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)-...

General Information

Structure

Molecular Formula

C₈H₁₁N₃O₃S

Molecular Mass

229.25624

Exact Mass

229.05211223

Charge

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

Calculated Properties

JChem

LogD (pH = 7.4)

-1.10

LogD (pH = 5.5)

-1.10

Log P

-1.10

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

2.70

Polar Surface Area

88.15

Polarizability

22.00

Molar Refractivity

55.16

LOG S

-1.22

Data Source

Names and Identifiers

Synonyms

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 Traditional name

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

IUPAC name

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

Brand Name

HepitecZeffixEpivir-HBVHeptovir3TCEpivir

API Name

Lamivudine

International Nonproprietary Name (INN)

lamivudine

Names and Identifiers

Registration numbers

Properties

Product Information

Salt Data

Free Base

Purity

≥98% (HPLC)

95+%

Empirical Formula (Hill Notation)

C8H11N3O3S

Certificate of Analysis

Download link

Application(s)

Potent antiviral agent

Active against hepatitis B virus and human immunodeficiency virus

Pharmacology Properties

Mechanism of Action

HIV reverse transcriptase inhibitor

Properties

Related Proteins

PDB Bank

2NOA

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

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

IUPAC name

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

Brand Name

HepitecZeffixEpivir-HBVHeptovir3TCEpivir

API Name

Lamivudine

International Nonproprietary Name (INN)

lamivudine

Related Proteins

PDB Bank

2NOA

Molecule Details

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

References

PubChem Literature

From Data Sources

• 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)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Bioactivity

PubChem BioAssay

Properties

Product Information

Salt Data

Free Base

Purity

≥98% (HPLC)

95+%

Empirical Formula (Hill Notation)

C8H11N3O3S

Certificate of Analysis

Download link

Application(s)

Potent antiviral agent

Active against hepatitis B virus and human immunodeficiency virus

Pharmacology Properties

Mechanism of Action

HIV reverse transcriptase inhibitor

Molecule

ID:590