Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00616)
Name
Saxagliptin
Synonyms    Click to Show/Hide the Synonyms of This API
Saxagliptin; Onglyza; 361442-04-8; BMS-477118; BMS 477118; OPC-262; UNII-8I7IO46IVQ; 8I7IO46IVQ; CHEMBL385517; CHEBI:71272; BMS-477118-11; (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile; (1S,3S,5S)-2-((2S)-Amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl)-2-azabicyclo(3.1.0)hexane-3-carbonitrile; (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile; BMS477118; Saxagliptin [INN]; Saxagliptine; Saxagliptin (BMS-477118,Onglyza); HSDB 8199; OPC 262; NCGC00242597-01; Saxagliptin anhydrous; 1073057-20-1; Saxagliptin (USAN/INN); DSSTox_CID_28506; DSSTox_RID_82778; DSSTox_GSID_48580; SCHEMBL17168; 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)-; cc-226; MLS006011223; GTPL6316; Saxagliptin - BMS-477118; DTXSID7048580; SCHEMBL20243458; BDBM11542; HMS3264P11; Pharmakon1600-01502500; Tox21_112908; BDBM50225074; NSC760407; AKOS015896547; AC-6008; CCG-213084; CCG-267647; CS-0650; DB06335; EX-7795; NSC-760407; NCGC00242597-02; HY-10285; SMR004702984; AM20090693; CAS-361442-04-8; D08996; Q-4418; AB01562984_01; AB01562984_02; Q3121121; BRD-A81513827-001-03-6; Z2235802036; (S)-3-Hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt; (1S,6S)-2-(2-adamantan-1-yl-2-amino-acetyl)-2-aza-bicyclo[3.1.0]hexane-3-carbonitrile; (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile; 2,2,2-trifluoroacetic acid; (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-1-oxoethyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile; (1S,3S,5S)-2-[(S)-2-amino-2-(3-hydroxy-adamantan-1-yl)-acetyl]-2-aza-bicyclo[3.1.0]hexane-3-carbonitrile; 2-Azabicyclo(3.1.0)hexane-3-carbonitrile, 2-((2S)-amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl) , (1S,3S,5S)-
Clinical Status
Approved
Disease Indication Diabetes mellitus ICD-11: 5A10 [1]
PubChem CID
11243969
Formula
C18H25N3O2
Canonical SMILES
C1[C@@H]2C[C@@H]2N([C@@H]1C#N)C(=O)[C@H](C34CC5CC(C3)CC(C5)(C4)O)N
InChI
1S/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10?,11?,12-,13+,14+,15-,17?,18?/m1/s1
InChIKey
QGJUIPDUBHWZPV-SGTAVMJGSA-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=11243969"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 315.4 Topological Polar Surface Area 90.4
XlogP 0.7 Complexity 609
Heavy Atom Count 23 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Saxagliptin Hydrochloride eq 2.5mg base 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; Microcrystalline Cellulose; Croscarmellose Sodium; Magnesium Stearate; Polyvinyl Alcohol; Polyethylene Glycol; Titanium Dioxide; Talc; Iron Oxides
                   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]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
          Saxagliptin Hydrochloride eq 5mg base 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; Microcrystalline Cellulose; Croscarmellose Sodium; Magnesium Stearate; Polyvinyl Alcohol; Polyethylene Glycol; Titanium Dioxide; Talc; Iron Oxides
                   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]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
          Saxagliptin 2.5 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; Magnesium stearate; Croscarmellose sodium; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company AstraZeneca; 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]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
          Saxagliptin 5 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; Magnesium stearate; Croscarmellose sodium; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company AstraZeneca; Cardinal Health; E.R. Squibb & Sons; Physicians Total Care
                   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]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
References
1 FDA label for approved saxagliptin 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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