Telbivudine

Base Information

• Chemical Name: Telbivudine
• CAS No.: 3424-98-4
• Molecular Formula: C₁₀H₁₄N₂O₅
• Molecular Weight: 242.232
• Hs Code.: 29349990
• European Community (EC) Number: 608-961-3
• UNII: 2OC4HKD3SF
• DSSTox Substance ID: DTXSID30187813
• Nikkaji Number: J515.502I
• Wikipedia: Telbivudine
• Wikidata: Q413621
• NCI Thesaurus Code: C66584
• Metabolomics Workbench ID: 43471
• ChEMBL ID: CHEMBL374731
• Mol file: 3424-98-4.mol

Synonyms:1-(2-deoxy-beta-L-erythropentafuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione;beta L 2' Deoxythymidine;beta-L-2'-deoxythymidine;telbivudin;telbivudine;Tyzeka

Chemical Property of Telbivudine

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 188-190 °C
• PKA: 9.55±0.10(Predicted)
• PSA: 104.55000
• Density: 1.452 g/cm³
• LogP: -1.51430
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: soluble10mg/mL (clear solution)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 242.09027155
• Heavy Atom Count: 17
• Complexity: 381

Purity/Quality:

99% ^*data from raw suppliers

Telbivudine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@@H]2C[C@H]([C@@H](O2)CO)O
• Recent ClinicalTrials: Treatment of Hepatitis B Virus (HBV) Before Beginning Anti-HIV Drugs in Patients With Both HBV and HIV
• Recent EU Clinical Trials: A Proof-of-concept study to investigate the Efficacy of Telbivudine Over Placebo in patients with Parvovirus-associated Inflammatory Cardiomyopathy
• Description: Telbivudine is a b-L-thymidine nucleoside analog launched for the once-daily oral treatment of chronic hepatitis B virus (HBV) infection. It is the fourth nucleoside or nucleotide analog to be marketed for this indication. The previous drugs from this class include lamivudine, a deoxythiacytosine analog, adefovir, a nucleotide analog, and entecavir, a guanosine analog. Adefovir, entecavir, and telbivudine are specifically indicated for HBV, whereas lamivudine is indicated for both HBV and HIV infections. Telbivudine is efficiently phosphorylated by cellular kinases to the active triphosphate derivative, which inhibits HBV DNA polymerase by competing with the natural substrate, thymidine- 5’-triphosphate.
• Uses: Nucleoside analog; specific inhibitor of hepatitis B virus (HBV) replication. Antiviral. Nucleoside analog; specific inhibitor of hepatitis B virus (HBV) replication. Antiviral Telbivudine(Tyzeka, Sebivo) is an antiviral drug used in the treatment of hepatitis B infection. Clinical trials have shown it to be significantly more effective than lamivudine or adefovir, and less likely to cause resistance. Telbivudine is a synthetic

Technology Process of Telbivudine

There total 25 articles about Telbivudine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1-(2-deoxy-3,5-di-p-toluoyl-β-L-ribose)-5-methyluracil (3056-13-1) → C10H14N2O5 (50-89-5,3424-98-4,4449-43-8,4781-17-3,16053-52-4,36646-86-3,39131-66-3,68224-82-8,128112-70-9,131682-41-2,137121-87-0,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With methanol; sodium methylate; at 45 - 50 ℃;

Reference yield: 93.4%

3',5'-di-O-acetyl-β-L-thymidine (433733-94-9) → C10H14N2O5 (50-89-5,3424-98-4,4449-43-8,4781-17-3,16053-52-4,36646-86-3,39131-66-3,68224-82-8,128112-70-9,131682-41-2,137121-87-0,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With ammonia; In methanol; at 6 ℃; for 72h;

Reference yield: 90.0%

3',5'-di-O-levulinoyl-β-L-thymidine (793716-98-0) → C10H14N2O5 (50-89-5,3424-98-4,4449-43-8,4781-17-3,16053-52-4,36646-86-3,39131-66-3,68224-82-8,128112-70-9,131682-41-2,137121-87-0,28854-96-8,3545-96-8,50-88-4) + 3'-O-levulinoyl-β-L-thymidine

Guidance literature:

With Candida antarctica lipase B; phosphate buffer; In 1,4-dioxane; at 30 ℃; for 28.5h; pH=7;

DOI:10.1021/ol048502v

upstream raw materials:

2',3',5'-tri-O-benzoyl-5-methyl-L-uridine

3',5'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-L-thymidine

3',5'-di-O-levulinoyl-β-L-thymidine

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose

Downstream raw materials:

S-methyl-L-cysteine

3-methylthymidine

5'-benzoylthymidine

1-((2S,4R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Refernces

• 1、 -. "Synthesis method of beta-thymidine". . . Retrieved 2017/08/14.
• 2、 -. "Method for preparing telbivudine". Paragraph 0052; 0053; 0054. . Retrieved 2016/10/09.