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Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:52 UTC |
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Update Date | 2022-03-07 02:52:03 UTC |
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HMDB ID | HMDB0015634 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Saxagliptin |
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Description | Saxagliptin (rINN), previously identified as BMS-477118, is a new oral hypoglycemic (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. It was developed by Bristol-Myers Squibb. A New Drug Application for saxagliptin in the treatment of type 2 diabetes was submitted to the FDA in June 2008. It was based on a drug development program with 8 randomized trials: 1 phase 2 dose-ranging (2.5 - 100 mg/d) study; 6 phase 3, 24-week controlled trials with additional controlled follow-up from 12 to 42 months, double-blinded throughout; and one 12-week mechanism-of-action trial with a 2-year follow-up period. In June 2008, it was announced that Onglyza would be the trade name under which saxagliptin will be marketed. |
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Structure | N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2 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 |
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Synonyms | Value | Source |
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(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 | ChEBI | BMS 477118 | ChEBI | BMS-477118 | ChEBI | Onglyza | HMDB | 3-Hydroxyadamantylglycine-4,5-methanoprolinenitrile hydrate | HMDB |
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Chemical Formula | C18H25N3O2 |
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Average Molecular Weight | 315.41 |
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Monoisotopic Molecular Weight | 315.194677059 |
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IUPAC Name | (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile |
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Traditional Name | saxagliptin |
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CAS Registry Number | 361442-04-8 |
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SMILES | N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2 |
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InChI Identifier | 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 |
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InChI Key | QGJUIPDUBHWZPV-SGTAVMJGSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alpha amino acid amides |
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Alternative Parents | |
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Substituents | - Alpha-amino acid amide
- N-acyl-piperidine
- N-acylpyrrolidine
- Piperidine
- Cyclic alcohol
- Pyrrolidine
- Tertiary carboxylic acid amide
- Tertiary alcohol
- Carboxamide group
- Carbonitrile
- Nitrile
- Azacycle
- Organoheterocyclic compound
- Organonitrogen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Primary aliphatic amine
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Organic nitrogen compound
- Primary amine
- Amine
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Saxagliptin,1TMS,isomer #1 | C[Si](C)(C)OC12CC3CC(C1)CC([C@H](N)C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)(C3)C2 | 2593.1 | Semi standard non polar | 33892256 | Saxagliptin,1TMS,isomer #2 | C[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2 | 2678.3 | Semi standard non polar | 33892256 | Saxagliptin,2TMS,isomer #1 | C[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C)(C3)C1)C2 | 2589.8 | Semi standard non polar | 33892256 | Saxagliptin,2TMS,isomer #1 | C[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C)(C3)C1)C2 | 2749.1 | Standard non polar | 33892256 | Saxagliptin,2TMS,isomer #1 | C[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C)(C3)C1)C2 | 3801.1 | Standard polar | 33892256 | Saxagliptin,2TMS,isomer #2 | C[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C | 2808.3 | Semi standard non polar | 33892256 | Saxagliptin,2TMS,isomer #2 | C[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C | 2939.4 | Standard non polar | 33892256 | Saxagliptin,2TMS,isomer #2 | C[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C | 3827.8 | Standard polar | 33892256 | Saxagliptin,3TMS,isomer #1 | C[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2 | 2740.2 | Semi standard non polar | 33892256 | Saxagliptin,3TMS,isomer #1 | C[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2 | 2843.1 | Standard non polar | 33892256 | Saxagliptin,3TMS,isomer #1 | C[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2 | 3644.5 | Standard polar | 33892256 | Saxagliptin,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC([C@H](N)C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)(C3)C2 | 2827.7 | Semi standard non polar | 33892256 | Saxagliptin,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2 | 2910.4 | Semi standard non polar | 33892256 | Saxagliptin,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2 | 3053.3 | Semi