHYL)-2-METHYLENECYCLOPENTYL)-1H-PURIN-6(9H)-ONE; SQ 34,676; HSDB 7334; Entecavir (INN); NCGC00164563-01; 1333204-94-6; SQ34676; CHEMBL713; DSSTox_CID_26446; DSSTox_RID_81621; DSSTox_GSID_46446; SCHEMBL28648; DTXSID4046446; Entecavir, >=98% (HPLC); SCHEMBL15198001; 188399-46-4; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one; ZINC3802690; Tox21_112192; ABP001043; BDBM50248008; AKOS015854916; AKOS015920226; AKOS025312554; AC-1593; CCG-267218; CS-3160; DB00442; GS-6386; LS41110; PB30663; 2-amino-9-[4-hydroxy-3-(hydroxymethyl)-2-methylidene-cyclopentyl]-3H-purin-6-one; NCGC00164563-04; NCGC00164563-09; NCGC00164563-13; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one; BR-77289; HY-13623; AB0071164; AM20080880; CAS-142217-69-4; D07896; J90027; S-7388; 217E694; AR-270/43507901; Q418586; methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one; BRD-K08206212-001-01-2; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-; 9-[(1S,3R,4S)-4-Hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]guanine; 2-amino-9-[4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one; 2-amino-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-1,9-dihydro-6H-purin-6-one; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylene-cyclopentyl]-1H-purin-6-one; 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one hydrate (1:1); 2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl]-3,9-dihydro-purin-6-one; 2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one; 6-H-Purin-6-one-,2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]
Clinical Status
Approved
Disease Indication Viral hepatitis ICD-11: 1E51 [1]
PubChem CID
135398508
Formula
C12H15N5O3
Canonical SMILES
C=C1[C@H](C[C@@H]([C@H]1CO)O)N2C=NC3=C2N=C(NC3=O)N
InChI
1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1
InChIKey
QDGZDCVAUDNJFG-FXQIFTODSA-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=135398508"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 277.28 Topological Polar Surface Area 126
XlogP -1.3 Complexity 480
Heavy Atom Count 20 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Entecavir 1 mg tablet Click to Show/Hide the Full List of Formulation(s):        10 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
Fd&c red no. 40; Fd&c blue no. 2; Magnesium stearate; Mannitol; Ferric oxide yellow; Talc; Titanium dioxide; Polyethylene glycol 3350; Polyethylene glycol 4000; Crospovidone, unspecified; Microcrystalline cellulose; Polyvinyl alcohol, unspecified; Starch, corn
                   Dosage Form Oral Tablet
                   Company Teva Pharmaceuticals
                   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. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 3350 DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [6]
             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
Calcium carbonate; Sodium stearyl fumarate; Citric acid monohydrate; Ferric oxide red; Titanium dioxide; Carboxymethylcellulose sodium; Hypromelloses; Starch, corn; Thiamine mononitrate
                   Dosage Form Oral Tablet
                   Company Camber Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Calcium carbonate DIG Info Carbonic anhydrase IX (Ki = 8600 nM) [7]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [8]
Carboxymethylcellulose sodium DIG Info Albendazole monooxygenase (EC50 = 12.6 uM) [9]
             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; Fd&c yellow no. 6; Magnesium stearate; Ferric oxide yellow; Talc; Titanium dioxide; Crospovidone (12 mpa.s at 5%); Crospovidone, unspecified; Microcrystalline cellulose; Peg-2 stearate; Polyvinyl alcohol (100000 mw)
                   Dosage Form Oral Tablet
                   Company Par Pharmaceutical
                   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) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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; Ferric oxide red; Titanium dioxide; Crospovidone; Polyethylene glycol 400; Cellulose, microcrystalline; Hypromelloses; Povidones
                   Dosage Form Oral Tablet
                   Company Par Pharmaceutical
                   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) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [6]
             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
Lactose monohydrate; Magnesium stearate; Ferric oxide red; Ferric oxide yellow; Talc; Titanium dioxide; Crospovidone; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Cadila Healthcare; Zydus 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) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Magnesium stearate; Ferric oxide red; Titanium dioxide; Povidone; Cellulose, microcrystalline; Crospovidone (12 mpa.s at 5%); Hypromelloses; Polyethylene glycol 8000
                   Dosage Form Oral Tablet
                   Company Amneal Pharmaceuticals; Marlex Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [9]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Magnesium stearate; Ferric oxide red; Titanium dioxide; Polyethylene glycol 400; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hypromellose 2910 (6 mpa.s); Povidones
                   Dosage Form Oral Tablet
                   Company Cipla; NorthStar Rx
                   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) [5]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [6]
             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 monohydrate; Magnesium stearate; Ferric oxide red; Titanium dioxide; Polyethylene glycol 400; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hypromelloses; Povidones
                   Dosage Form Oral Tablet
