Identification

Name
Lamivudine
Accession Number
DB00709
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).

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 229.256
Monoisotopic: 229.052111923
Chemical Formula
C8H11N3O3S
Synonyms
  • (-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine
  • (-)-2'-Deoxy-3'-thiacytidine
  • 2',3'-Dideoxy-3'-thiacytidine
  • 3'-Thia-2',3'-dideoxycytidine
  • 3TC
  • beta-L-2',3'-Dideoxy-3'-thiacytidine
  • beta-L-3'-Thia-2',3'-dideoxycytidine
  • Lamivudin
  • Lamivudina
  • Lamivudine
  • Lamivudinum
External IDs
  • BCH 189, (-)-
  • GR 109714X
  • GR-109714X

Pharmacology

Indication

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

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Lamivudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV) to disrupt viral DNA synthesis. When phosphorylated, lamivudine can form active metabolites that compete for incorporation into viral DNA. Via DNA incorporation, lamivudine metabolites competitively inhibit the activity of the HIV reverse transcriptase enzyme and act as a chain terminator of DNA synthesis. Due to the lack of a 3'-OH group, incorporated nucleoside analogues prevent the formation of a 5' to 3' phosphodiester linkage that is essential for DNA chain elongation.

Mechanism of action

Lamivudine is a synthetic nucleoside analogue and is phosphorylated intracellularly to its active 5'-triphosphate metabolite, lamivudine triphosphate (L-TP). This nucleoside analogue is incorporated into viral DNA by HIV reverse transcriptase and HBV polymerase, resulting in DNA chain termination.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
ADNA
adduct
Humans
AProtein P
inhibitor
HBV-F
Absorption

Lamivudine was rapidly absorbed after oral administration in HIV-infected patients. Absolute bioavailability in 12 adult patients was 86% ± 16% (mean ± SD) for the 150-mg tablet and 87% ± 13% for the oral solution. The peak serum lamivudine concentration (Cmax) was 1.5 ± 0.5 mcg/mL when an oral dose of 2 mg/kg twice a day was given to HIV-1 patients. When given with food, absorption is slower, compared to the fasted state.

Volume of distribution

Apparent volume of distribution, IV administration = 1.3 ± 0.4 L/kg. Volume of distribution was independent of dose and did not correlate with body weight.

Protein binding

<36% bound to plasma protein.

Metabolism

Metabolism of lamivudine is a minor route of elimination. In man, the only known metabolite of lamivudine is the trans-sulfoxide metabolite. This biotransformation is catalyzed by sulfotransferases.

Hover over products below to view reaction partners

Route of elimination

The majority of lamivudine is eliminated unchanged in urine by active organic cationic secretion. 5.2% ± 1.4% (mean ± SD) of the dose was excreted as the trans-sulfoxide metabolite in the urine. Lamivudine is excreted in human breast milk and into the milk of lactating rats.

Half-life

5 to 7 hours (healthy or HBV-infected patients)

Clearance
  • Renal clearance = 199.7 ± 56.9 mL/min [300 mg oral dose, healthy subjects]
  • Renal clearance = 280.4 ± 75.2 mL/min [single IV dose, HIV-1-infected patients]
  • Total clearance = 398.5 ± 69.1 mL/min [HIV-1-infected patients]
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

The most common reported adverse reactions (incidence ≥15%) in adults were headache, nausea, malaise and fatigue, nasal signs and symptoms, diarrhea, and cough.

Affected organisms
  • Human Immunodeficiency Virus
  • Hepatitis B virus
Pathways
PathwayCategory
Lamivudine Metabolism PathwayDrug metabolism
Lamivudine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbemaciclibAbemaciclib may decrease the excretion rate of Lamivudine which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Lamivudine which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Lamivudine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Lamivudine which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Lamivudine which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Lamivudine which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Lamivudine which could result in a higher serum level.
AcipimoxThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Acipimox.
AclidiniumLamivudine may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineLamivudine may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with or without food. Food delays drug absorption, but not to a clinically significant extent.

