CAS 134678-17-4|Heptovir|Lamivudine|Zeffix|Epivir|3TC|lamivudine|4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one|Epivir-HBV|4-amino-1-((2R,5S)-2-(hydroxymethyl)-...

基本信息

化学结构

分子式

C₈H₁₁N₃O₃S

分子量

229.25624

精确质量

229.05211223

电荷

InChI

InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1

InChIKey

JTEGQNOMFQHVDC-NKWVEPMBSA-N

Canonic Smiles

Nc1ccn(c(=O)n1)[C@@H]1CS[C@@H](O1)CO

Isomeric Smiles

S1C[C@H](O[C@H]1CO)n1ccc(nc1=O)N

计算属性

JChem

LogD (pH = 7.4)

-1.10

LogD (pH = 5.5)

-1.10

Log P

-1.10

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

2.70

极化表面积

88.15

极化性

22.00

摩尔折射率

55.16

LOG S

-1.22

数据来源

名称和标识

别名

HeptovirLamivudineZeffixEpivir3TCEpivir-HBV4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-oneLamivudine2′,3′-Dideoxy-3′-thiacytidineVirolamLamivir(-)-2'-Deoxy-3'-thiacytidineβ-L-3'-Thia-2',3'-dideoxycytidineβ-L-2',3'-Dideoxy-3'-thiacytidineHepitecL-SddCEpivir HBV(-)-BCH 189Heptodin4-Amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone(2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinoneLamivudine [Usan:Ban:Inn](-)-2'-Deoxy-3'-thiacytidineLamivudinebeta-L-3'-Thia-2',3'-dideoxycytidinebeta-L-2',3'-Dideoxy-3'-thiacytidinelamivudine2',3'-Dideoxy-3'-thiacytidine3TC3'-Thia-2',3'-dideoxycytidine(-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine

IUPAC传统名

lamivudine 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

IUPAC标准名

4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

商标名

HepitecZeffixEpivir-HBVHeptovir3TCEpivir

API名称

Lamivudine

国际非专利药品(INN)

lamivudine

名称和标识

数据登录号

化合物性质

产品相关信息

成盐信息

Free Base

纯度

≥98% (HPLC)

95+%

Empirical Formula (Hill Notation)

C8H11N3O3S

质检报告

下载链接

应用领域

Potent antiviral agent

Active against hepatitis B virus and human immunodeficiency virus

药理学性质

生物活性机理

HIV reverse transcriptase inhibitor

化合物性质

分子相关蛋白质

PDB Bank

2NOA

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

DrugBank

DB00709

Drug Groups

approved; investigational

Description

A reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV).

Indication

For the treatment of HIV infection and chronic hepatitis B (HBV).

Pharmacology

Lamivudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV). Lamivudine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.

Affected Organisms

Human Immunodeficiency Virus

Hepatitis B virus

Biotransformation

The only detected metabolite of lamivudine is trans-sulfoxide.

Absorption

Lamivudine was rapidly absorbed after oral administration in HIV-infected patients. Absolute bioavailability in adults is 86% ± 16% for the tablet and 87% ± 13% for the oral solution.

Half Life

5 to 7 hours

Protein Binding

36%

Elimination

The primary routes of elimination of abacavir are metabolism by alcohol dehydrogenase to form the 5′-carboxylic acid and glucuronyl transferase to form the 5′-glucuronide. Lamivudine is excreted in human breast milk and into the milk of lactating rats.

Clearance

* Renal cl=280.4?+/-?75.2 mL/min [HIV-infected?patients given a single IV doses ranging from 0.25 to 8 mg/kg]

References

• Fox Z, Dragsted UB, Gerstoft J, Phillips AN, Kjaer J, Mathiesen L, Youle M, Katlama C, Hill A, Bruun JN, Clumeck N, Dellamonica P, Lundgren JD: A randomized trial to evaluate continuation versus discontinuation of lamivudine in individuals failing a lamivudine-containing regimen: the COLATE trial. Antivir Ther. 2006;11(6):761-70. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1706

Research Area: Infection
Biological Activity:
Lamivudine(Epivir) is a potent nucleoside analog reverse transcriptase inhibitor with an IC50 of 2.7 mM. [1] The pH-driven uptake of TEA by BBMV (pHin = 6.0, pHout = 7.5) was inhibited by lamivudine. The IC50 value (concentration resulting in 50% inhibition) for the concentration-dependent effect of lamivudine on TEA uptake by BBMV after 30 s was 2668 µM whereas IC50 values for cimetidine and trimethoprim were < 2.5 µM and < 25 µM, respectively. The early uptake of TEA by BLMV was also reduced significantly by lamivudine. The IC50 value for the concentration-dependent effect of lamivudine on uptake of TEA by BLMV at 30 s was > 25 mM, whereas the IC50 values for cimetidine and trimethoprim were 2116 µM and 445µM, respectively. [2]

Sigma Aldrich

L1295

Biochem/physiol Actions
Lamivudine is a potent nucleoside analog reverse transcriptase inhibitor (nRTI). It is an analogue of cytidine, and can inhibit both types (1 and 2) of HIV reverse transcriptase as well as the reverse transcriptase of hepatitis B. It needs to be phosphorylated to its triphosphate form before it is active. 3TC-triphosphate also inhibits cellular DNA polymerase.

TRC

L172500

Lamivudine is a potent nucleoside reverse transcriptase inhibitor. Antiviral. Lamivudine has been used for treatment of chronic hepatitis B.

ChEBI

CHEBI:63577

A monothioacetal that consists of cytosine having a (2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl moiety attached at position 1. An inhibitor of HIV-1 reverse transcriptase, it is used as an antiviral in the treatment of AIDS and hepatitis B.

