化合物信息

ID:1133

基本信息

化学结构

分子式

C₁₀H₁₄N₂O₅

分子量

242.22856

精确质量

242.09027156

电荷

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

InChIKey

IQFYYKKMVGJFEH-CSMHCCOUSA-N

Canonic Smiles

OC[C@@H]1O[C@@H](C[C@H]1O)n1cc(C)c(=O)[nH]c1=O

Isomeric Smiles

O1[C@H](n2cc(c(=O)[nH]c2=O)C)C[C@@H](O)[C@@H]1CO

计算属性

JChem

LogD (pH = 7.4)

-1.12

LogD (pH = 5.5)

-1.12

Log P

-1.12

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

9.96

极化表面积

99.10

极化性

23.07

摩尔折射率

55.41

LOG S

-0.88

数据来源

学术数据

产品目录

数据来源

名称和标识

商标名

SebivoTyzeka

IUPAC传统名

telbivudine

别名

Beta-l-thymidineTelbivudineL-deoxythymidineL-DT2'-Deoxy-L-thymidineL-thymidineLDTEpavudinetelbivudineTelbivudin1-(2-Deoxy-beta-D-ribofuranosyl)-5-methyluracilThymidineSebivoTyzekaL-ThyMidine2'-Deoxy-L-thymidineBeta-l-thymidine1-(2-deoxy-beta-L-ribofuranosyl)-5-methyluracilLDTL-DTEpavudinebeta-L-2'-deoxythymidineL-thymidinetelbivudineL-deoxythymidine

IUPAC标准名

1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

API名称

Telbivudine

国际非专利药品(INN)

telbivudine

名称和标识

数据登录号

CAS号

3424-98-450-89-5

PubChem SID

16096459646508706135611174

PubChem CID

159269

MDL号

MFCD00006537

DrugBank ID

DB01265

PubMed文献链接

21586234211471872225710822093034222332552174852222174039214574392170320621670922216428142213270221040410

Reaxys Registry

CHEBI ID

SureChEMBL数据库

CHEMBL

PDB数据库

BKMS React数据库

BRENDA数据库

CompTox数据库

BRENDA Ligand数据库

维基百科标题

Drug Central Database

4,220

BindingDB数据库

50088372

MetaboLights数据库

MTBLS3950MTBLS2145MTBLS1693

ACToR数据库

3424-98-4

KEGG DRUG Database

D06675

数据登录号

化合物性质

理化性质

疏水性(logP)

-1.4

溶解度

Sparingly soluble in water (>20 mg/mL)

熔点

186-188°C

安全信息

保存条件

-20°C

产品相关信息

成盐信息

Free Base

纯度

97%

化合物性质

分子相关蛋白质

PDB Bank

3HP1

3QEO

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

Selleck Chemicals

S1651

Research Area: Infection
Biological Activity:
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 thymidine nucleoside analogue; it is the L-isomer of thymidine. It is taken once daily. [1]

DrugBank

DB01265

Drug Groups

approved; investigational

Description

Telbivudine 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.

Indication

For the treatment of chronic hepatitis B in adult and adolescent patients ≥16 years of age with evidence of viral replication and either evidence of persistent elevations in serum aminotransferases (ALT or AST) or histologically active disease.

Pharmacology

Telbivudine is a synthetic thymidine nucleoside analogue with activity against hepatitis B virus (HBV). Telbivudine is the unmodified β–L enantiomer of the naturally occurring nucleoside, thymidine. It undergoes phosphorylation via interaction with cellular kinases to form the active metabolite, telbivudine 5'-triphosphate.

Toxicity

There is no information on intentional overdose of telbivudine, but one subject experienced an unintentional and asymptomatic overdose. Healthy subjects who received telbivudine doses up to 1800 mg/day for 4 days had no increase in or unexpected adverse events. A maximum tolerated dose for telbivudine has not been determined.

Affected Organisms

Hepatitis B virus

Biotransformation

No metabolites of telbivudine were detected following administration of [14C]–telbivudine in humans. Telbivudine is not a substrate, or inhibitor of the cytochrome P450 (CYP450) enzyme system.

Absorption

Absorbed following oral administration. Telbivudine absorption and exposure were unaffected when a single 600–mg dose was administered with a high–fat (~55 g), high–calorie (~950 kcal) meal.

Half Life

Approximately 15 hours.

Protein Binding

In vitro binding of telbivudine to human plasma proteins is low (3.3%).

Elimination

Telbivudine is eliminated primarily by urinary excretion of unchanged drug.

