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Identification
NameLamivudine
Accession NumberDB00709  (APRD00681)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionA 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).
Structure
Thumb
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
Epivir
Lamivudin
Lamivudina
Lamivudine
Lamivudinum
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
3-TCNot AvailableNot AvailableNot applicableDetails
GR 109714 XNot AvailableNot AvailableNot applicableDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
3tcTablet150 mgOralViiv Healthcare Ulc1995-12-31Not applicableCanada
3tcSolution10 mgOralViiv Healthcare Ulc1995-12-31Not applicableCanada
3tcTablet300 mgOralViiv Healthcare Ulc2003-09-09Not applicableCanada
Auro-lamivudineTablet150 mgOralAuro Pharma Inc2013-10-16Not applicableCanada
Auro-lamivudineTablet300 mgOralAuro Pharma Inc2013-10-16Not applicableCanada
EpivirTablet, film coated300 mg/1OralViiv Healthcare Ulc2010-10-04Not applicableUs
EpivirTablet, film coated150 mg/1OralRebel Distributors1995-11-21Not applicableUs
EpivirTablet, film coated150 mg/1OralPhysicians Total Care, Inc.1995-12-01Not applicableUs
EpivirTablet, film coated150 mgOralViiv Healthcare Ulc1996-08-08Not applicableEu
EpivirSolution10 mg/mLOralViiv Healthcare Ulc2010-10-04Not applicableUs
EpivirTablet, film coated150 mg/1OralRemedy Repack2013-03-152016-10-13Us
EpivirTablet, film coated300 mg/1OralPhysicians Total Care, Inc.2007-09-28Not applicableUs
EpivirTablet, film coated300 mgOralViiv Healthcare Ulc1996-08-08Not applicableEu
EpivirTablet300 mg/1OralRemedy Repack2011-04-202017-11-16Us
EpivirTablet, film coated150 mg/1OralRemedy Repack2011-07-132016-12-07Us
EpivirTablet, film coated150 mg/1OralA S Medication Solutions2010-10-04Not applicableUs
EpivirTablet, film coated150 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
EpivirTablet, film coated150 mgOralViiv Healthcare Ulc1996-08-08Not applicableEu
EpivirTablet, film coated300 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
EpivirSolution10 mg/mlOralViiv Healthcare Ulc1996-08-08Not applicableEu
EpivirTablet, film coated150 mg/1OralViiv Healthcare Ulc2010-10-04Not applicableUs
EpivirTablet, film coated150 mg/1OralKaiser Foundations Hospitals2011-03-15Not applicableUs
EpivirTablet, film coated300 mgOralViiv Healthcare Ulc1996-08-08Not applicableEu
Epivir HbvTablet, film coated100 mg/1OralGlaxosmithkline Inc1998-12-17Not applicableUs
Epivir HbvSolution5 mg/mLOralGlaxosmithkline Inc1998-12-23Not applicableUs
Epivir HbvTablet, film coated100 mg/1OralState of Florida DOH Central Pharmacy2014-01-01Not applicableUs
HeptovirTablet100 mgOralGlaxosmithkline Inc1998-12-02Not applicableCanada
HeptovirSolution5 mgOralGlaxosmithkline Inc1999-03-30Not applicableCanada
LamivudineTablet, film coated100 mg/1OralPrasco, Laboratories2014-09-05Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-lamivudineTablet150 mgOralApotex Corporation2012-05-18Not applicableCanada
Apo-lamivudineTablet300 mgOralApotex Corporation2012-05-18Not applicableCanada
Apo-lamivudine HbvTablet100 mgOralApotex Corporation2012-09-21Not applicableCanada
LamivudineSolution10 mg/mLOralMarlex Pharmaceuticals Inc2016-02-01Not applicableUs
LamivudineTablet, film coated150 mg/1OralApotex Corporation2011-12-02Not applicableUs
LamivudineTablet, film coated150 mg/1OralAvera Mc Kennan Hospital2016-06-02Not applicableUs
LamivudineTablet, film coated300 mg/1OralAv Pak2015-07-30Not applicableUs
LamivudineTablet, film coated100 mg/1OralApotex Corporation2014-01-03Not applicableUs
LamivudineTablet, film coated150 mg/1OralRemedy Repack2015-05-302017-04-14Us
LamivudineTablet, film coated150 mg/1OralMylan Pharmaceuticals2016-03-28Not applicableUs
LamivudineTablet, film coated300 mg/1OralMylan Pharmaceuticals2016-03-28Not applicableUs
LamivudineTablet, film coated300 mg/1OralApotex Corporation2011-12-02Not applicableUs
LamivudineTablet, film coated300 mg/1OralRemedy Repack2013-03-282016-10-13Us
LamivudineTablet, film coated150 mg/1Oralbryant ranch prepack2011-11-17Not applicableUs
LamivudineTablet, film coated150 mg/1OralRemedy Repack2017-04-19Not applicableUs
LamivudineTablet, film coated150 mg/1OralAurobindo Pharma2011-11-17Not applicableUs
LamivudineTablet, film coated150 mg/1OralRemedy Repack2012-01-202016-10-26Us
LamivudineSolution10 mg/mLOralSilarx Pharmaceuticals, Inc.2014-01-30Not applicableUs
LamivudineTablet150 mg/1OralAppco Pharma Llc2017-02-01Not applicableUs
LamivudineTablet, film coated100 mg/1OralKaiser Foundations Hospitals2014-05-29Not applicableUs
LamivudineTablet, film coated150 mg/1OralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
LamivudineTablet150 mg/1OralIngenus Pharmaceuticals Llc2017-02-01Not applicableUs
