Identification

Name
Lamivudine
Accession Number
DB00709  (APRD00681)
Type
Small Molecule
Groups
Approved, Investigational
Description

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

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
  • Lamivudin
  • Lamivudina
  • Lamivudine
  • Lamivudinum
External IDs
BCH 189, (-)- / GR 109714X / GR-109714X
Product Ingredients
IngredientUNIICASInChI Key
3-TCNot AvailableNot AvailableNot applicable
GR 109714 XNot AvailableNot AvailableNot applicable
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
3tcTablet300 mgOralViiV Healthcare ULC2003-09-09Not applicableCanada
3tcSolution10 mgOralViiV Healthcare ULC1995-12-31Not applicableCanada
3tcTablet150 mgOralViiV Healthcare ULC1995-12-31Not applicableCanada
CombivirTablet, film coated150 mg/1OralRemedy Repack2013-03-112016-12-09Us00173 0595 00 nlmimage10 10230838
EpivirTablet, film coated150 mg/1OralRebel Distributors1995-11-21Not applicableUs
EpivirTablet, film coated150 mg/1OralViiV Healthcare ULC2010-10-04Not applicableUs49702 0203 18 nlmimage10 2c19965c
EpivirTablet, film coated300 mg/1OralPhysicians Total Care, Inc.2007-09-28Not applicableUs
EpivirTablet, film coated300 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
EpivirTablet, film coated150 mgOralViiV Healthcare ULC1996-08-08Not applicableEu
EpivirTablet, film coated150 mgOralViiV Healthcare ULC1996-08-08Not applicableEu
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
Auro-lamivudineTablet300 mgOralAuro Pharma Inc2013-10-16Not applicableCanada
Auro-lamivudineTablet150 mgOralAuro Pharma Inc2013-10-16Not applicableCanada
LamivudineTablet300 mg/1OralIngenus Pharmaceuticals Llc2017-02-01Not applicableUs
LamivudineTablet, film coated100 mg/1OralMylan Pharmaceuticals2015-01-09Not applicableUs
LamivudineTablet, film coated150 mg/1OralStrides Shasun Limited2018-04-19Not applicableUs
LamivudineTablet, film coated150 mg/1OralAv Pak2015-07-30Not applicableUs
LamivudineTablet, film coated300 mg/1OralLupin Pharmaceuticals2015-03-25Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir Sulfate (600 mg/1)Tablet, film coatedOralAurobindo Pharma2017-03-28Not applicableUs
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir Sulfate (600 mg/1)Tablet, film coatedOralTeva2016-09-29Not applicableUs
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir Sulfate (600 mg/1)Tablet, film coatedOralRemedy Repack2017-08-28Not applicableUs
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir Sulfate (600 mg/1)Tablet, film coatedOralAv Kare, Inc.2018-02-21Not applicableUs
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir Sulfate (600 mg/1)Tablet, film coatedOralCipla Limited2017-03-28Not applicableUs
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir Sulfate (600 mg/1)Tablet, film coatedOralPrasco, Laboratories2016-09-29Not applicableUs
Abacavir and LamivudineLamivudine (300 mg/1) + Abacavir Sulfate (600 mg/1)Tablet, film coatedOralLupin Pharmaceuticals2017-03-28Not applicableUs
Abacavir Sulfate, Lamivudine and ZidovudineLamivudine (150 mg/1) + Abacavir Sulfate (300 mg/1) + Zidovudine (300 mg/1)TabletOralLupin Pharmaceuticals2013-12-17Not applicableUs
Abacavir, Lamivudine and ZidovudineLamivudine (150 mg/1) + Abacavir Sulfate (300 mg/1) + Zidovudine (300 mg/1)TabletOralLupin Pharmaceuticals2013-12-17Not applicableUs
Apo-abacavir-lamivudineLamivudine (300 mg) + Abacavir (600 mg)TabletOralApotex Corporation2016-03-15Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DutrebisLamivudine (150 mg) + Raltegravir potassium (300 mg)Tablet, film coatedOralMerck Sharp & Dohme Limited2015-03-262017-04-27Eu
International/Other Brands
Amilitrap (Dosa) / Antiheb (Mebiphar) / Avilam (Beximco) / Avolam (Ranbaxy Laboratories) / Epivir / 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)
Categories
UNII
2T8Q726O95
CAS number
134678-17-4
Weight
Average: 229.256
Monoisotopic: 229.052111923
Chemical Formula
C8H11N3O3S
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)[C@@H]1CS[C@H](CO)O1

Pharmacology

Indication

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

Associated Conditions
Pharmacodynamics

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

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
Human
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.

