Identification

Name
Emtricitabine
Accession Number
DB00879  (APRD00226)
Type
Small Molecule
Groups
Approved, Investigational
Description

Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) for the treatment of HIV infection in adults. Emtricitabine is an analogue of cytidine. The drug works by inhibiting reverse transcriptase, the enzyme that copies HIV RNA into new viral DNA.

Structure
Thumb
Synonyms
  • (−)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • (−)-2'-deoxy-5-fluoro-3'-thiacytidine
  • (−)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one
  • (−)-FTC
  • (−)-β-2',3'-dideoxy-5-fluoro-3'-thiacytidine
  • (2R-cis)-4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone
  • 4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one
  • 4-Amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1H-pyrimidin-2-one
  • 5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine
  • Emtricitabin
  • Emtricitabina
  • Emtricitabine
  • Emtricitabinum
External IDs
524-W-91 / 524W91 / BW-524W91
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EmtrivaCapsule200 mg/1OralPhysicians Total Care, Inc.2003-07-10Not applicableUs
EmtrivaCapsule200 mgOralGilead Sciences2006-03-03Not applicableCanada
EmtrivaCapsule200 mg/1OralGilead Sciences2003-07-02Not applicableUs
EmtrivaCapsule200 mg/1OralExcella Gmb H2003-07-02Not applicableUs
EmtrivaCapsule200 mg/1OralRemedy Repack2008-05-172017-04-28Us
EmtrivaCapsule200 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
EmtrivaSolution10 mg/1mLOralGilead Sciences2005-09-28Not applicableUs
TruvadaTablet, film coated200 mg/1OralRemedy Repack2013-04-032014-04-03Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-efavirenz-emtricitabine-tenofovirEmtricitabine (200 mg) + Efavirenz (600 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralApotex CorporationNot applicableNot applicableCanada
Apo-emtricitabine-tenofovirEmtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralApotex Corporation2017-07-26Not applicableCanada
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2012-10-16Not applicableUs
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-20Not applicableUs
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-20Not applicableUs
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralLake Erie Medical Dba Quality Care Produts Llc2006-07-202014-12-31Us
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralRemedy Repack2017-03-29Not applicableUs
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralAvera McKennan Hospital2015-03-062018-06-18Us
AtriplaEmtricitabine (200 mg) + Efavirenz (600 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralGilead Sciences, Llc2007-10-23Not applicableCanada
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralDoh Central Pharmacy2009-07-01Not applicableUs
International/Other Brands
Coviracil
Categories
UNII
G70B4ETF4S
CAS number
143491-57-0
Weight
Average: 247.247
Monoisotopic: 247.042690096
Chemical Formula
C8H10FN3O3S
InChI Key
XQSPYNMVSIKCOC-NTSWFWBYSA-N
InChI
InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1
IUPAC Name
4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
SMILES
NC1=NC(=O)N(C=C1F)[C@@H]1CS[C@H](CO)O1

Pharmacology

Indication

Indicated, in combination with other antiretroviral agents, for the treatment of HIV-1 infection in adults and for postexposure prophylaxis of HIV infection in health care workers and others exposed occupationally or nonoccupationally via percutaneous injury or mucous membrane or nonintact skin contact with blood, tissues, or other body fluids associated with risk for transmission of the virus.

Associated Conditions
Pharmacodynamics

Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Emtricitabine helps to block HIV reverse transcriptase, a chemical in your body (enzyme) that is needed for HIV to multiply. Emtricitabine is always used with other anti-HIV medicines to treat people with HIV infection. Emtricitabine may lower the amount of HIV in the blood (viral load). Emtricitabine may also help to increase the number of T cells called CD4 cells. Lowering the amount of HIV in the blood lowers the chance of death or infections that happen when your immune system is weak (opportunistic infections). People taking emtricitabine may still get opportunistic infections or other conditions that happen with HIV infection.