LamivudineTablet, film coated300 mg/1OralAurobindo Pharma2011-11-17Not applicableUs
LamivudineTablet, film coated150 mg/1OralAmerincan Health Packaging2012-02-01Not applicableUs
LamivudineTablet, film coated150 mg/1OralAurobindo Pharma2016-11-21Not applicableUs
LamivudineTablet300 mg/1OralAppco Pharma Llc2017-02-01Not applicableUs
LamivudineTablet, film coated100 mg/1OralKaiser Foundations Hospitals2015-03-20Not applicableUs
LamivudineTablet, film coated300 mg/1OralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
LamivudineTablet300 mg/1OralIngenus Pharmaceuticals Llc2017-02-01Not applicableUs
LamivudineTablet, film coated100 mg/1OralMylan Pharmaceuticals2015-01-09Not applicableUs
LamivudineTablet, film coated150 mg/1OralLupin Pharmaceuticals2015-03-25Not applicableUs
LamivudineTablet, film coated300 mg/1OralAurobindo Pharma2016-11-21Not applicableUs
LamivudineSolution10 mg/mLOralCitron Pharma LLC2016-11-21Not applicableUs
LamivudineTablet, film coated100 mg/1OralCamber Pharmaceuticals2014-01-02Not applicableUs
LamivudineTablet, film coated150 mg/1OralGolden State Medical Supply2011-12-02Not applicableUs
LamivudineTablet, film coated150 mg/1OralCamber Pharmaceuticals2014-01-06Not applicableUs
LamivudineTablet, film coated300 mg/1OralLupin Pharmaceuticals2015-03-25Not applicableUs
LamivudineSolution10 mg/mLOralAurobindo Pharma2016-11-21Not applicableUs
LamivudineTablet, film coated150 mg/1OralMajor2011-12-02Not applicableUs
LamivudineTablet, film coated150 mg/1OralAv Pak2015-07-30Not applicableUs
LamivudineTablet, film coated300 mg/1OralGolden State Medical Supply2011-12-02Not applicableUs
LamivudineTablet, film coated300 mg/1OralCamber Pharmaceuticals2014-01-06Not applicableUs
LamivudineTablet, film coated300 mg/1OralRemedy Repack2016-01-19Not applicableUs
Lamivudine and ZidovudineTablet, film coated150 mg/1OralRemedy Repack2013-04-112016-10-13Us
Lamivudine TevaTablet, film coated100 mgOralTeva B.V.  2009-10-23Not applicableEu
Lamivudine TevaTablet, film coated100 mgOralTeva B.V.  2009-10-23Not applicableEu
Lamivudine TevaTablet, film coated100 mgOralTeva B.V.  2009-10-23Not applicableEu
Lamivudine TevaTablet, film coated100 mgOralTeva B.V.  2009-10-23Not applicableEu
Lamivudine TevaTablet, film coated100 mgOralTeva B.V.  2009-10-23Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated150 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated300 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated150 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated300 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated300 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated150 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated300 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated300 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated150 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated300 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated150 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated300 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated150 mgOralTeva B.V.  2009-12-10Not applicableEu
Lamivudine Teva Pharma B.V.Tablet, film coated150 mgOralTeva B.V.  2009-12-10Not applicableEu
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AmilitrapDosa
AntihebMebiphar
AvilamBeximco
AvolamRanbaxy Laboratories
Epivir-HBVGlaxoSmithKline
FlamivudFlamingo Pharmacueticals
GanvirelIvax
HepavirSquare
HepitecGlaxoSmithKline
HeptavirHetero
HeptodinGlaxoSmithKline
HeptodineGlaxoSmithKline
LamdaCadila
LamibergenPaylos
LamidacZydus
LamitecZifam India
LamivirIncepta
ZeffixGlaxoSmithKline
Brand mixtures
NameLabellerIngredients
Abacavir and LamivudineTeva
Abacavir Sulfate, Lamivudine and ZidovudineLupin Pharmaceuticals
Apo-abacavir-lamivudineApotex Corporation
Apo-abacavir-lamivudine-zidovudineApotex Corporation
Apo-lamivudine-zidovudineApotex Corporation
Apo-zidovudine-lamivudine-nevirapineApotex Corporation
Auro-abacavir/lamivudineAuro Pharma Inc
Auro-lamivudine/zidovudineAuro Pharma Inc
CombivirStat Rx USA
DutrebisMerck Sharp & Dohme Limited  
EpzicomRemedy Repack
KivexaViiv Healthcare Ulc
Lamivudine and ZidovudineRebel Distributors
Lamivudine ZidovudineDirectrx
Mylan-abacavir/lamivudineMylan Pharmaceuticals
PMS-abacavir-lamivudinePharmascience Inc
Teva-abacavir/lamivudineTeva
Teva-lamivudine/zidovudineTeva
TriumeqViiv Healthcare Ulc
TrizivirState of Florida DOH Central Pharmacy
Categories
UNII2T8Q726O95
CAS number134678-17-4
WeightAverage: 229.256
Monoisotopic: 229.052111923
Chemical FormulaC8H11N3O3S
InChI KeyJTEGQNOMFQHVDC-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)[C@@H]1CS[[email protected]](CO)O1
Pharmacology
IndicationFor the treatment of HIV infection and chronic hepatitis B (HBV).