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]
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
DrugInteractionDrug group
AbemaciclibThe serum concentration of Lamivudine can be increased when it is combined with Abemaciclib.Approved, Investigational
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
AlectinibThe serum concentration of Lamivudine can be increased when it is combined with Alectinib.Approved, Investigational
Aluminium clofibrateThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Aluminium clofibrate.Experimental
AmantadineThe serum concentration of Lamivudine can be increased when it is combined with Amantadine.Approved
AmilorideThe serum concentration of Lamivudine can be increased when it is combined with Amiloride.Approved
Aminohippuric acidThe serum concentration of Lamivudine can be increased when it is combined with Aminohippuric acid.Approved, Investigational
AmiodaroneThe serum concentration of Lamivudine can be increased when it is combined with Amiodarone.Approved, Investigational
AmlodipineThe serum concentration of Lamivudine can be increased when it is combined with Amlodipine.Approved
AmodiaquineThe serum concentration of Lamivudine can be increased when it is combined with Amodiaquine.Approved, Investigational
AmoxapineThe serum concentration of Lamivudine can be increased when it is combined with Amoxapine.Approved
AmsacrineThe serum concentration of Lamivudine can be increased when it is combined with Amsacrine.Approved, Investigational
AnnamycinThe serum concentration of Lamivudine can be increased when it is combined with Annamycin.Investigational
ApalutamideThe serum concentration of Lamivudine can be decreased when it is combined with Apalutamide.Approved, Investigational
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
AtorvastatinThe serum concentration of Lamivudine can be increased when it is combined with Atorvastatin.Approved
AvatrombopagThe serum concentration of Lamivudine can be increased when it is combined with Avatrombopag.Approved, Investigational
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
Bafilomycin A1The serum concentration of Lamivudine can be increased when it is combined with Bafilomycin A1.Experimental
Bafilomycin B1The serum concentration of Lamivudine can be increased when it is combined with Bafilomycin B1.Experimental
BaricitinibThe serum concentration of Lamivudine can be increased when it is combined with Baricitinib.Approved, Investigational
BenzquinamideThe serum concentration of Lamivudine can be increased when it is combined with Benzquinamide.Withdrawn
Benzyl alcoholThe serum concentration of Lamivudine can be increased when it is combined with Benzyl alcohol.Approved
BepridilThe serum concentration of Lamivudine can be increased when it is combined with Bepridil.Approved, Withdrawn
BezafibrateThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Bezafibrate.Approved, Investigational
BicalutamideThe serum concentration of Lamivudine can be increased when it is combined with Bicalutamide.Approved
Biricodar dicitrateThe serum concentration of Lamivudine can be increased when it is combined with Biricodar dicitrate.Investigational
BoceprevirThe serum concentration of Lamivudine can be increased when it is combined with Boceprevir.Approved, Withdrawn
Brefeldin AThe serum concentration of Lamivudine can be increased when it is combined with Brefeldin A.Experimental
BrigatinibThe serum concentration of Lamivudine can be increased when it is combined with Brigatinib.Approved, Investigational
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
CannabidiolThe serum concentration of Lamivudine can be increased when it is combined with Cannabidiol.Approved, Investigational
CaptoprilThe serum concentration of Lamivudine can be increased when it is combined with Captopril.Approved
CarvedilolThe serum concentration of Lamivudine can be increased when it is combined with Carvedilol.Approved, Investigational
CefoperazoneThe serum concentration of Lamivudine can be increased when it is combined with Cefoperazone.Approved, Investigational
CeftriaxoneThe serum concentration of Lamivudine can be increased when it is combined with Ceftriaxone.Approved
CerivastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Lamivudine is combined with Cerivastatin.Approved, Withdrawn
ChloroformThe serum concentration of Lamivudine can be increased when it is combined with Chloroform.Vet Approved
ChlorphenamineThe serum concentration of Lamivudine can be increased when it is combined with Chlorphenamine.Approved
ChlorpromazineThe serum concentration of Lamivudine can be increased when it is combined with Chlorpromazine.Approved, Investigational, Vet Approved
ChlorprothixeneThe serum concentration of Lamivudine can be increased when it is combined with Chlorprothixene.Approved, Investigational, Withdrawn
CholineThe serum concentration of Lamivudine can be increased when it is combined with Choline.Approved, Nutraceutical
Choline salicylateThe serum concentration of Lamivudine can be increased when it is combined with Choline salicylate.Approved, Nutraceutical
CimetidineThe serum concentration of Lamivudine can be increased when it is combined with Cimetidine.Approved, Investigational
CiprofibrateThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Ciprofibrate.Approved, Investigational
CisplatinThe serum concentration of Lamivudine can be increased when it is combined with Cisplatin.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
ClofibrateThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Clofibrate.Approved, Investigational
ClofibrideThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Clofibride.Experimental
ClomipramineThe serum concentration of Lamivudine can be increased when it is combined with Clomipramine.Approved, Investigational, Vet Approved
CobicistatThe serum concentration of Lamivudine can be increased when it is combined with Cobicistat.Approved
CocaineThe serum concentration of Lamivudine can be increased when it is combined with Cocaine.Approved, Illicit
ColchicineThe serum concentration of Lamivudine can be increased when it is combined with Colchicine.Approved
Concanamycin AThe serum concentration of Lamivudine can be increased when it is combined with Concanamycin A.Experimental
ConivaptanThe serum concentration of Lamivudine can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe serum concentration of Lamivudine can be increased when it is combined with Crizotinib.Approved
CurcuminThe serum concentration of Lamivudine can be increased when it is combined with Curcumin.Approved, Investigational
CyclosporineThe serum concentration of Lamivudine can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
D-LevofloxacinThe serum concentration of Lamivudine can be increased when it is combined with D-Levofloxacin.Experimental