standard non polar | 33892256 | Saxagliptin,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2 | 3182.0 | Standard non polar | 33892256 | Saxagliptin,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2 | 3884.2 | Standard polar | 33892256 | Saxagliptin,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C(C)(C)C | 3244.8 | Semi standard non polar | 33892256 | Saxagliptin,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C(C)(C)C | 3369.6 | Standard non polar | 33892256 | Saxagliptin,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C(C)(C)C | 3933.2 | Standard polar | 33892256 | Saxagliptin,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2 | 3423.6 | Semi standard non polar | 33892256 | Saxagliptin,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2 | 3405.0 | Standard non polar | 33892256 | Saxagliptin,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2 | 3754.0 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Saxagliptin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ue9-9810000000-9ea6dee5e5df7feeccf4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Saxagliptin GC-MS (1 TMS) - 70eV, Positive | splash10-0w2i-9640000000-edbf7dd75a87c2e60523 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Saxagliptin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Saxagliptin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 10V, Positive-QTOF | splash10-00kb-0595000000-b2310ee91b2c4452305f | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 20V, Positive-QTOF | splash10-03e9-1920000000-c732c7118b29d97a0034 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 40V, Positive-QTOF | splash10-03di-2900000000-e667b1c85a4362bf4439 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 10V, Negative-QTOF | splash10-03di-0029000000-d07ae8c4becc497aefbf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 20V, Negative-QTOF | splash10-0bta-1954000000-e69611219b56c95d4fcc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 40V, Negative-QTOF | splash10-0a4l-8900000000-c3f60d50781702a5ee87 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 10V, Positive-QTOF | splash10-014i-0319000000-80878b9b214b58a1e91b | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 20V, Positive-QTOF | splash10-001l-1911000000-f644cfc5788567bebc0d | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 40V, Positive-QTOF | splash10-01q9-2900000000-6de6bc70428ab68d2960 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 10V, Negative-QTOF | splash10-03di-0009000000-08c714e7a3cf3391b9ca | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 20V, Negative-QTOF | splash10-08fr-1937000000-046e1094e71a80b7a9b3 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Saxagliptin 40V, Negative-QTOF | splash10-0bt9-4933000000-87784043f4db6b4397a2 | 2021-10-11 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB06335 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB06335 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB06335 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 9419005 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Saxagliptin |
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METLIN ID | Not Available |
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PubChem Compound | 11243969 |
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PDB ID | Not Available |
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ChEBI ID | 71272 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Barnett A: DPP-4 inhibitors and their potential role in the management of type 2 diabetes. Int J Clin Pract. 2006 Nov;60(11):1454-70. [PubMed:17073841 ]
- Crepaldi G, Carruba M, Comaschi M, Del Prato S, Frajese G, Paolisso G: Dipeptidyl peptidase 4 (DPP-4) inhibitors and their role in Type 2 diabetes management. J Endocrinol Invest. 2007 Jul-Aug;30(7):610-4. [PubMed:17848846 ]
- Metzler WJ, Yanchunas J, Weigelt C, Kish K, Klei HE, Xie D, Zhang Y, Corbett M, Tamura JK, He B, Hamann LG, Kirby MS, Marcinkeviciene J: Involvement of DPP-IV catalytic residues in enzyme-saxagliptin complex formation. Protein Sci. 2008 Feb;17(2):240-50. doi: 10.1110/ps.073253208. [PubMed:18227430 ]
- Rosenstock J, Sankoh S, List JF: Glucose-lowering activity of the dipeptidyl peptidase-4 inhibitor saxagliptin in drug-naive patients with type 2 diabetes. Diabetes Obes Metab. 2008 May;10(5):376-86. doi: 10.1111/j.1463-1326.2008.00876.x. Epub 2008 Mar 18. [PubMed:18355324 ]
- Golightly LK, Drayna CC, McDermott MT: Comparative clinical pharmacokinetics of dipeptidyl peptidase-4 inhibitors. Clin Pharmacokinet. 2012 Aug 1;51(8):501-14. doi: 10.2165/11632930-000000000-00000. [PubMed:22686547 ]
- Ali S, Fonseca V: Saxagliptin overview: special focus on safety and adverse effects. Expert Opin Drug Saf. 2013 Jan;12(1):103-9. doi: 10.1517/14740338.2013.741584. Epub 2012 Nov 9. [PubMed:23137182 ]
- Russell S: Incretin-based therapies for type 2 diabetes mellitus: a review of direct comparisons of efficacy, safety and patient satisfaction. Int J Clin Pharm. 2013 Apr;35(2):159-72. doi: 10.1007/s11096-012-9729-9. Epub 2012 Dec 22. [PubMed:23263796 ]
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