Telbivudine: Difference between revisions

Telbivudine
Clinical data
Trade names	Tyzeka
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 FDA: Tyzeka;
Routes of; administration	Oral
ATC code	J05AF11 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Protein binding	Low (3.3% in vitro)
Metabolism	Nil
Elimination half-life	40 to 49 hours (terminal phase)
Excretion	Renal
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	242.23 g/mol 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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Revision as of 04:22, 16 July 2016

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 (Europe) 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 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.

References

^ 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.
^ 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. PMID 18094378.
^ 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.
^ http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2762437/
^ Safety and efficacy of telbivudine for the treatment of chronic hepatitis B. "NCBI". Retrieved 16 July 2016.

External links

Tyzeka official website run by Novartis Pharmaceuticals Corporation
Telbivudine entry in RxList
Sebivo Summary of Product Characteristics (from the EMEA website)

This antiinfective drug article is a stub. You can help Wikipedia by expanding it.

[Lai1-1] 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.

[NEJM-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. 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] ttp://www.ncbi.nlm.nih.gov/pmc/articles/PMC2762437/

[5] Safety and efficacy of telbivudine for the treatment of chronic hepatitis B. "NCBI". Retrieved 16 July 2016.

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 '''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''' (Europe) and '''Tyzeka''' (United States). [[Clinical trial]]s have shown it to be [[statistical significance|significantly]] more effective than [[lamivudine]] or [[adefovir]], and less likely to cause resistance.<ref name=Lai1>{{cite journal  |vauthors=Lai CL, Leung N, Teo EK, etal |title=A 1-year trial of telbivudine, lamivudine, and the combination in patients with hepatitis B e antigen-positive chronic hepatitis B |journal=Gastroenterology |volume=129 |issue=2 |pages=528–36 |year=2005 |pmid=16083710 |doi=10.1016/j.gastro.2005.05.053}}</ref><ref name=NEJM>{{cite journal  |vauthors=Lai CL, Gane E, Liaw YF, etal |title=Telbivudine versus lamivudine in patients with chronic hepatitis B |journal=[[New England Journal of Medicine|N Engl J Med]] |volume=357 |issue=25 |pages=2576–88 |year=2007 |pmid=18094378 |doi=10.1056/NEJMoa066422}}</ref><ref>{{cite journal  |vauthors=Chan HL, Heathcote EJ, Marcellin P, etal |title=Treatment of hepatitis B e antigen positive chronic hepatitis with telbivudine or adefovir: a randomized trial |journal=[[Annals of Internal Medicine|Ann Intern Med]] |volume=147 |issue=11 |pages=745–54 |date=4 December 2007|pmid=17909201 |url=http://www.annals.org/cgi/content/full/147/11/745 |doi=10.7326/0003-4819-147-11-200712040-00183}}</ref> 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.<ref>http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2762437/</ref>
-Telbivudine is a synthetic [[thymidine]] [[β-L-nucleoside analogue]]; it is the [[Stereoisomerism|<small>L</small>-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. <ref>http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2762437/</ref>It is taken orally in a dose of 600 mg once daily with or without food.
+Telbivudine is a synthetic [[thymidine]] [[β-L-nucleoside analogue]]; it is the [[Stereoisomerism|<small>L</small>-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.<ref>{{cite web|last1=Safety and efficacy of telbivudine for the treatment of chronic hepatitis B|title=NCBI|url=http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2762437/|accessdate=16 July 2016}}</ref> It is taken orally in a dose of 600 mg once daily with or without food.
 ==References==