DabrafenibThe serum concentration of Lamivudine can be increased when it is combined with Dabrafenib.Approved, Investigational
DaclatasvirThe serum concentration of Lamivudine can be increased when it is combined with Daclatasvir.Approved, Investigational
DactinomycinThe serum concentration of Lamivudine can be increased when it is combined with Dactinomycin.Approved, Investigational
DaidzinThe serum concentration of Lamivudine can be increased when it is combined with Daidzin.Experimental
DasabuvirThe serum concentration of Lamivudine can be increased when it is combined with Dasabuvir.Approved
DaunorubicinThe serum concentration of Lamivudine can be increased when it is combined with Daunorubicin.Approved
DesipramineThe serum concentration of Lamivudine can be increased when it is combined with Desipramine.Approved, Investigational
DesmethylsertralineThe serum concentration of Lamivudine can be increased when it is combined with Desmethylsertraline.Experimental
DexamethasoneThe serum concentration of Lamivudine can be increased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
Dexchlorpheniramine maleateThe serum concentration of Lamivudine can be increased when it is combined with Dexchlorpheniramine maleate.Approved
DexniguldipineThe serum concentration of Lamivudine can be increased when it is combined with Dexniguldipine.Experimental
DexverapamilThe serum concentration of Lamivudine can be increased when it is combined with Dexverapamil.Experimental
Diethyl etherThe serum concentration of Lamivudine can be increased when it is combined with Diethyl ether.Experimental
DiethylstilbestrolThe serum concentration of Lamivudine can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
DihydroergotamineThe serum concentration of Lamivudine can be increased when it is combined with Dihydroergotamine.Approved, Investigational
DiltiazemThe serum concentration of Lamivudine can be increased when it is combined with Diltiazem.Approved, Investigational
DinoprostoneThe serum concentration of Lamivudine can be increased when it is combined with Dinoprostone.Approved
DiphenhydramineThe serum concentration of Lamivudine can be increased when it is combined with Diphenhydramine.Approved, Investigational
DipyridamoleThe serum concentration of Lamivudine can be increased when it is combined with Dipyridamole.Approved
DisopyramideThe serum concentration of Lamivudine can be increased when it is combined with Disopyramide.Approved
DofequidarThe serum concentration of Lamivudine can be increased when it is combined with Dofequidar.Experimental, Investigational
DolutegravirThe serum concentration of Lamivudine can be increased when it is combined with Dolutegravir.Approved
DopamineThe serum concentration of Lamivudine can be increased when it is combined with Dopamine.Approved
DovitinibThe serum concentration of Lamivudine can be increased when it is combined with Dovitinib.Investigational
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, 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
DuloxetineThe serum concentration of Lamivudine can be increased when it is combined with Duloxetine.Approved
EconazoleThe serum concentration of Lamivudine can be increased when it is combined with Econazole.Approved
ElacridarThe serum concentration of Lamivudine can be increased when it is combined with Elacridar.Investigational
EltrombopagThe serum concentration of Lamivudine can be increased when it is combined with Eltrombopag.Approved
EmopamilThe serum concentration of Lamivudine can be increased when it is combined with Emopamil.Experimental
EmtricitabineThe risk or severity of adverse effects can be increased when Lamivudine is combined with Emtricitabine.Approved, Investigational
EnasidenibThe serum concentration of Lamivudine can be increased when it is combined with Enasidenib.Approved, Investigational
EnzalutamideThe serum concentration of Lamivudine can be increased when it is combined with Enzalutamide.Approved
EpinephrineThe serum concentration of Lamivudine can be increased when it is combined with Epinephrine.Approved, Vet 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
ErlotinibThe serum concentration of Lamivudine can be increased when it is combined with Erlotinib.Approved, Investigational
ErythromycinThe serum concentration of Lamivudine can be increased when it is combined with Erythromycin.Approved, Investigational, Vet Approved
EsomeprazoleThe serum concentration of Lamivudine can be increased when it is combined with Esomeprazole.Approved, Investigational
EstradiolThe serum concentration of Lamivudine can be increased when it is combined with Estradiol.Approved, Investigational, Vet Approved
Estradiol acetateThe serum concentration of Lamivudine can be increased when it is combined with Estradiol acetate.Approved, Investigational, Vet Approved
Estradiol benzoateThe serum concentration of Lamivudine can be increased when it is combined with Estradiol benzoate.Approved, Investigational, Vet Approved
Estradiol cypionateThe serum concentration of Lamivudine can be increased when it is combined with Estradiol cypionate.Approved, Investigational, Vet Approved
Estradiol dienanthateThe serum concentration of Lamivudine can be increased when it is combined with Estradiol dienanthate.Approved, Investigational, Vet Approved
Estradiol valerateThe serum concentration of Lamivudine can be increased when it is combined with Estradiol valerate.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Lamivudine can be increased when it is combined with Estramustine.Approved, Investigational
EstroneThe serum concentration of Lamivudine can be increased when it is combined with Estrone.Approved
EtofibrateThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Etofibrate.Approved
EtoposideThe serum concentration of Lamivudine can be increased when it is combined with Etoposide.Approved
EzetimibeThe serum concentration of Lamivudine can be increased when it is combined with Ezetimibe.Approved
FamotidineThe serum concentration of Lamivudine can be increased when it is combined with Famotidine.Approved
FelodipineThe serum concentration of Lamivudine can be increased when it is combined with Felodipine.Approved, Investigational
FenofibrateThe serum concentration of Lamivudine can be increased when it is combined with Fenofibrate.Approved
Fenofibric acidThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Fenofibric acid.Approved
FentanylThe serum concentration of Lamivudine can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FluconazoleThe serum concentration of Lamivudine can be increased when it is combined with Fluconazole.Approved, Investigational
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, Investigational, 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, Investigational
FluvastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Lamivudine is combined with Fluvastatin.Approved
FluvoxamineThe serum concentration of Lamivudine can be increased when it is combined with Fluvoxamine.Approved, Investigational
FostamatinibThe serum concentration of Lamivudine can be increased when it is combined with Fostamatinib.Approved, Investigational
GallopamilThe serum concentration of Lamivudine can be increased when it is combined with Gallopamil.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
GemfibrozilThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Gemfibrozil.Approved
GenisteinThe serum concentration of Lamivudine can be increased when it is combined with Genistein.Investigational
GlecaprevirThe serum concentration of Lamivudine can be increased when it is combined with Glecaprevir.Approved, Investigational
GlyburideThe serum concentration of Lamivudine can be increased when it is combined with Glyburide.Approved
GlycerinThe serum concentration of Lamivudine can be increased when it is combined with Glycerin.Approved, Investigational
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.Approved, Investigational, Withdrawn
GuanidineThe serum concentration of Lamivudine can be increased when it is combined with Guanidine.Approved
HesperetinThe serum concentration of Lamivudine can be increased when it is combined with Hesperetin.Approved
HistamineThe serum concentration of Lamivudine can be increased when it is combined with Histamine.Approved, Investigational
HM-30181The serum concentration of Lamivudine can be increased when it is combined with HM-30181.Experimental
HycanthoneThe serum concentration of Lamivudine can be increased when it is combined with Hycanthone.Approved, Investigational
HydroxychloroquineThe serum concentration of Lamivudine can be increased when it is combined with Hydroxychloroquine.Approved
IbuprofenThe serum concentration of Lamivudine can be increased when it is combined with Ibuprofen.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 increased 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
IsradipineThe serum concentration of Lamivudine can be increased when it is combined with Isradipine.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, Investigational, Vet Approved
IvosidenibThe serum concentration of Lamivudine can be increased when it is combined with Ivosidenib.Approved, Investigational
KetoconazoleThe serum concentration of Lamivudine can be increased when it is combined with Ketoconazole.Approved, Investigational
LaniquidarThe serum concentration of Lamivudine can be increased when it is combined with Laniquidar.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
LedipasvirThe serum concentration of Lamivudine can be increased when it is combined with Ledipasvir.Approved
LenvatinibThe serum concentration of Lamivudine can be increased when it is combined with Lenvatinib.Approved, Investigational
LetermovirThe serum concentration of Lamivudine can be increased when it is combined with Letermovir.Approved, Investigational
LevofloxacinThe serum concentration of Lamivudine can be increased when it is combined with Levofloxacin.Approved, Investigational
LidocaineThe serum concentration of Lamivudine can be increased when it is combined with Lidocaine.Approved, Vet Approved
LinagliptinThe serum concentration of Lamivudine can be increased when it is combined with Linagliptin.Approved
LomerizineThe serum concentration of Lamivudine can be increased when it is combined with Lomerizine.Experimental
LomitapideThe serum concentration of Lamivudine can be increased when it is combined with Lomitapide.Approved, Investigational
LonafarnibThe serum concentration of Lamivudine can be increased when it is combined with Lonafarnib.Investigational
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, Investigational
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
LoxapineThe serum concentration of Lamivudine can be increased when it is combined with Loxapine.Approved
LumacaftorThe serum concentration of Lamivudine can be decreased when it is combined with Lumacaftor.Approved
LusutrombopagThe serum concentration of Lamivudine can be increased when it is combined with Lusutrombopag.Approved, Investigational
Medical CannabisThe serum concentration of Lamivudine can be increased when it is combined with Medical Cannabis.Experimental, Investigational
MefloquineThe serum concentration of Lamivudine can be increased when it is combined with Mefloquine.Approved, Investigational
Megestrol acetateThe serum concentration of Lamivudine can be increased when it is combined with Megestrol acetate.Approved, Investigational, Vet Approved
MetforminThe serum concentration of Lamivudine can be increased when it is combined with Metformin.Approved
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
MetronidazoleThe serum concentration of Lamivudine can be increased when it is combined with Metronidazole.Approved
MevastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Lamivudine is combined with Mevastatin.Experimental
MibefradilThe serum concentration of Lamivudine can be increased when it is combined with Mibefradil.Investigational, 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 increased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Lamivudine can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Lamivudine can be increased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Lamivudine can be increased when it is combined with Mitoxantrone.Approved, Investigational
MonensinThe serum concentration of Lamivudine can be increased when it is combined with Monensin.Vet Approved
NabiximolsThe serum concentration of Lamivudine can be increased when it is combined with Nabiximols.Approved, Investigational
NaringeninThe serum concentration of Lamivudine can be increased when it is combined with Naringenin.Experimental
NelfinavirThe serum concentration of Lamivudine can be increased when it is combined with Nelfinavir.Approved
NeratinibThe serum concentration of Lamivudine can be increased when it is combined with Neratinib.Approved, Investigational
NicardipineThe serum concentration of Lamivudine can be increased when it is combined with Nicardipine.Approved, Investigational
NicotineThe serum concentration of Lamivudine can be increased when it is combined with Nicotine.Approved
NigericinThe serum concentration of Lamivudine can be increased when it is combined with Nigericin.Experimental
NiguldipineThe serum concentration of Lamivudine can be increased when it is combined with Niguldipine.Experimental
NilotinibThe serum concentration of Lamivudine can be increased when it is combined with Nilotinib.Approved, Investigational