Structured Indications
PharmacodynamicsLamivudine 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.
Mechanism of actionLamivudine 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Reverse transcriptase/RNaseHProteinyes
inhibitor
Human immunodeficiency virus 1Q72547 details
DNANucleotideyes
adduct
Humannot applicabledetails
Protein PProteinyes
inhibitor
HBV-FQ05486 details
Related Articles
AbsorptionLamivudine 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.

SubstrateEnzymesProduct
Lamivudine
Lamivudine sulfoxideDetails
Lamivudine
Lamivudine-diphosphate-cholineDetails
Lamivudine
Not Available
Lamivudine-diphosphate-ethanolamineDetails
Lamivudine
Not Available
Lamivudine-monophosphateDetails
Lamivudine
Not Available
Lamivudine-triphosphateDetails
Route of eliminationThe 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 life5 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]
ToxicityThe 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
PathwayCategorySMPDB ID
Lamivudine Metabolism PathwayDrug metabolismSMP00649
Lamivudine Action PathwayDrug actionSMP00742
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetaminophenThe serum concentration of Lamivudine can be increased when it is combined with Acetaminophen.Approved
AfatinibThe serum concentration of Lamivudine can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Lamivudine can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Lamivudine can be decreased when it is combined with Aldosterone.Experimental
AlectinibThe serum concentration of Lamivudine can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Lamivudine can be increased when it is combined with Alfentanil.Approved, Illicit
AmantadineThe serum concentration of Lamivudine can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Lamivudine can be increased when it is combined with Aminohippuric acid.Approved
AmiodaroneThe serum concentration of Lamivudine can be decreased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Lamivudine can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Lamivudine can be increased when it is combined with Amlodipine.Approved
AmprenavirThe serum concentration of Lamivudine can be decreased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Lamivudine can be increased when it is combined with Amsacrine.Approved
AstemizoleThe serum concentration of Lamivudine can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe serum concentration of Lamivudine can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Lamivudine can be increased when it is combined with Atenolol.Approved
AtorvastatinThe serum concentration of Lamivudine can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Lamivudine can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Lamivudine can be increased when it is combined with Azithromycin.Approved
BenzocaineThe serum concentration of Lamivudine can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Lamivudine can be increased when it is combined with Bepridil.Approved, Withdrawn
BiperidenThe serum concentration of Lamivudine can be increased when it is combined with Biperiden.Approved
BosutinibThe serum concentration of Lamivudine can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Lamivudine can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Lamivudine can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BupropionThe serum concentration of Lamivudine can be increased when it is combined with Bupropion.Approved
BuspironeThe serum concentration of Lamivudine can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe serum concentration of Lamivudine can be increased when it is combined with Cabazitaxel.Approved
CaffeineThe serum concentration of Lamivudine can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Lamivudine can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Lamivudine can be increased when it is combined with Candesartan.Approved
CaptoprilThe serum concentration of Lamivudine can be increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Lamivudine can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Lamivudine can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Lamivudine can be increased when it is combined with Caspofungin.Approved
ChloroquineThe serum concentration of Lamivudine can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Lamivudine can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Lamivudine can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Lamivudine can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
CholesterolThe serum concentration of Lamivudine can be increased when it is combined with Cholesterol.Experimental
Cholic AcidThe serum concentration of Lamivudine can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Lamivudine can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Lamivudine can be decreased when it is combined with Cimetidine.Approved
CiprofloxacinThe serum concentration of Lamivudine can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Lamivudine can be increased when it is combined with Citalopram.Approved
ClarithromycinThe serum concentration of Lamivudine can be increased when it is combined with Clarithromycin.Approved
ClofazimineThe serum concentration of Lamivudine can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineThe serum concentration of Lamivudine can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe serum concentration of Lamivudine can be decreased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Lamivudine can be increased when it is combined with Cobicistat.Approved
ColchicineThe serum concentration of Lamivudine can be increased when it is combined with Colchicine.Approved
ColforsinThe serum concentration of Lamivudine can be increased when it is combined with Colforsin.Experimental
CrizotinibThe serum concentration of Lamivudine can be increased when it is combined with Crizotinib.Approved
CyclophosphamideThe serum concentration of Lamivudine can be increased when it is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Lamivudine can be decreased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DaclatasvirThe serum concentration of Lamivudine can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Lamivudine can be increased when it is combined with Dactinomycin.Approved
