Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00167)
Name
Dapagliflozin
Synonyms    Click to Show/Hide the Synonyms of This API
Dapagliflozin; 461432-26-8; BMS-512148; Forxiga; Farxiga; BMS 512148; (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; UNII-1ULL0QJ8UC; (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol; 1ULL0QJ8UC; CHEMBL429910; CHEBI:85078; Dapagliflozin [USAN:INN]; BMS512148; (2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; Forxiga (TN); CHEMBL3125458; (1S)-1,5-anhydro-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-D-glucitol; D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-, (1S)-; (2S,3R,4R,5S,6R)-2-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-6-(hydroxymethyl)oxane-3,4,5-triol; (1S)-1,5-anhydro-1-C-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-D-glucitol; D-Glucitol, 1,5-anhydro-1-C-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-, (1S)-; (2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol; C-aryl glucoside, 6; PubChem22435; Tube101; 960404-48-2; Dapagliflozin (USAN/INN); 2-(3-(4-Ethoxybenzyl)-4-chlorophenyl)-6-hydroxymethyltetrahydro-2H-pyran-3,4,5-triol; cc-205; SCHEMBL157820; GLU006; GTPL4594; BDBM20880; DTXSID20905104; EX-A005; BCPP000265; AOB87300; ZINC3819138; BDBM50448923; CD0219; MFCD13182359; AKOS005145763; BCP9000583; BL-0052; BMS5121458; CCG-229917; CS-0781; DB06292; EX-7214; PB11055; NCGC00250402-09; AC-24699; HY-10450; A25150; C22193; D08897; Q-3845; 432D268; Q409898; J-500392; BRD-K58160573-001-01-3; BRD-K58160573-001-05-4; 1-[3-(beta-D-Glucopyranosyl)-6-chlorobenzyl]-4-ethoxybenzene; (2S, 3R, 4R, 5S, 6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol; (2S,3R,4R,5S,6R)-2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol; (2S,3R,4R,5S,6R)-2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;BMS-512148; (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
Clinical Status
Approved
Disease Indication Diabetes mellitus ICD-11: 5A10 [1]
PubChem CID
9887712
Formula
C21H25ClO6
Canonical SMILES
CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)Cl
InChI
1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1
InChIKey
JVHXJTBJCFBINQ-ADAARDCZSA-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=9887712"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 408.9 Topological Polar Surface Area 99.4
XlogP 2.3 Complexity 472
Heavy Atom Count 28 Rotatable Bond Count 6
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Dapagliflozin Propanediol 5mg 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
Microcrystalline Cellulose; Anhydrous Lactose; Crospovidone; Silicon Dioxide; Magnesium Stearate; Polyvinyl Alcohol; Titanium Dioxide; Polyethylene Glycol; Talc; Yellow Iron Oxide
                   Dosage Form Tablet
                   Company Astrazeneca Ab
                   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) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Dapagliflozin Propanediol 10mg 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
Microcrystalline Cellulose; Anhydrous Lactose; Crospovidone; Silicon Dioxide; Magnesium Stearate; Polyvinyl Alcohol; Titanium Dioxide; Polyethylene Glycol; Talc; Yellow Iron Oxide
                   Dosage Form Tablet
                   Company Astrazeneca Ab
                   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) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Dapagliflozin 10 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 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
Anhydrous lactose; Magnesium stearate; Crospovidone; Silicon dioxide; Cellulose, microcrystalline
                   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) [3]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide 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
Anhydrous lactose; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%)
                   Dosage Form Oral Tablet
                   Company AstraZeneca
                   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) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Dapagliflozin 5 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 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
Anhydrous lactose; Magnesium stearate; Crospovidone; Silicon dioxide; Cellulose, microcrystalline
                   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) [3]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Silicon dioxide 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
Anhydrous lactose; Magnesium stearate; Silicon dioxide; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%)
                   Dosage Form Oral Tablet
                   Company AstraZeneca
                   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) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved dapagliflozin from the official website of the U.S. Food and Drug Administration.
2 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
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 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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