NimodipineThe serum concentration of Lamivudine can be increased when it is combined with Nimodipine.Approved, Investigational
NisoldipineThe serum concentration of Lamivudine can be increased when it is combined with Nisoldipine.Approved
NitrendipineThe serum concentration of Lamivudine can be increased when it is combined with Nitrendipine.Approved, Investigational
NorepinephrineThe serum concentration of Lamivudine can be increased when it is combined with Norepinephrine.Approved
NovobiocinThe serum concentration of Lamivudine can be increased when it is combined with Novobiocin.Approved, Investigational, Vet Approved
OmeprazoleThe serum concentration of Lamivudine can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
ONT-093The serum concentration of Lamivudine can be increased when it is combined with ONT-093.Investigational
OxprenololThe serum concentration of Lamivudine can be increased when it is combined with Oxprenolol.Approved
PaclitaxelThe serum concentration of Lamivudine can be increased when it is combined with Paclitaxel.Approved, Vet Approved
PaliperidoneThe serum concentration of Lamivudine can be increased when it is combined with Paliperidone.Approved
PantoprazoleThe serum concentration of Lamivudine can be increased when it is combined with Pantoprazole.Approved
ParitaprevirThe serum concentration of Lamivudine can be increased when it is combined with Paritaprevir.Approved, Investigational
ParoxetineThe serum concentration of Lamivudine can be increased when it is combined with Paroxetine.Approved, Investigational
PentazocineThe serum concentration of Lamivudine can be increased when it is combined with Pentazocine.Approved, Vet Approved
PethidineThe serum concentration of Lamivudine can be increased when it is combined with Pethidine.Approved
PhenforminThe serum concentration of Lamivudine can be increased when it is combined with Phenformin.Approved, Investigational, Withdrawn
PhenoxybenzamineThe serum concentration of Lamivudine can be increased when it is combined with Phenoxybenzamine.Approved
PibrentasvirThe serum concentration of Lamivudine can be increased when it is combined with Pibrentasvir.Approved, Investigational
PimagedineThe serum concentration of Lamivudine can be increased when it is combined with Pimagedine.Investigational
PimozideThe serum concentration of Lamivudine can be increased when it is combined with Pimozide.Approved
PitavastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Lamivudine is combined with Pitavastatin.Approved
PitolisantThe serum concentration of Lamivudine can be decreased when it is combined with Pitolisant.Approved, Investigational
PonatinibThe serum concentration of Lamivudine can be increased when it is combined with Ponatinib.Approved, Investigational
PosaconazoleThe serum concentration of Lamivudine can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Lamivudine 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
PrimaquineThe serum concentration of Lamivudine can be increased when it is combined with Primaquine.Approved
ProbenecidThe serum concentration of Lamivudine can be increased when it is combined with Probenecid.Approved, Investigational
ProcainamideThe serum concentration of Lamivudine can be increased when it is combined with Procainamide.Approved
ProgesteroneThe serum concentration of Lamivudine can be increased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Lamivudine can be increased when it is combined with Promethazine.Approved, Investigational
PropafenoneThe serum concentration of Lamivudine can be increased when it is combined with Propafenone.Approved
PropofolThe serum concentration of Lamivudine can be increased when it is combined with Propofol.Approved, Investigational, Vet 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, Investigational
QuinacrineThe serum concentration of Lamivudine can be increased when it is combined with Quinacrine.Approved, Investigational
QuinidineThe serum concentration of Lamivudine can be increased when it is combined with Quinidine.Approved, Investigational
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
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 increased when it is combined with Reserpine.Approved, Investigational
Reversin 121The serum concentration of Lamivudine can be increased when it is combined with Reversin 121.Experimental
RibavirinRibavirin may increase the hepatotoxic activities of Lamivudine.Approved
RifampicinThe serum concentration of Lamivudine can be increased 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 increased when it is combined with Ritonavir.Approved, Investigational
RonifibrateThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Ronifibrate.Experimental
RosuvastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Lamivudine is combined with Rosuvastatin.Approved
RucaparibThe serum concentration of Lamivudine can be increased when it is combined with Rucaparib.Approved, Investigational
SafinamideThe serum concentration of Lamivudine can be increased when it is combined with Safinamide.Approved, Investigational
SalinomycinThe serum concentration of Lamivudine can be increased when it is combined with Salinomycin.Vet Approved
SaquinavirThe serum concentration of Lamivudine can be increased when it is combined with Saquinavir.Approved, Investigational
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
SimfibrateThe risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Lamivudine is combined with Simfibrate.Experimental
SimvastatinThe risk or severity of myopathy and rhabdomyolysis can be increased when Lamivudine is combined with Simvastatin.Approved
SorafenibThe serum concentration of Lamivudine can be increased when it is combined with Sorafenib.Approved, Investigational
StaurosporineThe serum concentration of Lamivudine can be increased when it is combined with Staurosporine.Experimental
SulfasalazineThe serum concentration of Lamivudine can be increased when it is combined with Sulfasalazine.Approved
SunitinibThe serum concentration of Lamivudine can be increased when it is combined with Sunitinib.Approved, Investigational
SuvorexantThe serum concentration of Lamivudine can be increased when it is combined with Suvorexant.Approved, Investigational
TacrolimusThe serum concentration of Lamivudine can be increased when it is combined with Tacrolimus.Approved, Investigational
TafenoquineThe serum concentration of Lamivudine can be increased when it is combined with Tafenoquine.Approved, Investigational
TamoxifenThe serum concentration of Lamivudine can be increased when it is combined with Tamoxifen.Approved
TariquidarThe serum concentration of Lamivudine can be increased when it is combined with Tariquidar.Investigational
Taurocholic AcidThe serum concentration of Lamivudine can be increased when it is combined with Taurocholic Acid.Experimental