DasatinibThe serum concentration of Lamivudine can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Lamivudine can be decreased when it is combined with Daunorubicin.Approved
DesipramineThe serum concentration of Lamivudine can be increased when it is combined with Desipramine.Approved
DesloratadineThe serum concentration of Lamivudine can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Lamivudine can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Lamivudine can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Lamivudine can be increased when it is combined with Diclofenac.Approved, Vet Approved
DigoxinThe serum concentration of Lamivudine can be decreased when it is combined with Digoxin.Approved
DihydroergotamineThe serum concentration of Lamivudine can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Lamivudine can be increased when it is combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Lamivudine can be increased when it is combined with Dipyridamole.Approved
DoxazosinThe serum concentration of Lamivudine can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Lamivudine can be increased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Lamivudine can be decreased when it is combined with Doxorubicin.Approved, Investigational
DronabinolThe serum concentration of Lamivudine can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe serum concentration of Lamivudine can be increased when it is combined with Dronedarone.Approved
ElbasvirThe serum concentration of Lamivudine can be increased when it is combined with Elbasvir.Approved
EltrombopagThe serum concentration of Lamivudine can be increased when it is combined with Eltrombopag.Approved
EmtricitabineThe risk or severity of adverse effects can be increased when Lamivudine is combined with Emtricitabine.Approved, Investigational
EnalaprilThe serum concentration of Lamivudine can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Lamivudine can be increased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Lamivudine can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Lamivudine can be increased when it is combined with Ergotamine.Approved
ErythromycinThe serum concentration of Lamivudine can be decreased when it is combined with Erythromycin.Approved, Vet Approved
EstramustineThe serum concentration of Lamivudine can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Lamivudine can be decreased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of Lamivudine can be decreased when it is combined with Estrone.Approved
EtoposideThe serum concentration of Lamivudine can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Lamivudine can be increased when it is combined with Etravirine.Approved
FelodipineThe serum concentration of Lamivudine can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Lamivudine can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Lamivudine can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Lamivudine can be increased when it is combined with Fidaxomicin.Approved
FluconazoleThe serum concentration of Lamivudine can be increased when it is combined with Fluconazole.Approved
FluoxetineThe serum concentration of Lamivudine can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Lamivudine can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Lamivudine can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Lamivudine can be increased when it is combined with Flurazepam.Approved, Illicit
FluvoxamineThe serum concentration of Lamivudine can be increased when it is combined with Fluvoxamine.Approved, Investigational
GanciclovirThe risk or severity of adverse effects can be increased when Ganciclovir is combined with Lamivudine.Approved, Investigational
GefitinibThe serum concentration of Lamivudine can be increased when it is combined with Gefitinib.Approved, Investigational
GenisteinThe serum concentration of Lamivudine can be increased when it is combined with Genistein.Investigational
GlyburideThe serum concentration of Lamivudine can be increased when it is combined with Glyburide.Approved
GlycerolThe serum concentration of Lamivudine can be increased when it is combined with Glycerol.Experimental
Gramicidin DThe serum concentration of Lamivudine can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Lamivudine can be increased when it is combined with Grepafloxacin.Withdrawn
HaloperidolThe serum concentration of Lamivudine can be increased when it is combined with Haloperidol.Approved
HydrocortisoneThe serum concentration of Lamivudine can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe serum concentration of Lamivudine can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Lamivudine can be increased when it is combined with Imatinib.Approved
ImipramineThe serum concentration of Lamivudine can be increased when it is combined with Imipramine.Approved
IndinavirThe serum concentration of Lamivudine can be decreased when it is combined with Indinavir.Approved
IndomethacinThe serum concentration of Lamivudine can be increased when it is combined with Indomethacin.Approved, Investigational
IsavuconazoniumThe serum concentration of Lamivudine can be increased when it is combined with Isavuconazonium.Approved, Investigational
ItraconazoleThe serum concentration of Lamivudine can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Lamivudine can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Lamivudine can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Lamivudine can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe serum concentration of Lamivudine can be increased when it is combined with Ketoconazole.Approved, Investigational
LansoprazoleThe serum concentration of Lamivudine can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Lamivudine can be increased when it is combined with Lapatinib.Approved, Investigational
LevofloxacinThe serum concentration of Lamivudine can be increased when it is combined with Levofloxacin.Approved, Investigational
LevothyroxineThe serum concentration of Lamivudine can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Lamivudine can be increased when it is combined with Lidocaine.Approved, Vet Approved