                   Company E.R. Squibb & Sons
                   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) [5]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [6]
             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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Crospovidone; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Aurobindo Pharma; Lucid Pharma
                   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) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Magnesium stearate; Ferric oxide red; Titanium dioxide; Cellulose, microcrystalline; Crospovidone (12 mpa.s at 5%); Hypromelloses; Polyethylene glycol 8000; Povidones
                   Dosage Form Oral Tablet
                   Company AvKARE
                   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) [5]
          Entecavir 0.5 mg tablet Click to Show/Hide the Full List of Formulation(s):        11 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
Calcium carbonate; Sodium stearyl fumarate; Citric acid monohydrate; Titanium dioxide; Carboxymethylcellulose sodium; Polysorbate 80; Polyethylene glycols; Starch, corn; Thiamine mononitrate
                   Dosage Form Oral Tablet
                   Company Camber Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Calcium carbonate DIG Info Carbonic anhydrase IX (Ki = 8600 nM) [7]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [8]
Carboxymethylcellulose sodium DIG Info Albendazole monooxygenase (EC50 = 12.6 uM) [9]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [2]
             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
Magnesium stearate; Mannitol; Talc; Titanium dioxide; Polyethylene glycol 3350; Crospovidone, unspecified; Microcrystalline cellulose; Polyvinyl alcohol, unspecified; Starch, corn
                   Dosage Form Oral Tablet
                   Company Teva Pharmaceuticals
                   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]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 3350 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; Titanium dioxide; Crospovidone; Polyethylene glycol 400; Polysorbate 80; Cellulose, microcrystalline; Hypromelloses; Povidones
                   Dosage Form Oral Tablet
                   Company Par Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [6]
             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; Titanium dioxide; Polyethylene glycol 400; Polysorbate 80; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hypromelloses; Povidones
                   Dosage Form Oral Tablet
                   Company E.R. Squibb & Sons
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [6]
             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
Lactose monohydrate; Magnesium stearate; Talc; Titanium dioxide; Crospovidone; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Cadila Healthcare; Zydus 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) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Crospovidone; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Aurobindo Pharma; Lucid Pharma
                   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) [5]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Povidone; Cellulose, microcrystalline; Crospovidone (12 mpa.s at 5%); Hypromelloses; Polyethylene glycol 8000
                   Dosage Form Oral Tablet
                   Company Amneal Pharmaceuticals; Marlex Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [9]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Polyethylene glycol 6000; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Hypromellose 2910 (15 mpa.s); Povidones
                   Dosage Form Oral Tablet
                   Company Cipla; NorthStar Rx
                   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) [5]
Polyethylene glycol 6000 DIG Info Albendazole monooxygenase (Inhibition ratio < 70 %) [6]
             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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Polysorbate 80; Crospovidone (12 mpa.s at 5%); Hypromellose, unspecified; Microcrystalline cellulose; Peg-2 stearate; Povidone, unspecified
                   Dosage Form Oral Tablet
                   Company Par Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Crospovidone (15 mpa.s at 5%); Hypromellose, unspecified; Microcrystalline cellulose; Polyethylene glycol, unspecified
                   Dosage Form Oral Tablet
                   Company American Health Packaging
                   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) [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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Cellulose, microcrystalline; Crospovidone (12 mpa.s at 5%); Hypromelloses; Polyethylene glycol 8000; Povidones
                   Dosage Form Oral Tablet
                   Company AvKARE
                   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) [5]
References
1 FDA label for approved entecavir 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 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
4 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.
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 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
7 Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, IV, V, and IX with anions isosteric and isoelectronic with sulfate, nitrate, and carbonate. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):567-71.
8 Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents. Eur J Med Chem. 2014 Apr 9; 76:291-300.
9 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.