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3424-98-4 分子结构
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1-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

ChemBase编号:1133
分子式:C10H14N2O5
平均质量:242.22856
单一同位素质量:242.09027156
SMILES和InChIs

SMILES:
O1[C@H](n2cc(c(=O)[nH]c2=O)C)C[C@@H](O)[C@@H]1CO
Canonical SMILES:
OC[C@@H]1O[C@@H](C[C@H]1O)n1cc(C)c(=O)[nH]c1=O
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

引用这个纪录

CBID:1133 http://www.chembase.cn/molecule-1133.html

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名称和登记号

名称和登记号

名称 登记号
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
IUPAC传统名
telbivudine
商标名
Tyzeka
Sebivo
别名
2'-Deoxy-L-thymidine
Beta-l-thymidine
Epavudine
L-DT
LDT
Telbivudin
L-deoxythymidine
L-thymidine
telbivudine
Telbivudine
1-(2-Deoxy-beta-D-ribofuranosyl)-5-methyluracil
Thymidine
Tyzeka
Sebivo
L-ThyMidine
CAS号
3424-98-4
50-89-5
MDL号
MFCD00006537
PubChem SID
46508706
160964596
PubChem CID
159269

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 8.960321  质子受体
质子供体 LogD (pH = 5.5) -1.1192024 
LogD (pH = 7.4) -1.1307083  Log P -1.1190536 
摩尔折射率 55.412 cm3 极化性 22.001661 Å3
极化表面积 99.1 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -1.32  LOG S -0.56 
溶解度 6.68e+01 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
Sparingly soluble in water (>20 mg/mL) expand 查看数据来源
熔点
186-188°C expand 查看数据来源
疏水性(logP)
-1.4 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
纯度
97% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals
DrugBank -  DB01265 external link
Item Information
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
Selleck Chemicals -  S1651 external link
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]

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Keam SJ: Telbivudine. Drugs. 2007;67(13):1917-29. Pubmed
  • Matthews SJ: Telbivudine for the management of chronic hepatitis B virus infection. Clin Ther. 2007 Dec;29(12):2635-53. Pubmed
  • Dusheiko G, Danta M: Telbivudine for the treatment of chronic hepatitis B. Drugs Today (Barc). 2007 May;43(5):293-304. 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
  • Amarapurkar DN: Telbivudine: a new treatment for chronic hepatitis B. World J Gastroenterol. 2007 Dec 14;13(46):6150-5. Pubmed
  • http://en.wikipedia.org/wiki/Telbivudine
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专利

专利

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