Products

Product Images
International/Other Brands
Amilitrap (Dosa) / Antiheb (Mebiphar) / Avilam (Beximco) / Avolam (Ranbaxy Laboratories) / Epivir-HBV (GlaxoSmithKline) / Flamivud (Flamingo Pharmacueticals) / Ganvirel (Ivax) / Hepavir (Square) / Hepitec (GlaxoSmithKline) / Heptavir (Hetero) / Heptodin (GlaxoSmithKline) / Heptodine (GlaxoSmithKline) / Lamda (Cadila) / Lamibergen (Paylos) / Lamidac (Zydus) / Lamitec (Zifam India) / Lamivir (Incepta) / Zeffix (GlaxoSmithKline)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
3tcTabletOralViiV Healthcare ULC2003-09-09Not applicableCanada flag
3tcSolutionOralViiV Healthcare ULC1995-12-31Not applicableCanada flag
3tcTabletOralViiV Healthcare ULC1995-12-31Not applicableCanada flag
CombivirTablet, film coated150 mg/1OralRemedy Repack2013-03-122014-03-12US flag00173 0595 00 nlmimage10 10230838
EpivirTablet150 mg/1OralRemedy Repack2011-02-032012-10-18US flag
EpivirTablet, film coated150 mgOralViiV Healthcare ULC1996-08-08Not applicableEU flag
EpivirTablet, film coated300 mg/1OralViiV Healthcare Company2010-10-04Not applicableUS flag49702 0204 13 nlmimage10 7e193f29
EpivirTablet, film coated150 mg/1OralKAISER FOUNDATION HOSPITALS2011-03-152013-03-31US flag
EpivirTablet, film coated300 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUS flag
EpivirTablet, film coated150 mg/1Oralbryant ranch prepack1995-11-212015-06-16US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-lamivudineTabletOralApotex Corporation2012-05-18Not applicableCanada flag
Apo-lamivudineTabletOralApotex Corporation2012-05-18Not applicableCanada flag
Apo-lamivudine HbvTabletOralApotex Corporation2012-09-21Not applicableCanada flag
Auro-lamivudineTabletOralAuro Pharma Inc2013-10-162013-10-16Canada flag
Auro-lamivudineTabletOralAuro Pharma Inc2013-10-162013-10-16Canada flag
LamivudineTablet, film coated150 mg/1OralArise Pharmaceuticals Llc2019-04-09Not applicableUS flag
LamivudineTablet, film coated150 mg/1OralGolden State Medical Supply, Inc.2011-12-02Not applicableUS flag
LamivudineTablet, film coated150 mg/1OralREMEDYREPACK INC.2019-03-042020-06-01US flag
LamivudineTablet, film coated150 mg/1OralStrides Pharma Science Limited2018-10-19Not applicableUS flag
LamivudineTablet150 mg/1OralEci Pharmaceuticals Llc2018-06-15Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralREMEDYREPACK INC.2017-08-282020-05-04US flag
Abacavir and lamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralZydus Pharmaceuticals (USA) Inc.2019-03-14Not applicableUS flag
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralBurel Pharma2017-03-28Not applicableUS flag
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralAurobindo Pharma Limited2017-03-28Not applicableUS flag
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralTeva Pharmaceuticals USA, Inc.2016-09-29Not applicableUS flag
Abacavir and lamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralCadila Healthcare Limited2019-03-14Not applicableUS flag
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralLupin Pharmaceuticals, Inc.2017-03-28Not applicableUS flag
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralAv Kare, Inc.2018-02-21Not applicableUS flag
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralBurel Pharma2019-11-15Not applicableUS flag
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir sulfate (600 mg/1)Tablet, film coatedOralAurobindo Pharma Limited2018-11-15Not applicableUS flag

