Telbivudine

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.[1][2][3] 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.[4]

Telbivudine

Clinical data
Trade names	Tyzeka, Sebivo
Other names	1-(2-deoxy-β-L-ribofuranosyl)-5-methyluracil β-L-2-deoxythymidine β-L-thymidine (LdT) 1-[(2S,4R,5S)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
AHFS/Drugs.com	Monograph
MedlinePlus	a607045
License data	EU EMA: by INN US DailyMed: Telbivudine
Pregnancy category	AU: B1
Routes of administration	By mouth
ATC code	J05AF11 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only EU: Rx-only
Pharmacokinetic data
Protein binding	Low (3.3% in vitro)
Metabolism	Nil
Elimination half-life	40 to 49 hours (terminal phase)
Excretion	Kidney
Identifiers
IUPAC name 1-(2-deoxy-β-L-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
CAS Number	3424-98-4
PubChem CID	159269
DrugBank	DB01265
ChemSpider	140081
UNII	2OC4HKD3SF
ChEMBL	ChEMBL374731
CompTox Dashboard (EPA)	DTXSID30187813
ECHA InfoCard	100.125.511
Chemical and physical data
Formula	C10H14N2O5
Molar mass	242.231 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C/1NC(=O)N(\C=C\1C)[C@H]2O[C@H]([C@H](O)C2)CO
InChI 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 Key:IQFYYKKMVGJFEH-CSMHCCOUSA-N
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Telbivudine is a synthetic thymidine β-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.[5] It is taken orally in a dose of 600 mg once daily with or without food.

In 2016, Novartis posted a discontinuation notice for Tyzeka.[6][7]

References

1. Lai CL, Leung N, Teo EK, et al. (2005). "A 1-year trial of telbivudine, lamivudine, and the combination in patients with hepatitis B e antigen-positive chronic hepatitis B". Gastroenterology. 129 (2): 528–36. doi:10.1016/j.gastro.2005.05.053. PMID 16083710.
2. Lai CL, Gane E, Liaw YF, et al. (2007). "Telbivudine versus lamivudine in patients with chronic hepatitis B". N Engl J Med. 357 (25): 2576–88. doi:10.1056/NEJMoa066422. hdl:10722/57525. PMID 18094378.
3. Chan HL, Heathcote EJ, Marcellin P, et al. (4 December 2007). "Treatment of hepatitis B e antigen positive chronic hepatitis with telbivudine or adefovir: a randomized trial". Ann Intern Med. 147 (11): 745–54. doi:10.7326/0003-4819-147-11-200712040-00183. PMID 17909201.
4. Osborn MK (2009). "Safety and efficacy of telbivudine for the treatment of chronic hepatitis B". Ther Clin Risk Manag. 5: 789–98. doi:10.2147/tcrm.s5318. PMC 2762437. PMID 19851526.
5. Osborn MK. "Safety and efficacy of telbivudine for the treatment of chronic hepatitis B". Ther Clin Risk Manag. 5: 789–98. PMC 2762437. PMID 19851526.
6. "HBV drug Tyzeka discontinued". www.healio.com. Retrieved 2021-01-11.
7. "FDA: Hepatitis B Drug Discontinued". MPR. 2016-10-05. Retrieved 2021-01-11.

External links

• "Telbivudine". Drug Information Portal. U.S. National Library of Medicine.