描述信息

参考文献

PubChem文献

数据源提供

• Takubo T et al. J Pharm Pharmacol. 2000 May;52(5)

• Perry, C.M., et al.: Drugs, 53, 657 (1944)

• Morris, D.M., J. Pharm. Biomed. Anal., 12, 255 (1944)

• Nevens, B.F., et al.: Gastroenterology, 113, 1258 (1944)

• Beach, J.W. et al., J.O.C., 1991, 56, 6503; 1992, 57, 2217, (synth, bibl, pharmacol)

• Skalski, V. et al., J. Biol. Chem., 1993, 268, 23234, (pharmacol)

• van Leeuwen, R. et al., J. Infect. Dis., 1995, 171, 1166; 1438, (clin trials)

• Perry, C.M. et al., Drugs, 1997, 54, 657-680, (rev)

• Schinazi, R.F. et al., Antimicrob. Agents Chemother., 1992, 36, 672, (pharmacol)

• Chang, C.N. et al., J. Biol. Chem., 1992, 267, 22414, (pharmacol)

• Soudeyns, H. et al., Antimicrob. Agents Chemother., 1991, 35, 1386, (pharmacol)

• Storer, R. et al., Nucleosides Nucleotides, 1993, 12, 225, (synth, abs config)

• Jarvis, B. et al., Drugs, 1999, 58, 101-141

• Eur. Pat., 1992, Glaxo, 517 145; CA, 118, 191756p, (synth, cryst struct)

• Humber, D.C. et al., Tet. Lett., 1992, 33, 4625, (synth, bibl)

• Jeong, L.S. et al., J. Med. Chem., 1993, 36, 181; 2627, (synth, bibl, pharmacol, pmr, uv)

• Coates, J.A.V. et al., Antimicrob. Agents Chemother., 1992, 36, 202, (pharmacol)

• Harris, R.K. et al., J.C.S. Perkin 1, 1997, 2653-2659, (cryst struct, ir, cmr, pmr)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 622

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

lamivudine 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

IUPAC标准名

4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

商标名

HepitecZeffixEpivir-HBVHeptovir3TCEpivir

API名称

Lamivudine

国际非专利药品(INN)

lamivudine

分子相关蛋白质

PDB Bank

2NOA

描述信息

DrugBank

DB00709

Drug Groups

approved; investigational

Description

Indication

For the treatment of HIV infection and chronic hepatitis B (HBV).

Pharmacology

Affected Organisms

Human Immunodeficiency Virus

Hepatitis B virus

Biotransformation

The only detected metabolite of lamivudine is trans-sulfoxide.

Absorption

Lamivudine was rapidly absorbed after oral administration in HIV-infected patients. Absolute bioavailability in adults is 86% ± 16% for the tablet and 87% ± 13% for the oral solution.

Half Life

5 to 7 hours

Protein Binding

36%

Elimination

Clearance

* Renal cl=280.4?+/-?75.2 mL/min [HIV-infected?patients given a single IV doses ranging from 0.25 to 8 mg/kg]

References

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1706

Sigma Aldrich

L1295

TRC

L172500

Lamivudine is a potent nucleoside reverse transcriptase inhibitor. Antiviral. Lamivudine has been used for treatment of chronic hepatitis B.

ChEBI

CHEBI:63577

参考文献

PubChem文献

数据源提供

• Takubo T et al. J Pharm Pharmacol. 2000 May;52(5)

• Perry, C.M., et al.: Drugs, 53, 657 (1944)

• Morris, D.M., J. Pharm. Biomed. Anal., 12, 255 (1944)

• Nevens, B.F., et al.: Gastroenterology, 113, 1258 (1944)

• Beach, J.W. et al., J.O.C., 1991, 56, 6503; 1992, 57, 2217, (synth, bibl, pharmacol)

• Skalski, V. et al., J. Biol. Chem., 1993, 268, 23234, (pharmacol)

• van Leeuwen, R. et al., J. Infect. Dis., 1995, 171, 1166; 1438, (clin trials)

• Perry, C.M. et al., Drugs, 1997, 54, 657-680, (rev)

• Schinazi, R.F. et al., Antimicrob. Agents Chemother., 1992, 36, 672, (pharmacol)

• Chang, C.N. et al., J. Biol. Chem., 1992, 267, 22414, (pharmacol)

• Soudeyns, H. et al., Antimicrob. Agents Chemother., 1991, 35, 1386, (pharmacol)

• Storer, R. et al., Nucleosides Nucleotides, 1993, 12, 225, (synth, abs config)

• Jarvis, B. et al., Drugs, 1999, 58, 101-141

• Eur. Pat., 1992, Glaxo, 517 145; CA, 118, 191756p, (synth, cryst struct)

• Humber, D.C. et al., Tet. Lett., 1992, 33, 4625, (synth, bibl)

• Jeong, L.S. et al., J. Med. Chem., 1993, 36, 181; 2627, (synth, bibl, pharmacol, pmr, uv)

• Coates, J.A.V. et al., Antimicrob. Agents Chemother., 1992, 36, 202, (pharmacol)

• Harris, R.K. et al., J.C.S. Perkin 1, 1997, 2653-2659, (cryst struct, ir, cmr, pmr)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 622

生物活性

PubChem BioAssay

化合物性质

产品相关信息

成盐信息

Free Base

纯度

≥98% (HPLC)

95+%

Empirical Formula (Hill Notation)

C8H11N3O3S

质检报告

下载链接

应用领域

Potent antiviral agent

Active against hepatitis B virus and human immunodeficiency virus

药理学性质

生物活性机理

HIV reverse transcriptase inhibitor

化合物信息

ID:590