LiothyronineThe serum concentration of Lamivudine can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Lamivudine can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Lamivudine can be increased when it is combined with Lisinopril.Approved, Investigational
LomitapideThe serum concentration of Lamivudine can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Lamivudine can be increased when it is combined with Loperamide.Approved
LopinavirThe serum concentration of Lamivudine can be increased when it is combined with Lopinavir.Approved
LoratadineThe serum concentration of Lamivudine can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Lamivudine can be increased when it is combined with Losartan.Approved
LovastatinThe serum concentration of Lamivudine can be increased when it is combined with Lovastatin.Approved, Investigational
LumacaftorThe serum concentration of Lamivudine can be decreased when it is combined with Lumacaftor.Approved
MaprotilineThe serum concentration of Lamivudine can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Lamivudine can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Lamivudine can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Lamivudine can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Lamivudine can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneThe serum concentration of Lamivudine can be increased when it is combined with Methadone.Approved
MetoprololThe serum concentration of Lamivudine can be increased when it is combined with Metoprolol.Approved, Investigational
MibefradilThe serum concentration of Lamivudine can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Lamivudine can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Lamivudine can be decreased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Lamivudine can be decreased when it is combined with Mifepristone.Approved, Investigational
MitomycinThe serum concentration of Lamivudine can be increased when it is combined with Mitomycin.Approved
MitoxantroneThe serum concentration of Lamivudine can be decreased when it is combined with Mitoxantrone.Approved, Investigational
MorphineThe serum concentration of Lamivudine can be increased when it is combined with Morphine.Approved, Investigational
NaltrexoneThe serum concentration of Lamivudine can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Lamivudine can be increased when it is combined with Naringenin.Experimental
NefazodoneThe serum concentration of Lamivudine can be decreased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Lamivudine can be decreased when it is combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Lamivudine can be increased when it is combined with Neostigmine.Approved, Vet Approved
NicardipineThe serum concentration of Lamivudine can be increased when it is combined with Nicardipine.Approved
NifedipineThe serum concentration of Lamivudine can be decreased when it is combined with Nifedipine.Approved
NilotinibThe serum concentration of Lamivudine can be increased when it is combined with Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Lamivudine can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Lamivudine can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Lamivudine can be increased when it is combined with Nitrendipine.Approved
NorethisteroneThe serum concentration of Lamivudine can be decreased when it is combined with Norethisterone.Approved
OmeprazoleThe serum concentration of Lamivudine can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
P-NitrophenolThe serum concentration of Lamivudine can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe serum concentration of Lamivudine can be increased when it is combined with Paclitaxel.Approved, Vet Approved
Palmitic AcidThe serum concentration of Lamivudine can be increased when it is combined with Palmitic Acid.Experimental
PantoprazoleThe serum concentration of Lamivudine can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Lamivudine can be increased when it is combined with Paroxetine.Approved, Investigational
PerindoprilThe serum concentration of Lamivudine can be increased when it is combined with Perindopril.Approved
PhenobarbitalThe serum concentration of Lamivudine can be decreased when it is combined with Phenobarbital.Approved
PimozideThe serum concentration of Lamivudine can be increased when it is combined with Pimozide.Approved
Platelet Activating FactorThe serum concentration of Lamivudine can be decreased when it is combined with Platelet Activating Factor.Experimental
PonatinibThe serum concentration of Lamivudine can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe serum concentration of Lamivudine can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Lamivudine can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Lamivudine can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Lamivudine can be increased when it is combined with Prednisone.Approved, Vet Approved
ProbenecidThe serum concentration of Lamivudine can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Lamivudine can be decreased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Lamivudine can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Lamivudine can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Lamivudine can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Lamivudine can be increased when it is combined with Protriptyline.Approved
QuercetinThe serum concentration of Lamivudine can be increased when it is combined with Quercetin.Experimental
QuinacrineThe serum concentration of Lamivudine can be increased when it is combined with Quinacrine.Approved
QuinidineThe serum concentration of Lamivudine can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Lamivudine can be increased when it is combined with Quinine.Approved
RanitidineThe serum concentration of Lamivudine can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Lamivudine can be increased when it is combined with Ranolazine.Approved, Investigational
ReboxetineThe serum concentration of Lamivudine can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Lamivudine can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Lamivudine can be decreased when it is combined with Reserpine.Approved
RibavirinRibavirin may increase the hepatotoxic activities of Lamivudine.Approved