Clearance

* 7.6 +/- 2.9 L/h [Normal renal function (Clcr>80 mL/min)]
* 5.0 +/- 1.2 L/h [Mild renal function impairement (Clcr=50-80 mL/min)]
* 2.6 +/- 1.2 L/h [Moderate renal function impairement (Clcr=30-49 mL/min)]
* 0.7 +/- 0.4 L/h [Severe renal function impairement (Clcr<30 mL/min)]

References

• Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. [Pubmed]

• Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [Pubmed]

• Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. [Pubmed]

• Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [Pubmed]

• 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]

• Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. [Pubmed]

• 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]

• Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. [Pubmed]

External Links

• [RxList]

• [Drugs.com]

ChEBI

CHEBI:63624

A pyrimidine 2'-deoxyribonucleoside that is the L-enantiomer of thymine. A synthetic thymidine nucleoside analogue with activity against HBV DNA polymerase.

描述信息

参考文献

PubChem文献

数据源提供

• Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. Pubmed

• Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. Pubmed

• Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. Pubmed

• Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. Pubmed

• Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. Pubmed

• 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

• 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

• Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. Pubmed

• http://en.wikipedia.org/wiki/Telbivudine

参考文献

生物活性

PubChem BioAssay

生物活性

导航

基本信息

计算属性

• RDKit

• JChem

数据来源

• 学术数据

• 产品目录

名称和标识

• 商标名

• IUPAC传统名

• 别名

• IUPAC标准名

• API名称

• 国际非专利药品(INN)

名称和标识

数据登录号

• CAS号

• PubChem SID

• PubChem CID

• MDL号

• DrugBank ID

• PubMed文献链接

• Reaxys Registry

• CHEBI ID

• SureChEMBL数据库

• CHEMBL

• PDB数据库

• BKMS React数据库

• BRENDA数据库

• CompTox数据库

• BRENDA Ligand数据库

• 维基百科标题

• Drug Central Database

• BindingDB数据库

• MetaboLights数据库

• ACToR数据库

• KEGG DRUG Database

数据登录号

化合物性质

• 理化性质

• 安全信息

• 产品相关信息

分子相关蛋白质

• PDB Bank

分子图谱

描述信息

• Selleck Chemicals

• DrugBank

• ChEBI

参考文献

• PubChem文献

• 数据源提供

生物活性

• PubChem BioAssay

商标名

SebivoTyzeka

IUPAC传统名

telbivudine

别名

IUPAC标准名

1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

API名称

Telbivudine

国际非专利药品(INN)

telbivudine

Reaxys Registry

CHEBI ID

SureChEMBL数据库

PDB数据库

BKMS React数据库

BRENDA数据库

CompTox数据库

BRENDA Ligand数据库

维基百科标题

Drug Central Database

4,220

BindingDB数据库

50088372

MetaboLights数据库

MTBLS3950MTBLS2145MTBLS1693

ACToR数据库

3424-98-4

KEGG DRUG Database

D06675

理化性质

疏水性(logP)

-1.4

溶解度

Sparingly soluble in water (>20 mg/mL)

熔点

186-188°C

安全信息

保存条件

-20°C

产品相关信息

成盐信息

Free Base

纯度

97%

Selleck Chemicals

S1651

DrugBank

DB01265

Drug Groups

approved; investigational

Description

Indication

Pharmacology

Toxicity

Affected Organisms

Hepatitis B virus

Biotransformation

No metabolites of telbivudine were detected following administration of [14C]–telbivudine in humans. Telbivudine is not a substrate, or inhibitor of the cytochrome P450 (CYP450) enzyme system.

Absorption

Absorbed following oral administration. Telbivudine absorption and exposure were unaffected when a single 600–mg dose was administered with a high–fat (~55 g), high–calorie (~950 kcal) meal.

Half Life

Approximately 15 hours.

Protein Binding

In vitro binding of telbivudine to human plasma proteins is low (3.3%).

Elimination

Telbivudine is eliminated primarily by urinary excretion of unchanged drug.

Clearance

References

• Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. [Pubmed]

• Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. [Pubmed]

• Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. [Pubmed]

• Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. [Pubmed]

• 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]

• Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. [Pubmed]

• 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]

• Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. [Pubmed]

External Links

• [RxList]

• [Drugs.com]

ChEBI

CHEBI:63624

A pyrimidine 2'-deoxyribonucleoside that is the L-enantiomer of thymine. A synthetic thymidine nucleoside analogue with activity against HBV DNA polymerase.

数据源提供

• Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. Pubmed

• Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. Pubmed

• Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. Pubmed

• Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. Pubmed

• Jones R, Nelson M: Novel anti-hepatitis B agents: A focus on telbivudine. Int J Clin Pract. 2006 Oct;60(10):1295-9. Pubmed

• 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

• 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

• Marcellin P, Asselah T, Boyer N: Treatment of chronic hepatitis B. J Viral Hepat. 2005 Jul;12(4):333-45. Pubmed

• http://en.wikipedia.org/wiki/Telbivudine