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 02:51:58 UTC |
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HMDB ID | HMDB0015394 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Telbivudine |
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Description | Telbivudine is only found in individuals that have used or taken this drug. It is a synthetic thymidine nucleoside analog with specific activity against the hepatitis B virus. Telbivudine is orally administered, with good tolerance, lack of toxicity and no dose-limiting side effects.Telbivudine 5'–triphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate, thymidine 5'–triphosphate. This leads to the chain termination of DNA synthesis, thereby inhibiting viral replication. Incorporation of telbivudine 5'–triphosphate into viral DNA also causes DNA chain termination, resulting in inhibition of HBV replication. Telbivudine inhibits anticompliment or second-strand DNA. |
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Structure | CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)NC1=O InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m1/s1 |
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Synonyms | Value | Source |
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1-(2-Deoxy-beta-L-ribofuranosyl)-5-methyluracil | ChEBI | 2'-Deoxy-L-thymidine | ChEBI | beta-L-2'-Deoxythymidine | ChEBI | Beta-L-Thymidine | ChEBI | Epavudine | ChEBI | L-Deoxythymidine | ChEBI | L-DT | ChEBI | L-Thymidine | ChEBI | LDT | ChEBI | Tyzeka | Kegg | ABBR LDT | Kegg | 1-(2-Deoxy-b-L-ribofuranosyl)-5-methyluracil | Generator | 1-(2-Deoxy-β-L-ribofuranosyl)-5-methyluracil | Generator | b-L-2'-Deoxythymidine | Generator | Β-L-2'-deoxythymidine | Generator | b-L-Thymidine | Generator | Β-L-thymidine | Generator | Telbivudin | HMDB | 1-(2-Deoxy-beta-L-erythropentafuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione | HMDB | beta L 2' Deoxythymidine | HMDB |
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Chemical Formula | C10H14N2O5 |
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Average Molecular Weight | 242.2286 |
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Monoisotopic Molecular Weight | 242.090271568 |
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IUPAC Name | 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione |
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Traditional Name | telbivudine |
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CAS Registry Number | 3424-98-4 |
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SMILES | CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)NC1=O |
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InChI Identifier | InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m1/s1 |
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InChI Key | IQFYYKKMVGJFEH-CSMHCCOUSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleosides |
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Sub Class | Pyrimidine 2'-deoxyribonucleosides |
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Direct Parent | Pyrimidine 2'-deoxyribonucleosides |
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Alternative Parents | |
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Substituents | - Pyrimidine 2'-deoxyribonucleoside
- Pyrimidone
- Hydropyrimidine
- Pyrimidine
- Heteroaromatic compound
- Tetrahydrofuran
- Vinylogous amide
- Lactam
- Secondary alcohol
- Urea
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Alcohol
- Organic nitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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 | 66.8 g/L | Not Available | LogP | -1.4 | 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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Telbivudine,1TMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO)O2)C(=O)[NH]C1=O | 2332.5 | Semi standard non polar | 33892256 | Telbivudine,1TMS,isomer #2 | CC1=CN([C@@H]2C[C@@H](O)[C@H](CO[Si](C)(C)C)O2)C(=O)[NH]C1=O | 2281.7 | Semi standard non polar | 33892256 | Telbivudine,1TMS,isomer #3 | CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)N([Si](C)(C)C)C1=O | 2342.1 | Semi standard non polar | 33892256 | Telbivudine,2TMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O2)C(=O)[NH]C1=O | 2312.0 | Semi standard non polar | 33892256 | Telbivudine,2TMS,isomer #2 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO)O2)C(=O)N([Si](C)(C)C)C1=O | 2397.2 | Semi standard non polar | 33892256 | Telbivudine,2TMS,isomer #3 | CC1=CN([C@@H]2C[C@@H](O)[C@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O | 2384.3 | Semi standard non polar | 33892256 | Telbivudine,3TMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O | 2403.0 | Semi standard non polar | 33892256 | Telbivudine,3TMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O | 2498.5 | Standard non polar | 33892256 | Telbivudine,3TMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O2)C(=O)N([Si](C)(C)C)C1=O | 2732.2 | Standard polar | 33892256 | Telbivudine,1TBDMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O2)C(=O)[NH]C1=O | 2576.3 | Semi standard non polar | 33892256 | Telbivudine,1TBDMS,isomer #2 | CC1=CN([C@@H]2C[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O | 2550.0 | Semi standard non polar | 33892256 | Telbivudine,1TBDMS,isomer #3 | CC1=CN([C@@H]2C[C@@H](O)[C@H](CO)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2574.8 | Semi standard non polar | 33892256 | Telbivudine,2TBDMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]C1=O | 2796.1 | Semi standard non polar | 33892256 | Telbivudine,2TBDMS,isomer #2 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2843.8 | Semi standard non polar | 33892256 | Telbivudine,2TBDMS,isomer #3 | CC1=CN([C@@H]2C[C@@H](O)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2815.4 | Semi standard non polar | 33892256 | Telbivudine,3TBDMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O | 3049.2 | Semi standard non polar | 33892256 | Telbivudine,3TBDMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O | 3118.0 | Standard non polar | 33892256 | Telbivudine,3TBDMS,isomer #1 | CC1=CN([C@@H]2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N([Si](C)(C)C(C)(C)C)C1=O | 2994.0 | 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 - Telbivudine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9420000000-ebaddd47fbf973a127a1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Telbivudine GC-MS (2 TMS) - 70eV, Positive | splash10-00dl-9522000000-ce76edd6f16ba8e724c0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Telbivudine 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 - Telbivudine 10V, Positive-QTOF | splash10-004i-0900000000-9ad72ff6cb2e2dfab911 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 20V, Positive-QTOF | splash10-004i-4900000000-3b1e6c50c2450e123648 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 40V, Positive-QTOF | splash10-004i-6900000000-d30b05dfe1b6d25ebd2b | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 10V, Negative-QTOF | splash10-052g-1940000000-ce16baa1ceb8a83565c2 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 20V, Negative-QTOF | splash10-0ufr-3920000000-c6ff3f238b6fed007635 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 40V, Negative-QTOF | splash10-0006-9200000000-104a4f5a4fe8a0ed5ca3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 10V, Positive-QTOF | splash10-004i-1900000000-ed2addc3268721b7d4d4 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 20V, Positive-QTOF | splash10-004i-8900000000-447c3a769f2fc4753e53 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 40V, Positive-QTOF | splash10-056r-7900000000-ef6aea3f9c22b2f05174 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 10V, Negative-QTOF | splash10-002f-1980000000-d1c8e15ec36f5d6cd39e | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 20V, Negative-QTOF | splash10-002f-9400000000-6ded983ef6b4abd0caa2 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Telbivudine 40V, Negative-QTOF | splash10-0006-9400000000-157f5aad418618113102 | 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 DB01265 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01265 | | 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 | DB01265 |
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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 | 140081 |
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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 | Telbivudine |
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METLIN ID | Not Available |
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PubChem Compound | 159269 |
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PDB ID | LLT |
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ChEBI ID | 63624 |
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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 | - Han SH: Telbivudine: a new nucleoside analogue for the treatment of chronic hepatitis B. Expert Opin Investig Drugs. 2005 Apr;14(4):511-9. [PubMed:15882124 ]
- Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. [PubMed:15985003 ]
- Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. [PubMed:16981973 ]
- Ruiz-Sancho A, Sheldon J, Soriano V: Telbivudine: a new option for the treatment of chronic hepatitis B. Expert Opin Biol Ther. 2007 May;7(5):751-61. [PubMed:17477811 ]
- Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [PubMed:17722961 ]
- Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. [PubMed:17724496 ]
- Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [PubMed:18069753 ]
- Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. doi: 10.1016/j.clinthera.2007.12.032. [PubMed:18201580 ]
- Cieslak J, Ausin C, Grajkowski A, Beaucage SL: Convenient and efficient approach to the permanent or reversible conjugation of RNA and DNA sequences with functional groups. Curr Protoc Nucleic Acid Chem. 2012 Sep;Chapter 4:Unit4.52. doi: 10.1002/0471142700.nc0452s50. [PubMed:22956458 ]
- Standring DN, Bridges EG, Placidi L, Faraj A, Loi AG, Pierra C, Dukhan D, Gosselin G, Imbach JL, Hernandez B, Juodawlkis A, Tennant B, Korba B, Cote P, Cretton-Scott E, Schinazi RF, Myers M, Bryant ML, Sommadossi JP: Antiviral beta-L-nucleosides specific for hepatitis B virus infection. Antivir Chem Chemother. 2001;12 Suppl 1:119-29. [PubMed:11594678 ]
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