RifampicinThe serum concentration of Lamivudine can be decreased when it is combined with Rifampicin.Approved
RilpivirineThe serum concentration of Lamivudine can be increased when it is combined with Rilpivirine.Approved
RitonavirThe serum concentration of Lamivudine can be decreased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Lamivudine can be increased when it is combined with Rolapitant.Approved
SaquinavirThe serum concentration of Lamivudine can be decreased when it is combined with Saquinavir.Approved, Investigational
ScopolamineThe serum concentration of Lamivudine can be increased when it is combined with Scopolamine.Approved
SelegilineThe serum concentration of Lamivudine can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Lamivudine can be increased when it is combined with Sertraline.Approved
SimeprevirThe serum concentration of Lamivudine can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Lamivudine can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Lamivudine can be decreased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Lamivudine can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Lamivudine can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Lamivudine can be decreased when it is combined with St. John&#39;s Wort.Nutraceutical
StaurosporineThe serum concentration of Lamivudine can be increased when it is combined with Staurosporine.Experimental
StreptozocinThe serum concentration of Lamivudine can be decreased when it is combined with Streptozocin.Approved
SulfinpyrazoneThe serum concentration of Lamivudine can be increased when it is combined with Sulfinpyrazone.Approved
SumatriptanThe serum concentration of Lamivudine can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Lamivudine can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Lamivudine can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Lamivudine can be decreased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Lamivudine can be decreased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Lamivudine can be increased when it is combined with Taurocholic Acid.Experimental
TelmisartanThe serum concentration of Lamivudine can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Lamivudine can be increased when it is combined with Temsirolimus.Approved
TerazosinThe serum concentration of Lamivudine can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Lamivudine can be increased when it is combined with Terfenadine.Withdrawn
TeriflunomideThe serum concentration of Lamivudine can be increased when it is combined with Teriflunomide.Approved
TesmilifeneThe serum concentration of Lamivudine can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Lamivudine can be increased when it is combined with Testosterone.Approved, Investigational
TicagrelorThe serum concentration of Lamivudine can be increased when it is combined with Ticagrelor.Approved
TolvaptanThe serum concentration of Lamivudine can be increased when it is combined with Tolvaptan.Approved
TrazodoneThe serum concentration of Lamivudine can be decreased when it is combined with Trazodone.Approved, Investigational
TrifluoperazineThe serum concentration of Lamivudine can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Lamivudine can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimTrimethoprim may decrease the excretion rate of Lamivudine which could result in a higher serum level.Approved, Vet Approved
TrimipramineThe serum concentration of Lamivudine can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Lamivudine can be increased when it is combined with Troleandomycin.Approved
ValganciclovirThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Lamivudine.Approved, Investigational
VenlafaxineThe serum concentration of Lamivudine can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Lamivudine can be decreased when it is combined with Verapamil.Approved
VinblastineThe serum concentration of Lamivudine can be decreased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Lamivudine can be decreased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Lamivudine can be increased when it is combined with Vinorelbine.Approved, Investigational
ZimelidineThe serum concentration of Lamivudine can be increased when it is combined with Zimelidine.Withdrawn
Food Interactions
  • Take without regard to meals. Food does not decrease the extent of absorption, but it decreases the Cmax by slowing the rate of absorption.
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 ]
External Links
ATC CodesJ05AR02J05AR13J05AR12J05AR01J05AR05J05AR07J05AR04J05AR16J05AR11J05AF05
AHFS Codes
  • 08:18.08.20
PDB EntriesNot Available
FDA labelDownload (310 KB)
MSDSDownload (57.6 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Malaria1
1CompletedNot AvailableHIV Disease1
1CompletedNot AvailableHIV-DDI1
1CompletedNot AvailableInfection, Human Immunodeficiency Virus I1
1CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
1CompletedTreatmentAcquired Immunodeficiency Syndromes / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHIV Disease1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHepatitis B,Chronic1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections16
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pregnancy4
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
1Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1RecruitingTreatmentHIV Disease2
1Unknown StatusTreatmentAids / HIV Disease1
1, 2CompletedTreatmentHepatitis C / HIV Disease1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections5
1, 2RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1, 2Unknown StatusTreatmentLiver Cirrhosis1
1, 2WithdrawnPreventionLymphoma NOS1
2Active Not RecruitingTreatmentAcute HIV Infection / HIV CNS Involvement1
2Active Not RecruitingTreatmentHIV-1 Infections1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAcquired Immunodeficiency Syndromes / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAids / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentChronic Hepatitis B Infection1
2CompletedTreatmentChronic Hepatitis B Infection / Chronic Hepatitis D / Glomerulonephritis / Polyarteritis Nodosa1
2CompletedTreatmentHBV (Hepatitis B Virus) / Hepatitis / Hepatitis B1