Categories

ATC Codes
J05AR27 — Lamivudine, tenofovir disoproxil and dolutegravirJ05AR02 — Lamivudine and abacavirJ05AR25 — Lamivudine and dolutegravirJ05AR11 — Lamivudine, tenofovir disoproxil and efavirenzJ05AR07 — Stavudine, lamivudine and nevirapineJ05AR01 — Zidovudine and lamivudineJ05AR13 — Lamivudine, abacavir and dolutegravirJ05AR12 — Lamivudine and tenofovir disoproxilJ05AR24 — Lamivudine, tenofovir disoproxil and doravirineJ05AR04 — Zidovudine, lamivudine and abacavirJ05AR16 — Lamivudine and raltegravirJ05AR05 — Zidovudine, lamivudine and nevirapineJ05AF05 — Lamivudine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 3'-thia pyrimidine nucleosides. These are nucleoside analogues with a structure that consists of a pyrimidine base, which is N-substituted at the 1-position with a 3'-thia derivative (1,3-oxazolidine) of the ribose moiety that is characteristic of nucleosides.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Nucleoside and nucleotide analogues
Sub Class
3'-thia pyrimidine nucleosides
Direct Parent
3'-thia pyrimidine nucleosides
Alternative Parents
Hydroxypyrimidines / Hydropyrimidines / Oxathiolanes / Monothioacetals / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds
show 1 more
Substituents
3'-thia pyrimidine nucleoside / Alcohol / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Hydroxypyrimidine / Monothioacetal / Organic nitrogen compound
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
primary alcohol, oxacycle, monothioacetal (CHEBI:63577)

Chemical Identifiers

UNII
2T8Q726O95
CAS number
134678-17-4
InChI Key
JTEGQNOMFQHVDC-NKWVEPMBSA-N
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
IUPAC Name
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
SMILES
NC1=NC(=O)N(C=C1)[[email protected]@H]1CS[[email protected]](CO)O1

References

Synthesis Reference

Jinliang LI, Feng LV, "PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE." U.S. Patent US20100249409, issued September 30, 2010.

US20100249409
General References
  1. 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:17310820]
Human Metabolome Database
HMDB0014847
KEGG Drug
D00353
KEGG Compound
C07065
PubChem Compound
60825
PubChem Substance
46507855
ChemSpider
54812
BindingDB
50366817
RxNav
68244
ChEBI
63577
ChEMBL
CHEMBL141
ZINC
ZINC000000012346
Therapeutic Targets Database
DAP000167
PharmGKB
PA450163
PDBe Ligand
3TC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Lamivudine
AHFS Codes
  • 08:18.08.20 — Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
PDB Entries
2noa
FDA label
Download (310 KB)
MSDS
Download (57.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection / Solid Organ Transplant1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Proteinuria1
4CompletedBasic ScienceCardiovascular Heart Disease / Dyslipidemia / Glucose Metabolism Disorders / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Metabolic Diseases1
4CompletedDiagnosticCardiovascular Heart Disease / HIV-Associated Lipodystrophy Syndrome1
4CompletedDiagnosticHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedOtherHuman Immunodeficiency Virus (HIV) Infections2
4CompletedPreventionCentral Nervous System Diseases / Dementias / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionChronic Infection / Hepatitis B Infection / Viral sepsis1
4CompletedPreventionComplications / Hepatitis B Chronic Infection / Late Pregnancy / Transmission1

