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
3tcTablet150 mgOralViiV Healthcare ULC1995-12-31Not applicableCanada
3tcSolution10 mgOralViiV Healthcare ULC1995-12-31Not applicableCanada
Auro-lamivudineTablet300 mgOralAuro Pharma Inc2013-10-16Not applicableCanada
Auro-lamivudineTablet150 mgOralAuro Pharma Inc2013-10-16Not applicableCanada
EpivirTablet300 mg/1OralRemedy Repack2011-04-202017-11-16Us
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 coated150 mgOralViiV Healthcare ULC1996-08-08Not applicableEu
EpivirTablet, film coated150 mg/1OralRemedy Repack2011-07-132016-12-07Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-lamivudineTablet300 mgOralApotex Corporation2012-05-18Not applicableCanada
Apo-lamivudineTablet150 mgOralApotex Corporation2012-05-18Not applicableCanada
Apo-lamivudine HbvTablet100 mgOralApotex Corporation2012-09-21Not applicableCanada
LamivudineTablet, film coated150 mg/1OralAmerincan Health Packaging2012-02-01Not applicableUs
LamivudineTablet, film coated300 mg/1OralLupin Pharmaceuticals2015-03-25Not applicableUs
LamivudineTablet150 mg/1OralIngenus Pharmaceuticals Llc2017-02-01Not applicableUs
LamivudineTablet, film coated150 mg/1OralRemedy Repack2015-05-302017-04-14Us
LamivudineTablet, film coated100 mg/1OralMylan Pharmaceuticals2015-01-09Not applicableUs
LamivudineTablet300 mg/1OralAppco Pharma Llc2017-02-01Not applicableUs
LamivudineTablet, film coated150 mg/1OralAv Pak2015-07-30Not applicableUs
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)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
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 coatedOralCipla Limited2017-03-28Not 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 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 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
Apo-abacavir-lamivudine-zidovudineLamivudine (150 mg) + Abacavir (300 mg) + Zidovudine (300 mg)TabletOralApotex Corporation2015-12-28Not applicableCanada
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)[[email protected]@H]1CS[[email protected]](CO)O1

Pharmacology

Indication

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

Structured Indications
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
BupropionThe serum concentration of Lamivudine can be increased when it is combined with Bupropion.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
GanciclovirThe risk or severity of adverse effects can be increased when Ganciclovir is combined with Lamivudine.Approved, Investigational
LumacaftorThe serum concentration of Lamivudine can be decreased when it is combined with Lumacaftor.Approved
RanolazineThe serum concentration of Lamivudine can be increased when it is combined with Ranolazine.Approved, Investigational
RibavirinRibavirin may increase the hepatotoxic activities of Lamivudine.Approved
RolapitantThe serum concentration of Lamivudine can be increased when it is combined with Rolapitant.Approved
TeriflunomideThe serum concentration of Lamivudine can be increased when it is combined with Teriflunomide.Approved
TrimethoprimTrimethoprim may decrease the excretion rate of Lamivudine which could result in a higher serum level.Approved, Vet Approved
ValganciclovirThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Lamivudine.Approved, 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
HMDB14847
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 nevirapineJ05AR04 — Zidovudine, lamivudine and abacavirJ05AR07 — Stavudine, lamivudine and nevirapineJ05AF05 — LamivudineJ05AR16 — Lamivudine and raltegravirJ05AR11 — Lamivudine, tenofovir disoproxil and efavirenz
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,Chronic1
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, 2CompletedTreatmentChronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections5
1, 2Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1, 2Unknown StatusTreatmentLiver Cirrhosis1
1, 2WithdrawnPreventionMalignant Lymphomas1
2Active Not RecruitingTreatmentAcute HIV Infection / HIV CNS Involvement1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentChronic Hepatitis B Infection1
2CompletedTreatmentChronic Hepatitis B Infection / Chronic Hepatitis D / Glomerulonephritis / Polyarteritis Nodosa1
2CompletedTreatmentHBV (Hepatitis B Virus) / Hepatitis / Viral Hepatitis B1
2CompletedTreatmentHBV / Hepatitis B Virus (HBV)1
2CompletedTreatmentHepatitis B,Chronic1
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
2Not Yet RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
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 StatusPreventionHIV Transmission / Human Immunodeficiency Virus (HIV) Infections1
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 RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I6
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
3CompletedTreatmentChronic Hepatitis B Infection5
3CompletedTreatmentHepatitis B,Chronic2
3CompletedTreatmentHepatitis / Hepatitis B,Chronic / 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 I3
3CompletedTreatmentLiver Cirrhosis / Viral Hepatitis B1
3CompletedTreatmentMalignancies / Viral Hepatitis B1
3Not Yet RecruitingTreatmentHIV Seropositivity / HIV-1-infection / Human Immunodeficiency Virus (HIV) Infections2
3RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
3RecruitingTreatmentAcute HIV Infection1
3RecruitingTreatmentHepatitis B,Chronic1
3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
3RecruitingTreatmentInfection, Human Immunodeficiency Virus I / Tuberculosis1
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 StatusTreatmentAcute HIV Infection1
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 RecruitingPreventionInfection, Human Immunodeficiency Virus I1
4Active Not RecruitingTreatmentChronic Hepatitis B Infection1
4Active Not RecruitingTreatmentHiv-positive / Malnourished1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)2
4Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I2
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 Hepatitis B Infection / Complications / Late Pregnancy / Transmission1
4CompletedPreventionChronic Infection / Hepatitis B Infection / Viral sepsis1
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
4CompletedTreatmentChronic Hepatitis B Infection5
4CompletedTreatmentCompensated Chronic Hepatitis B1
4CompletedTreatmentHIV / AIDS1
4CompletedTreatmentHemophilia A / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHepatitis B,Chronic5
4CompletedTreatmentHiV1- Positive1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)5
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 Type 1 (HIV-1)2
4CompletedTreatmentInfection, Human Immunodeficiency Virus I2
4CompletedTreatmentViral Hepatitis B2
4Not Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV)1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
4RecruitingPreventionHIV/AIDS and Infections1
4RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentChronic Hepatitis B Infection1
4RecruitingTreatmentHepatitis B,Chronic1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedDiagnosticAcidosis, Respiratory1
4TerminatedTreatmentChronic Hepatitis B Infection2
4TerminatedTreatmentHBsAg-positive Renal Allograft Recipients1
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 StatusTreatmentChronic Hepatitis B Infection4
4Unknown StatusTreatmentHepatitis B,Chronic2
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections4
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4WithdrawnTreatmentHepatitis B,Chronic2
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,Chronic1
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 AvailableCompletedTreatmentChronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHepatitis B,Chronic1
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 AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
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
Dosage forms
FormRouteStrength
SolutionOral10 mg
TabletOral150 mg
TabletOral300 mg
TabletOral
TabletOral300 mg/1
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral150 mg
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 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 November 19, 2017 20:33