2CompletedTreatmentHBV / Hepatitis B Virus (HBV)1
2CompletedTreatmentHIV-1 Infections4
2CompletedTreatmentHepatitis B1
2CompletedTreatmentHepatitis B,Chronic1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections40
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
2CompletedTreatmentLymphoma NOS1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2TerminatedTreatmentHIV-1 Infections2
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
2Unknown StatusPreventionHepatitis B / HIV Disease1
2Unknown StatusPreventionHIV Transmission / Human Immunodeficiency Virus (HIV) Infections1
2Unknown StatusPreventionHepatitis B Reactivation / Non-Hodgkin's Lymphoma (NHL)1
2Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentHIV Disease1
2, 3CompletedTreatmentHTLV-I-Associated Myelopathy1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2, 3CompletedTreatmentKaposi's Sarcoma AIDS Related1
2, 3CompletedTreatmentPrimary Biliary Cirrhosis (PBC)1
2, 3RecruitingTreatmentHIV Disease / Pediatric AIDS1
2, 3RecruitingTreatmentHepatocellular Carcinomas1
2, 3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3Unknown StatusNot AvailableLymphoma NOS1
3Active Not RecruitingNot AvailableHepatocellular Carcinomas1
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHIV-1 Infections6
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
3CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionAcquired Immunodeficiency Syndromes1
3CompletedPreventionDisease Transmission, Vertical / Human Immunodeficiency Virus (HIV) Infections / Vertical Human Immunodeficiency Virus Transmission1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections4
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Malaria1
3CompletedTreatmentAIDS-Associated Nephropathy / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentAids / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentChronic Hepatitis B Infection5
3CompletedTreatmentHIV-1 Infections2
3CompletedTreatmentHepatitis B,Chronic2
3CompletedTreatmentHepatitis B / Liver Cirrhosis1
3CompletedTreatmentHepatitis / Hepatitis B,Chronic / Liver Cirrhosis1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections44
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I2
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3CompletedTreatmentInfection, Human Immunodeficiency Virus I1
3RecruitingTreatmentAcute HIV Infection1
3RecruitingTreatmentAids1
3RecruitingTreatmentHIV-1 Infections / Tuberculosis1
3RecruitingTreatmentHepatitis B,Chronic1
3RecruitingTreatmentHepatitis B / Malignancies1
3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections4
3TerminatedPreventionDiarrhea1
3TerminatedTreatmentHIV Disease1
3TerminatedTreatmentHepatitis B1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentAcute HIV Infection1
3Unknown StatusTreatmentAids / Human Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentChronic HBV With Severe Exacerbation1
3Unknown StatusTreatmentHepatocellular Carcinomas / Recurrences1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections4
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4Active Not RecruitingTreatmentChronic Hepatitis B Infection1
4Active Not RecruitingTreatmentHIV Disease1
4Active Not RecruitingTreatmentHIV-1 Infections2
4Active Not RecruitingTreatmentHiv-positive / Malnourished1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4CompletedNot AvailableHIV Disease / Proteinuria1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections3
4CompletedBasic ScienceCardiovascular Diseases / Dyslipidemias / Glucose Metabolism Disorders / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Metabolic Diseases1
4CompletedDiagnosticCardiovascular Diseases / HIV-Associated Lipodystrophy Syndrome1
4CompletedDiagnosticHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedPreventionCentral Nervous System Diseases / Dementias / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionChronic Hepatitis B Infection / Complications / Late Pregnancy / Transmission1
4CompletedPreventionChronic Infection / Hepatitis B Infection / Viremia1
4CompletedPreventionHIV Disease1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections2
4CompletedTreatmentAcquired Immunodeficiency Syndromes1
4CompletedTreatmentAids / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentAids / Human Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal1
4CompletedTreatmentChronic Hepatitis B Infection5
4CompletedTreatmentCompensated Chronic Hepatitis B1
4CompletedTreatmentHIV Disease5
4CompletedTreatmentHIV Disease / Mitochondrial Toxicity1
4CompletedTreatmentHIV Disease / Tuberculosis1
4CompletedTreatmentHIV-1 Infections2
4CompletedTreatmentHIV/AIDS1
4CompletedTreatmentHemophilia A / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHepatitis B2
4CompletedTreatmentHepatitis B,Chronic5
4CompletedTreatmentHepatitis B / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections21
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
4RecruitingPreventionHIV-1 Infections1
4RecruitingPreventionHIV/AIDS and Infections1
4RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentChronic Hepatitis B Infection1
4RecruitingTreatmentHIV Disease1
4RecruitingTreatmentHepatitis B,Chronic1
4SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedDiagnosticAcidosis, Respiratory1
4TerminatedTreatmentChronic Hepatitis B Infection2
4TerminatedTreatmentHBsAg-positive Renal Allograft Recipients1
4TerminatedTreatmentHIV Disease1
4TerminatedTreatmentHepatitis, Chronic1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4Unknown StatusPreventionHIV-Associated Lipodystrophy Syndrome / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusTreatmentAcquired Immunodeficiency Syndromes1
4Unknown StatusTreatmentChronic Hepatitis B Infection4
4Unknown StatusTreatmentHepatitis B,Chronic2
4Unknown StatusTreatmentHiV1- Positive1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections4
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4WithdrawnTreatmentHepatitis B,Chronic2
Not AvailableActive Not RecruitingNot AvailableHIV-1 Infections1
Not AvailableActive Not RecruitingNot AvailableHepatitis B / Liver Cirrhosis1
Not AvailableCompletedNot AvailableAcute Liver Failure / Hepatitis B / Hepatocellular Carcinomas / Liver Cirrhosis1