Pharmacoeconomics

Manufacturers
  • Viiv healthcare co
  • Glaxosmithkline
Packagers
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Cardinal Health
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • GlaxoSmithKline Inc.
  • Kaiser Foundation Hospital
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Rebel Distributors Corp.
  • Remedy Repack
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Tya Pharmaceuticals
  • ViiV Healthcare ULC
Dosage Forms
FormRouteStrength
TabletOral
SolutionOral
Tablet, film coatedOral600 mg
TabletOral60 mg
Tablet, coatedOral400 mg
TabletOral30 mg
Tablet, coatedOral
Tablet, film coatedOral
SolutionOral10 mg/ml
SolutionOral10 mg/1mL
Syrup10 mg/1mL
Tablet150 MG
TabletOral150 mg/1
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral150 mg
Tablet, film coatedOral300 mg
Tablet, film coatedOral300 mg/1
Tablet300 mg
SolutionOral5 mg/1mL
Tablet, film coatedOral100 mg/1
Tablet
Tablet, coatedOral150 mg
Tablet, coatedOral100 MG
TabletOral300 mg/1
TabletOral
Tablet, film coatedOral100 mg
Tablet, coated100 mg
Tablet, film coatedOral
SolutionOral1 g
Tablet, film coated100 mg
Tablet, film coated150 mg
Tablet, coated300 mg
Tablet, coatedOral300 mg
Tablet, solubleOral30 mg
Tablet, coatedOral600 mg
Tablet, film coatedOral50 MG
Tablet, coatedOral50 mg
TabletOral300 mg
SolutionOral5 MG/ML
TabletOral100 MG
TabletOral150 mg
Prices
Unit descriptionCostUnit
Epzicom 600-300 mg tablet37.21USD tablet
Epzicom tablet35.78USD tablet
Epivir 300 mg tablet15.57USD tablet
Epivir hbv 100 mg tablet13.94USD tablet
Epivir 150 mg tablet7.79USD tablet
Epivir 10 mg/ml Solution0.53USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7119202No2006-10-102009-08-08US flag
CA2070230No2004-08-032012-06-02Canada flag
CA2100269No1999-02-232012-01-03Canada flag
US9242986No2016-01-262029-10-08US flag
US5905082Yes1999-05-182016-11-18US flag
US6004968Yes1999-12-212018-09-20US flag
US6294540Yes2001-09-252018-11-14US flag
US7217713Yes2007-05-152023-04-21US flag
US7435734Yes2008-10-142023-04-21US flag
US7754731Yes2010-07-132029-09-11US flag
US7169780Yes2007-01-302024-04-03US flag
US6417191Yes2002-07-092016-09-28US flag
US8129385No2012-03-062027-10-05US flag
US7820660No2010-10-262023-04-25US flag
US8486975No2013-07-162031-10-07US flag
US10603282No2016-11-292036-11-29US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)160-162 °CNot Available
water solubility70 mg/mlNot Available
logP-1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.76 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)14.29ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.15 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.16 m3·mol-1ChemAxon
Polarizability21.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9932
Blood Brain Barrier+0.9792
Caco-2 permeable-0.7147
P-glycoprotein substrateNon-substrate0.7523
P-glycoprotein inhibitor INon-inhibitor0.9561
P-glycoprotein inhibitor IINon-inhibitor0.9803
Renal organic cation transporterNon-inhibitor0.8646
CYP450 2C9 substrateNon-substrate0.7476
CYP450 2D6 substrateNon-substrate0.8393
CYP450 3A4 substrateNon-substrate0.6393
CYP450 1A2 substrateNon-inhibitor0.8687
CYP450 2C9 inhibitorNon-inhibitor0.7933
CYP450 2D6 inhibitorNon-inhibitor0.9206
CYP450 2C19 inhibitorNon-inhibitor0.8282
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.887
Ames testAMES toxic0.6341
CarcinogenicityNon-carcinogens0.782
BiodegradationNot ready biodegradable0.9698
Rat acute toxicity2.1348 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9834
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Not Available
Gene Name
pol
Uniprot ID
Q72547
Uniprot Name
Reverse transcriptase/RNaseH
Molecular Weight
65223.615 Da
References