TelaprevirThe serum concentration of Lamivudine can be increased when it is combined with Telaprevir.Approved, Withdrawn
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
TerfenadineThe serum concentration of Lamivudine can be increased when it is combined with Terfenadine.Approved, Withdrawn
TeriflunomideThe serum concentration of Lamivudine can be increased when it is combined with Teriflunomide.Approved
TesmilifeneThe serum concentration of Lamivudine can be increased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Lamivudine can be increased when it is combined with Testosterone.Approved, Investigational
Testosterone cypionateThe serum concentration of Lamivudine can be increased when it is combined with Testosterone cypionate.Approved
Testosterone enanthateThe serum concentration of Lamivudine can be increased when it is combined with Testosterone enanthate.Approved
Testosterone undecanoateThe serum concentration of Lamivudine can be increased when it is combined with Testosterone undecanoate.Approved, Investigational
TetrandrineThe serum concentration of Lamivudine can be increased when it is combined with Tetrandrine.Experimental
ThiamineThe serum concentration of Lamivudine can be increased when it is combined with Thiamine.Approved, Investigational, Nutraceutical, Vet Approved
TicagrelorThe serum concentration of Lamivudine can be increased when it is combined with Ticagrelor.Approved
TipifarnibThe serum concentration of Lamivudine can be increased when it is combined with Tipifarnib.Investigational
TipiracilThe serum concentration of Tipiracil can be increased when it is combined with Lamivudine.Approved, Investigational
TipranavirThe serum concentration of Lamivudine can be increased when it is combined with Tipranavir.Approved, Investigational
TolvaptanThe serum concentration of Lamivudine can be increased when it is combined with Tolvaptan.Approved
TopiroxostatThe serum concentration of Lamivudine can be increased when it is combined with Topiroxostat.Approved, Investigational
ToremifeneThe serum concentration of Lamivudine can be increased when it is combined with Toremifene.Approved, Investigational
TrifluoperazineThe serum concentration of Lamivudine can be increased when it is combined with Trifluoperazine.Approved, Investigational
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
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
ValinomycinThe serum concentration of Lamivudine can be increased when it is combined with Valinomycin.Experimental
ValspodarThe serum concentration of Lamivudine can be increased when it is combined with Valspodar.Investigational
VandetanibThe serum concentration of Lamivudine can be increased when it is combined with Vandetanib.Approved
VelpatasvirThe serum concentration of Lamivudine can be increased when it is combined with Velpatasvir.Approved, Investigational
VemurafenibThe serum concentration of Lamivudine can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe serum concentration of Lamivudine can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Lamivudine can be increased when it is combined with Verapamil.Approved
VinblastineThe serum concentration of Lamivudine can be increased when it is combined with Vinblastine.Approved
VismodegibThe serum concentration of Lamivudine can be increased when it is combined with Vismodegib.Approved, Investigational
VoacamineThe serum concentration of Lamivudine can be increased when it is combined with Voacamine.Approved, Investigational
VorapaxarThe serum concentration of Lamivudine can be increased when it is combined with Vorapaxar.Approved
VoxilaprevirThe serum concentration of Lamivudine can be increased when it is combined with Voxilaprevir.Approved, Investigational
YohimbineThe serum concentration of Lamivudine can be increased when it is combined with Yohimbine.Approved, Investigational, Vet Approved
ZomepiracThe serum concentration of Lamivudine can be increased when it is combined with Zomepirac.Withdrawn
ZosuquidarThe serum concentration of Lamivudine can be increased when it is combined with Zosuquidar.Investigational
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
Human Metabolome Database
HMDB0014847
KEGG Drug
D00353
KEGG Compound
C07065
PubChem Compound
60825
PubChem Substance
46507855
ChemSpider
54812
BindingDB
50366817
ChEBI
63577
ChEMBL
CHEMBL141
Therapeutic Targets Database
DAP000167
PharmGKB
PA450163
HET
3TC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Lamivudine
ATC Codes
J05AR02 — Lamivudine and abacavirJ05AR13 — Lamivudine, abacavir and dolutegravirJ05AR12 — Lamivudine and tenofovir disoproxilJ05AR01 — Zidovudine and lamivudineJ05AR05 — Zidovudine, lamivudine and nevirapineJ05AR07 — Stavudine, lamivudine and nevirapineJ05AR04 — Zidovudine, lamivudine and abacavirJ05AR16 — Lamivudine and raltegravirJ05AR11 — Lamivudine, tenofovir disoproxil and efavirenzJ05AF05 — 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
0CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
1CompletedNot AvailableInfection, Human Immunodeficiency Virus I1
1CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
1CompletedOtherHIV-DDI1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
1CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHepatitis B Chronic Infection1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV)2
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections17
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pregnancy4
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
1RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
1Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections5
1, 2RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1, 2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2Unknown StatusTreatmentLiver Cirrhosis1
1, 2WithdrawnPreventionMalignant Lymphomas1
2Active Not RecruitingTreatmentAcute HIV Infection / HIV CNS Involvement1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
2CompletedPreventionHIV Prevention / HIV Transmission / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentGlomerulonephritis / Hepatitis B Chronic Infection / Hepatitis D, Chronic / Polyarteritis Nodosa1
2CompletedTreatmentHBV (Hepatitis B Virus) / Hepatitis / Viral Hepatitis B1
2CompletedTreatmentHBV / Hepatitis B Virus (HBV)1
2CompletedTreatmentHepatitis B Chronic Infection2
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections40
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
2CompletedTreatmentInfection, Human Immunodeficiency Virus I5
2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentViral Hepatitis B1
2RecruitingTreatmentHIV-1-infection1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2RecruitingTreatmentMetastatic Colorectal Cancers1
2SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
2TerminatedTreatmentInfection, Human Immunodeficiency Virus I2
2Unknown StatusPreventionHepatitis B Reactivation / Non-Hodgkin's Lymphoma (NHL)1
2Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Viral Hepatitis B1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2, 3CompletedTreatmentKaposi's Sarcoma AIDS Related1
2, 3CompletedTreatmentPrimary Biliary Cirrhosis (PBC)1
2, 3CompletedTreatmentTropical Spastic Paraparesis1
2, 3RecruitingTreatmentHepatocellular,Carcinoma1
2, 3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Pediatric AIDS1
2, 3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3Unknown StatusNot AvailableMalignant Lymphomas1
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentAcute HIV Infection1
3Active Not RecruitingTreatmentHepatitis B Chronic Infection1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I5
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I / Tuberculosis1
3CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionAcquired Immune Deficiency Syndrome (AIDS)1
3CompletedPreventionDisease Transmission, Vertical / Human Immunodeficiency Virus (HIV) Infections / Vertical Human Immunodeficiency Virus Transmission1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections4
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Plasmodium Infections1
3CompletedTreatmentAIDS-Associated Nephropathy / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHepatitis B Chronic Infection7
3CompletedTreatmentHepatitis / Hepatitis B Chronic Infection / Liver Cirrhosis1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections46
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 I4
3CompletedTreatmentLiver Cirrhosis / Viral Hepatitis B1
3CompletedTreatmentMalignancies / Viral Hepatitis B1
3RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
3RecruitingTreatmentAcute HIV Infection / Chronic Infection With HIV1
3RecruitingTreatmentHIV Seropositivity / HIV-1-infection / Human Immunodeficiency Virus (HIV) Infections2
3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
3SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedPreventionDiarrhea1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentViral Hepatitis B1
3Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentChronic HBV With Severe Exacerbation1
3Unknown StatusTreatmentHepatocellular,Carcinoma / Recurrences1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections4
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingPreventionInfection, Human Immunodeficiency Virus I1
4Active Not RecruitingTreatmentHepatitis B Chronic Infection1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections3
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Proteinuria1
4CompletedBasic ScienceCardiovascular Disease (CVD) / Dyslipidemias / Glucose Metabolism Disorders / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Metabolic Diseases1
4CompletedDiagnosticCardiovascular Disease (CVD) / HIV-Associated Lipodystrophy Syndrome1
4CompletedDiagnosticHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
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
4CompletedPreventionHuman Immunodeficiency Virus (HIV)1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections2
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal1
4CompletedTreatmentCompensated Chronic Hepatitis B1
4CompletedTreatmentHemophilia A / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHepatitis B Chronic Infection10
4CompletedTreatmentHiV1- Positive1
4CompletedTreatmentHiv-positive / Malnourished1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)6
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections20
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I2
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Mitochondrial Toxicity1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Tuberculosis1
4CompletedTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
4CompletedTreatmentInfection, Human Immunodeficiency Virus I3
4CompletedTreatmentViral Hepatitis B2
4Not Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV)1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingPreventionHIV/AIDS and Infections1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentHIV-1-infection / Solid Organ Transplant1
4RecruitingTreatmentHepatitis B Chronic Infection2
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedDiagnosticAcidosis, Respiratory1
4TerminatedTreatmentHBsAg-positive Renal Allograft Recipients1
4TerminatedTreatmentHepatitis B Chronic Infection2
4TerminatedTreatmentHepatitis, Chronic1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4Unknown StatusPreventionHIV-Associated Lipodystrophy Syndrome / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusTreatmentHepatitis B Chronic Infection6
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections4
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4WithdrawnTreatmentHepatitis B Chronic Infection2
Not AvailableActive Not RecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableActive Not RecruitingNot AvailableLiver Cirrhosis / Viral Hepatitis B1
Not AvailableCompletedNot AvailableFulminant Hepatic Failure / Hepatocellular,Carcinoma / Liver Cirrhosis / Viral Hepatitis B1
Not AvailableCompletedNot AvailableHepatitis B Chronic Infection1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Kwashiorkor / Marasmus / Severe Acute Malnutrition1
Not AvailableCompletedNot AvailableInfection, Human Immunodeficiency Virus I2
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentAntiretroviral Treatment Outcomes1
Not AvailableCompletedTreatmentHepatitis B Chronic Infection1
Not AvailableCompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections30
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis2
Not AvailableCompletedTreatmentNeoplasms / Viral Hepatitis B1
Not AvailableEnrolling by InvitationNot AvailableThe Safety of Anti-viral Drugs Used in Late Pregnancy1
Not AvailableNot Yet RecruitingNot AvailableChronic Lymphocytic Leukaemia (CLL)1
Not AvailableNot Yet RecruitingTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableRecruitingBasic ScienceHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingTreatmentAcute HIV Infection / Human Immunodeficiency Virus (HIV)1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableTerminatedNot AvailableHepatocellular,Carcinoma1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusTreatmentAIDS/HIV PROBLEM2
Not AvailableUnknown StatusTreatmentHBV Coinfection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusTreatmentHepatic Failure / Viral Hepatitis B1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculous Meningitis1
Not AvailableUnknown StatusTreatmentViral Hepatitis B1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1