Not AvailableCompletedNot AvailableHIV Disease / Kwashiorkor / Marasmus / Severe Acute Malnutrition1
Not AvailableCompletedNot AvailableHIV-1 Infections1
Not AvailableCompletedNot AvailableHepatitis B,Chronic1
Not AvailableCompletedPreventionHIV Disease1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentAntiretroviral Treatment Outcomes1
Not AvailableCompletedTreatmentHepatitis B,Chronic1
Not AvailableCompletedTreatmentHepatitis B / Neoplasms1
Not AvailableCompletedTreatmentHepatitis C / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections30
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis2
Not AvailableEnrolling by InvitationNot AvailableThe Safety of Anti-viral Drugs Used in Late Pregnancy1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableRecruitingBasic ScienceHIV Disease1
Not AvailableRecruitingTreatmentAcute HIV Infection / HIV Disease1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusTreatmentAIDS/HIV PROBLEM2
Not AvailableUnknown StatusTreatmentHBV Coinfection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusTreatmentHepatitis B1
Not AvailableUnknown StatusTreatmentHepatitis B / Liver Failure1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculous Meningitis1
Not AvailableWithdrawnTreatmentHepatitis B / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Pharmacoeconomics
Manufacturers
  • Viiv healthcare co
  • Glaxosmithkline
Packagers
Dosage forms
FormRouteStrength
SolutionOral10 mg
TabletOral150 mg
TabletOral300 mg
TabletOral
Tablet, film coatedOral
TabletOral300 mg/1
Tablet, film coatedOral150 mg
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral300 mg
SolutionOral5 mg/mL
Tablet, film coatedOral100 mg/1
SolutionOral5 mg
TabletOral100 mg
SolutionOral10 mg/mL
TabletOral150 mg/1
Tablet, film coatedOral300 mg/1
Tablet, film coatedOral100 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)
CA2070230 No2004-08-032012-06-02Canada
CA2100269 No1999-02-232012-01-03Canada
US5905082 Yes1996-11-182016-11-18Us
US6004968 Yes1998-09-202018-09-20Us
US6294540 Yes1998-11-142018-11-14Us
US6417191 Yes1996-09-282016-09-28Us
US7119202 No1992-08-082009-08-08Us
US7169780 No2003-10-032023-10-03Us
US7217713 No2002-10-212022-10-21Us
US7435734 No2002-10-212022-10-21Us
US7754731 No2009-03-112029-03-11Us
US7820660 No2003-04-252023-04-25Us
US8129385 No2007-10-052027-10-05Us
US9242986 No2009-10-082029-10-08Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point160-162 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassNucleoside and nucleotide analogues
Direct Parent3'-thia pyrimidine nucleosides
Alternative Parents
Substituents
  • 3'-thia pyrimidine nucleoside
  • Hydroxypyrimidine
  • Hydropyrimidine
  • Pyrimidine
  • Monothioacetal
  • Oxathiolane
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

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
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 ]
2. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
adduct
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 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. 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 ribonuclease H (RNase H) activity that cleaves the RNA strand of RNA-DNA heteroduplexes in a partially processive 3'- to 5'-endonucleasic mode. Neo-synthesized pregenomic RNA (pgRNA) are encapsidated to...
Gene Name:
P
Uniprot ID:
Q05486
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
Human
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 on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:
DCK
Uniprot ID:
P27707
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
Human
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 phosphate acceptors. Also displays broad nucleoside diphosphate kinase activity.
Gene Name:
CMPK1
Uniprot ID:
P30085
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
Human
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
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
Human
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-site intermediate. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities....
Gene Name:
NME1
Uniprot ID:
P15531
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
Human
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 DNA non-specifically (PubMed:8392752). Exhibits histidine protein kinase activity.
Gene Name:
NME2
Uniprot ID:
P22392
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
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Lipid binding
Specific Function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1A
Uniprot ID:
P49585
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
Human
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
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
Human
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
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 ]

Transporters

Kind
Protein
Organism
Human
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, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
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
Human
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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
Human
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 from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
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
Human
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-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 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
Human
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, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
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
Human
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
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
Human
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
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
Human
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
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
Human
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 hepatocytes (By similarity).
Gene Name:
ABCC3
Uniprot ID:
O15438
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
Human
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on April 29, 2017 08:03