  1. van Leeuwen R, Lange JM, Hussey EK, Donn KH, Hall ST, Harker AJ, Jonker P, Danner SA: The safety and pharmacokinetics of a reverse transcriptase inhibitor, 3TC, in patients with HIV infection: a phase I study. AIDS. 1992 Dec;6(12):1471-5. [PubMed:1283519]
Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Adduct
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Pan XP, Li LJ, Du WB, Li MW, Cao HC, Sheng JF: Differences of YMDD mutational patterns, precore/core promoter mutations, serum HBV DNA levels in lamivudine-resistant hepatitis B genotypes B and C. J Viral Hepat. 2007 Nov;14(11):767-74. [PubMed:17927612]
  4. Dai CY, Yu ML, Hsieh MY, Lee LP, Hou NJ, Huang JF, Chen SC, Lin ZY, Hsieh MY, Wang LY, Tsai JF, Chang WY, Chuang WL: Early response to lamivudine therapy in clinically non-cirrhotic chronic hepatitis B patients with decompensation. Liver Int. 2007 Dec;27(10):1364-70. Epub 2007 Sep 26. [PubMed:17900250]
  5. Ma H, Guo F, Wei L, Sun Y, Wang H: [The prospective study of the clinical features and outcome of HBeAg-negative and HBeAg-positive cirrhosis in patients with chronic type B hepatitis]. Zhonghua Yi Xue Za Zhi. 2007 Jul 10;87(26):1832-5. [PubMed:17922993]
Kind
Protein
Organism
HBV-F
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Multifunctional enzyme that converts the viral RNA genome into dsDNA in viral cytoplasmic capsids. This enzyme displays a DNA polymerase activity that can copy either DNA or RNA templates, and a ri...
Gene Name
P
Uniprot ID
Q05486
Uniprot Name
Protein P
Molecular Weight
94257.43 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Stuyver LJ, Locarnini SA, Lok A, Richman DD, Carman WF, Dienstag JL, Schinazi RF: Nomenclature for antiviral-resistant human hepatitis B virus mutations in the polymerase region. Hepatology. 2001 Mar;33(3):751-7. [PubMed:11230757]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based...
Gene Name
DCK
Uniprot ID
P27707
Uniprot Name
Deoxycytidine kinase
Molecular Weight
30518.315 Da
References
  1. Hunsucker SA, Mitchell BS, Spychala J: The 5'-nucleotidases as regulators of nucleotide and drug metabolism. Pharmacol Ther. 2005 Jul;107(1):1-30. [PubMed:15963349]
  2. Cihlar T, Ray AS: Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010 Jan;85(1):39-58. doi: 10.1016/j.antiviral.2009.09.014. Epub 2009 Nov 1. [PubMed:19887088]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Uridylate kinase activity
Specific Function
Catalyzes the phosphorylation of pyrimidine nucleoside monophosphates at the expense of ATP. Plays an important role in de novo pyrimidine nucleotide biosynthesis. Has preference for UMP and CMP as...
Gene Name
CMPK1
Uniprot ID
P30085
Uniprot Name
UMP-CMP kinase
Molecular Weight
22222.175 Da
References
  1. Hunsucker SA, Mitchell BS, Spychala J: The 5'-nucleotidases as regulators of nucleotide and drug metabolism. Pharmacol Ther. 2005 Jul;107(1):1-30. [PubMed:15963349]
  2. Cihlar T, Ray AS: Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010 Jan;85(1):39-58. doi: 10.1016/j.antiviral.2009.09.014. Epub 2009 Nov 1. [PubMed:19887088]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Phosphoglycerate kinase activity
Specific Function
In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein).
Gene Name
PGK1
Uniprot ID
P00558
Uniprot Name
Phosphoglycerate kinase 1
Molecular Weight
44614.36 Da
References
  1. Hunsucker SA, Mitchell BS, Spychala J: The 5'-nucleotidases as regulators of nucleotide and drug metabolism. Pharmacol Ther. 2005 Jul;107(1):1-30. [PubMed:15963349]
  2. Cihlar T, Ray AS: Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010 Jan;85(1):39-58. doi: 10.1016/j.antiviral.2009.09.014. Epub 2009 Nov 1. [PubMed:19887088]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Ribosomal small subunit binding
