Compound: Telbivudine
SMILES: O=c1n(cc(C)c([nH]1)=O)[C@H]2O[C@@H](CO)[C@@H](C2)O
InChIKey: IQFYYKKMVGJFEH-CSMHCCOUSA-N
Synonyms: Telbivudine, 2'-Deoxy-L-thymidine, 3424-98-4, Epavudine, Tyzeka, L-Thymidine, Telbivudin, beta-L-Thymidine, L-Deoxythymidine, Sebivo, NV-02B, beta-L-2'-Deoxythymidine, LDT600, LDT-600, Telbivudina, 2OC4HKD3SF, 1-(2-Deoxy-beta-L-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione, CHEBI:63624, 1-(2-deoxy-beta-L-ribofuranosyl)-5-methyluracil, DTXSID30187813, 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione, 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-L-erythro-pentofuranosyl)-5-methyl-, NB 02B, beta L 2' Deoxythymidine, telbivudinum, 1-((2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione, 1-(2-Deoxy-beta-L-erythropentafuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione, RefChem:57765, DTXCID90110304, J05AF11, 1-(4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-5-methylpyrimidine-2,4-dione, L-dT, LdT, MFCD02683612, 1-((2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione, 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione, NV 02B, Telbivudine [USAN], 1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione, LLT, Tyzeka (TN), UNII-2OC4HKD3SF, Telbivudine (USAN/INN), 1-beta-l-ribofuranosylthymine, Telbivudine [USAN:INN:BAN], 1-[(2S,4R,5S)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione, Telbivudine (Standard), TELBIVUDINE [MI], TELBIVUDINE [INN], TELBIVUDINE [VANDF], TELBIVUDINE [MART.], TELBIVUDINE [WHO-DD], SCHEMBL124279, Telbivudine (Sebivo, Tyzeka), TELBIVUDINE [EMA EPAR], CHEMBL374731, Epavudine;L-Thymidine;NV 02B, orb1308383, Thymine, 1-(2-deoxy-beta-L-erythro-pentofuranosyl)-, HY-B0017R, Telbivudine, >=98% (HPLC), TELBIVUDINE [ORANGE BOOK], 1-(2-Deoxy-|A-L-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione, IQFYYKKMVGJFEH-CSMHCCOUSA-N, HY-B0017, BDBM50088372, EBC-11110, MSK160695, s1651, AKOS025117349, AC-5632, CCG-266887, CS-1934, DB01265, NM06240, NT02679, 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-b-L-erythro-pentofuranosyl)-5-methyl-, NCGC00346560-01, NCGC00346560-06, NCGC00346560-12, AS-35209, BP-58605, SY029169, NS00001939, SW220236-1, 1-(2-Deoxy-?-L-erythro-pentofuranosyl)thymine, D06675, EN300-123027, AB01274717-01, AB01274717_02, F091804, Q413621, BRD-K15976406-001-01-7, BRD-K15976406-001-03-3, Thymine, 1-(2-deoxy-.beta.-L-erythro-pentofuranosyl)-, Z1546610488, 1-[(2R,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione, 2,4(1H,3H)-PYRIMIDINEDIONE,1-(2-DEOXY-.BETA.-L-ERYTHRO-PENTOFURANOSYL)-5-METHYL-
Theoretical properties:
molecular_formula: C10H14N2O5
molecular_weight: 242.23 g/mol
exact_mass: 242.09027155 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 17
topological_polar_surface_area: 99.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: Sparingly soluble in water (>20 mg/mL)
Descriptions:
{"pubchem": "Telbivudine is a pyrimidine 2'-deoxyribonucleoside that is the L-enantiomer of thymine. A synthetic thymidine nucleoside analogue with activity against HBV DNA polymerase. It has a role as an antiviral drug and an EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor. It is functionally related to a thymine. It is an enantiomer of a thymidine.", "chebi": "A pyrimidine 2'-deoxyribonucleoside that is the <small>L</small>-enantiomer of thymine. A synthetic thymidine nucleoside analogue with activity against HBV DNA polymerase.", "chembl": "TELBIVUDINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Telbivudine is an antiviral drug used in the treatment of hepatitis B infection. It is marketed by Swiss pharmaceutical company Novartis under the trade names Sebivo (European Union) and Tyzeka (United States). Clinical trials have shown it to be significantly more effective than lamivudine or adefovir, and less likely to cause resistance. However, HBV signature resistance mutation M204I (a change from methionine to isoleucine at position 204 in the reverse transcriptase domain of the hepatitis B polymerase)  or L180M+M204V have been associated with Telbivudine resistance.\nTelbivudine is a synthetic thymidine \u03b2-L-nucleoside analogue; it is the L-isomer of thymidine. Telbivudine impairs hepatitis B virus (HBV) DNA replication by leading to chain termination. It differs from the natural nucleotide only with respect to the location of the sugar and base moieties, taking on an levorotatory configuration versus a dextrorotatory configuration as do the natural deoxynucleosides. It is taken orally in a dose of 600 mg once daily with or without food.\nTelbivudine has no in vitro activity against HIV-1, and in a case-series of three HIV-HBV co-infected patients, telbivudine did not produce sustained HIV-1 virologic suppression or induce any resistance mutations in HIV-1.\nPhase III clinical trials suggested that telbivudine put patients at greater risk for myopathy and peripheral neuropathy than the comparator drug lamivudine.  FDA required a required a risk evaluation and mitigation strategy (REMS) aiming to increase awareness of peripheral neuropathy by requiring distribution of a medication guide.\nIn 2016, Novartis posted a discontinuation notice.  Efficacy or safety concerns were not cited as rationale for discontinuation, but rather \"availability of alternative medications\"; presumably this refers to tenofovir disoproxil, which became available as a generic medication in 2017, and is a safe and effective treatment for chronic HBV infection.\n\n"}