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
SolutionOral10 mg
TabletOral150 mg
TabletOral300 mg
TabletOral
SolutionOral10 mg/ml
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
TabletOral150 mg/1
Tablet, film coatedOral300 mg/1
Tablet, film coatedOral
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)
US7119202No1992-08-082009-08-08Us
CA2070230No2004-08-032012-06-02Canada
CA2100269No1999-02-232012-01-03Canada
US9242986No2009-10-082029-10-08Us
US5905082Yes1996-11-182016-11-18Us
US6004968Yes1998-09-202018-09-20Us
US6294540Yes1998-11-142018-11-14Us
US7217713Yes2003-04-212023-04-21Us
US7435734Yes2003-04-212023-04-21Us
US7754731Yes2009-09-112029-09-11Us
US7169780Yes2004-04-032024-04-03Us
US6417191Yes1996-09-282016-09-28Us
US8129385No2007-10-052027-10-05Us
US7820660No2003-04-252023-04-25Us

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

Taxonomy

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 / Hydroxypyrimidine / Hydropyrimidine / Pyrimidine / Monothioacetal / Oxathiolane / Heteroaromatic compound / Azacycle / Organoheterocyclic compound / Oxacycle
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
primary alcohol, oxacycle, monothioacetal (CHEBI:63577)

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]
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 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
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...
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
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...
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
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
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
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-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
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 ...
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
Human
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
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
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
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
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
Human
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
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, 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
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 ...
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
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 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
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-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
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, 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
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
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
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
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
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
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
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 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
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
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 August 15, 2018 09:44