Specific Function
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-sit...
Gene Name
NME1
Uniprot ID
P15531
Uniprot Name
Nucleoside diphosphate kinase A
Molecular Weight
17148.635 Da
References
  1. Hunsucker SA, Mitchell BS, Spychala J: The 5'-nucleotidases as regulators of nucleotide and drug metabolism. Pharmacol Ther. 2005 Jul;107(1):1-30. [PubMed:15963349]
  2. Cihlar T, Ray AS: Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010 Jan;85(1):39-58. doi: 10.1016/j.antiviral.2009.09.014. Epub 2009 Nov 1. [PubMed:19887088]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Major role in the synthesis of nucleoside triphosphates other than ATP. Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds ...
Gene Name
NME2
Uniprot ID
P22392
Uniprot Name
Nucleoside diphosphate kinase B
Molecular Weight
17297.935 Da
References
  1. Hunsucker SA, Mitchell BS, Spychala J: The 5'-nucleotidases as regulators of nucleotide and drug metabolism. Pharmacol Ther. 2005 Jul;107(1):1-30. [PubMed:15963349]
  2. Cihlar T, Ray AS: Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010 Jan;85(1):39-58. doi: 10.1016/j.antiviral.2009.09.014. Epub 2009 Nov 1. [PubMed:19887088]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Lipid binding
Specific Function
Controls phosphatidylcholine synthesis.
Gene Name
PCYT1A
Uniprot ID
P49585
Uniprot Name
Choline-phosphate cytidylyltransferase A
Molecular Weight
41730.67 Da
References
  1. Zhou Z, Rodman JH, Flynn PM, Robbins BL, Wilcox CK, D'Argenio DZ: Model for intracellular Lamivudine metabolism in peripheral blood mononuclear cells ex vivo and in human immunodeficiency virus type 1-infected adolescents. Antimicrob Agents Chemother. 2006 Aug;50(8):2686-94. [PubMed:16870759]
  2. KENNEDY EP, BORKENHAGEN LF, SMITH SW: Possible metabolic functions of deoxycytidine diphosphate choline and deoxycytidine diphosphate ethanolamine. J Biol Chem. 1959 Aug;234(8):1998-2000. [PubMed:13673002]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Ethanolamine-phosphate cytidylyltransferase activity
Specific Function
Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine.
Gene Name
PCYT2
Uniprot ID
Q99447
Uniprot Name
Ethanolamine-phosphate cytidylyltransferase
Molecular Weight
43835.23 Da
References
  1. Zhou Z, Rodman JH, Flynn PM, Robbins BL, Wilcox CK, D'Argenio DZ: Model for intracellular Lamivudine metabolism in peripheral blood mononuclear cells ex vivo and in human immunodeficiency virus type 1-infected adolescents. Antimicrob Agents Chemother. 2006 Aug;50(8):2686-94. [PubMed:16870759]
  2. KENNEDY EP, BORKENHAGEN LF, SMITH SW: Possible metabolic functions of deoxycytidine diphosphate choline and deoxycytidine diphosphate ethanolamine. J Biol Chem. 1959 Aug;234(8):1998-2000. [PubMed:13673002]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Pyrimidine nucleotide binding
Specific Function
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name
NT5C
Uniprot ID
Q8TCD5
Uniprot Name
5'(3')-deoxyribonucleotidase, cytosolic type
Molecular Weight
23382.54 Da
References
  1. Hunsucker SA, Mitchell BS, Spychala J: The 5'-nucleotidases as regulators of nucleotide and drug metabolism. Pharmacol Ther. 2005 Jul;107(1):1-30. [PubMed:15963349]
  2. Cihlar T, Ray AS: Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine. Antiviral Res. 2010 Jan;85(1):39-58. doi: 10.1016/j.antiviral.2009.09.014. Epub 2009 Nov 1. [PubMed:19887088]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. [PubMed:15814459]
  2. Bocedi A, Notari S, Menegatti E, Fanali G, Fasano M, Ascenzi P: Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. FEBS J. 2005 Dec;272(24):6287-96. [PubMed:16336266]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Olson DP, Scadden DT, D'Aquila RT, De Pasquale MP: The protease inhibitor ritonavir inhibits the functional activity of the multidrug resistance related-protein 1 (MRP-1). AIDS. 2002 Sep 6;16(13):1743-7. [PubMed:12218384]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Wang X, Furukawa T, Nitanda T, Okamoto M, Sugimoto Y, Akiyama S, Baba M: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Mol Pharmacol. 2003 Jan;63(1):65-72. [PubMed:12488537]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Arimany-Nardi C, Minuesa G, Keller T, Erkizia I, Koepsell H, Martinez-Picado J, Pastor-Anglada M: Role of Human Organic Cation Transporter 1 (hOCT1) Polymorphisms in Lamivudine (3TC) Uptake and Drug-Drug Interactions. Front Pharmacol. 2016 Jun 24;7:175. doi: 10.3389/fphar.2016.00175. eCollection 2016. [PubMed:27445813]
  2. Choi MK, Song IS: Genetic variants of organic cation transporter 1 (OCT1) and OCT2 significantly reduce lamivudine uptake. Biopharm Drug Dispos. 2012 Apr;33(3):170-8. doi: 10.1002/bdd.1783. Epub 2012 Mar 17. [PubMed:22415520]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Minuesa G, Volk C, Molina-Arcas M, Gorboulev V, Erkizia I, Arndt P, Clotet B, Pastor-Anglada M, Koepsell H, Martinez-Picado J: Transport of lamivudine [(-)-beta-L-2',3'-dideoxy-3'-thiacytidine] and high-affinity interaction of nucleoside reverse transcriptase inhibitors with human organic cation transporters 1, 2, and 3. J Pharmacol Exp Ther. 2009 Apr;329(1):252-61. doi: 10.1124/jpet.108.146225. Epub 2009 Jan 13. [PubMed:19141712]
  2. Errasti-Murugarren E, Pastor-Anglada M: Drug transporter pharmacogenetics in nucleoside-based therapies. Pharmacogenomics. 2010 Jun;11(6):809-41. doi: 10.2217/pgs.10.70. [PubMed:20504255]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Minuesa G, Volk C, Molina-Arcas M, Gorboulev V, Erkizia I, Arndt P, Clotet B, Pastor-Anglada M, Koepsell H, Martinez-Picado J: Transport of lamivudine [(-)-beta-L-2',3'-dideoxy-3'-thiacytidine] and high-affinity interaction of nucleoside reverse transcriptase inhibitors with human organic cation transporters 1, 2, and 3. J Pharmacol Exp Ther. 2009 Apr;329(1):252-61. doi: 10.1124/jpet.108.146225. Epub 2009 Jan 13. [PubMed:19141712]
  2. Errasti-Murugarren E, Pastor-Anglada M: Drug transporter pharmacogenetics in nucleoside-based therapies. Pharmacogenomics. 2010 Jun;11(6):809-41. doi: 10.2217/pgs.10.70. [PubMed:20504255]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Errasti-Murugarren E, Pastor-Anglada M: Drug transporter pharmacogenetics in nucleoside-based therapies. Pharmacogenomics. 2010 Jun;11(6):809-41. doi: 10.2217/pgs.10.70. [PubMed:20504255]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Errasti-Murugarren E, Pastor-Anglada M: Drug transporter pharmacogenetics in nucleoside-based therapies. Pharmacogenomics. 2010 Jun;11(6):809-41. doi: 10.2217/pgs.10.70. [PubMed:20504255]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name
ABCC3
Uniprot ID
O15438
Uniprot Name
Canalicular multispecific organic anion transporter 2
Molecular Weight
169341.14 Da
References
  1. Errasti-Murugarren E, Pastor-Anglada M: Drug transporter pharmacogenetics in nucleoside-based therapies. Pharmacogenomics. 2010 Jun;11(6):809-41. doi: 10.2217/pgs.10.70. [PubMed:20504255]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Errasti-Murugarren E, Pastor-Anglada M: Drug transporter pharmacogenetics in nucleoside-based therapies. Pharmacogenomics. 2010 Jun;11(6):809-41. doi: 10.2217/pgs.10.70. [PubMed:20504255]

Drug created on June 13, 2005 07:24 / Updated on October 27, 2020 11:12

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