Mechanism of action

Emtricitabine works by inhibiting reverse transcriptase, the enzyme that copies HIV RNA into new viral DNA. Emtricitabine is a synthetic nucleoside analogue of cytidine. It is phosphorylated by cellular enzymes to form emtricitabine 5'-triphosphate, which is responsible for the inhibition of HIV-1 reverse transcriptase. It competes with the natural substrate deoxycytidine 5'-triphosphate and incorporates into nascent viral DNA, resulting in early chain termination. Therefore emtricitabine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate deoxycytidine 5'-triphosphate and by its incorporation into viral DNA. By inhibiting HIV-1 reverse transcriptase, emtricitabine can help to lower the amount of HIV, or "viral load", in a patient's body and can indirectly increase the number of immune system cells (called T cells or CD4+ T-cells). Both of these changes are associated with healthier immune systems and decreased likelihood of serious illness.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
Absorption

Rapidly absorbed (mean absolute bioavailability of 93% for capsules, and 75% for solution). Food does not effect absorption.

Volume of distribution
Not Available
Protein binding

Very low (less than 4%)

Metabolism

Minimally transformed (13%), most appears unchanged in urine (86%). The biotransformation of emtricitabine includes oxidation of the thiol moiety to form the 3′-sulfoxide diastereomers (~ 9% of dose) and conjugation with glucuronic acid to form 2′-O-glucuronide (~ 4% of dose). In vitro studies indicate emtricitabine is not an inhibitor or cytochrome P450 enzymes.

Route of elimination

The renal clearance of emtricitabine is greater than the estimated creatinine clearance, suggesting elimination by both glomerular filtration and active tubular secretion.

Half life

10 hours

Clearance
  • 302 +/- 94 mL/min [Renal Function Creatinine Clearance>80 ml/min]
  • 168 +/- 10 mL/min [Renal Function Creatinine Clearance 50-80 ml/min]
  • 138 +/- 28 mL/min [Renal Function Creatinine Clearance 30-49 ml/min]
  • 99 +/- 6 mL/min [Renal Function Creatinine Clearance<30 ml/min]
  • 64 +/- 12 mL/min [ESRD patients requiring dialysis]
Toxicity

Symptoms of overdose include serious liver problems (hepatotoxicity, with liver enlargement and fat in the liver called steatosis) or a lactic acidosis (buildup of an acid in the blood).

Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategory
Emtricitabine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
GanciclovirThe risk or severity of cytopenia can be increased when Ganciclovir is combined with Emtricitabine.
LamivudineThe risk or severity of adverse effects can be increased when Lamivudine is combined with Emtricitabine.
RibavirinRibavirin may increase the hepatotoxic activities of Emtricitabine.
ValganciclovirThe risk or severity of cytopenia can be increased when Valganciclovir is combined with Emtricitabine.
Varicella Zoster Vaccine (Live/Attenuated)The therapeutic efficacy of Varicella Zoster Vaccine (Live/Attenuated) can be decreased when used in combination with Emtricitabine.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference
US5538975
General References
  1. Masho SW, Wang CL, Nixon DE: Review of tenofovir-emtricitabine. Ther Clin Risk Manag. 2007 Dec;3(6):1097-104. [PubMed:18516268]
  2. Long MC, King JR, Acosta EP: Pharmacologic aspects of new antiretroviral drugs. Curr HIV/AIDS Rep. 2009 Feb;6(1):43-50. [PubMed:19149996]
  3. Authors unspecified: Emtricitabine/tenofovir disoproxil fumarate. Drugs R D. 2004;5(3):160-1. [PubMed:15139777]
  4. Goicoechea M, Best B: Efavirenz/emtricitabine/tenofovir disoproxil fumarate fixed-dose combination: first-line therapy for all? Expert Opin Pharmacother. 2007 Feb;8(3):371-82. [PubMed:17266471]
External Links
Human Metabolome Database
HMDB0015017
KEGG Drug
D01199
KEGG Compound
C12599
PubChem Compound
60877
PubChem Substance
46507606
ChemSpider
54859
BindingDB
50046283
ChEBI
31536
ChEMBL
CHEMBL885
Therapeutic Targets Database
DAP001084
PharmGKB
PA10069
HET
ETV
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Emtricitabine
ATC Codes
J05AR03 — Tenofovir disoproxil and emtricitabineJ05AR18 — Emtricitabine, tenofovir alafenamide, elvitegravir and cobicistatJ05AR19 — Emtricitabine, tenofovir alafenamide and rilpivirineJ05AR06 — Emtricitabine, tenofovir disoproxil and efavirenzJ05AR17 — Emtricitabine and tenofovir alafenamideJ05AR09 — Emtricitabine, tenofovir disoproxil, elvitegravir and cobicistatJ05AR08 — Emtricitabine, tenofovir disoproxil and rilpivirineJ05AF09 — Emtricitabine
AHFS Codes
  • 08:18.08.20 — Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
PDB Entries
2no6
FDA label
Download (328 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedOtherContraception / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
0CompletedOtherHealthy Volunteers1
0CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
1Active Not RecruitingBasic ScienceHealthy Volunteers1
1CompletedNot AvailableAcquired Immune Deficiency Syndrome (AIDS)1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV)2
1CompletedBasic ScienceHIV Prevention1
1CompletedBasic ScienceHIV-1-infection1
1CompletedBasic ScienceTuberculosis Infection1
1CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV)2
1CompletedOtherHIV-DDI1
1CompletedPreventionHuman Immunodeficiency Virus (HIV)1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections4
1CompletedTreatmentInsulin Resistance1
1Not Yet RecruitingOtherHIV Prevention / Medication Adherence1
1RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
1RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
1RecruitingTreatmentInsulin Resistance1
1, 2CompletedOtherPrEP Adherence Monitoring1
1, 2CompletedTreatmentAcute HIV Infection1
1, 2CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2Not Yet RecruitingTreatmentAicardi Goutières Syndrome1
2Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
2Active Not RecruitingTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedOtherInfection, Human Immunodeficiency Virus I1
2CompletedPreventionAmphetamine-Related Disorders / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHIV Prevention / HIV Transmission / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHIV Seroconversion / Stimulant Abuse1
2CompletedPreventionHIV Seropositivity1
2CompletedPreventionHepatitis B Chronic Infection1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections5
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) / Pregnancy1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentAntiretroviral Naive / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentHepatitis B Chronic Infection3
2CompletedTreatmentHepatitis B Virus (HBV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections11
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lymphoma, AIDS Related1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
2CompletedTreatmentInfection, Human Immunodeficiency Virus I6
2Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
2TerminatedTreatmentViral Hepatitis B1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
2WithdrawnPreventionHIV-1-infection1
2WithdrawnTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
2, 3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
2, 3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
2, 3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentAcute HIV Infection1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1
2, 3RecruitingOtherHIV-1-infection1
2, 3RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) / STI1
3Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV)1
3Active Not RecruitingTreatmentHIV-1-infection1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)3
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections2
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus-type 1 Infection1
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I12
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I / Kaposi s Sarcoma (KS)1
3Active Not RecruitingTreatmentPre-Exposure Prophylaxis of HIV-1 Infection1
3CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections5
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections6
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1)1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHBV / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentHepatitis B Chronic Infection2
3CompletedTreatmentHepatitis C Virus (HCV) Infection / Infection, Human Immunodeficiency Virus I1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections16
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections6
3CompletedTreatmentInfection, Human Immunodeficiency Virus I8
3CompletedTreatmentViral Hepatitis B1
3Enrolling by InvitationTreatmentHIV Risk1
3Not Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections / Stimulant Use / Substance Use Disorder (SUD)1
3Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
3Not Yet RecruitingTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
3RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3RecruitingTreatmentHIV-1/HBV Co-Infection1
3RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
3SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV)2
3TerminatedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Infection NOS1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3WithdrawnPreventionBreastfeeding / Human Immunodeficiency Virus (HIV) Infections / Pregnancy1
4Active Not RecruitingOtherHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4Active Not RecruitingPreventionInfection, Human Immunodeficiency Virus I1
4Active Not RecruitingTreatmentChronic Infection With HIV1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)2
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
4CompletedNot AvailableHealthy Volunteers2
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Proteinuria1
4CompletedNot AvailablePharmacokinetic Study in Healthy Volunteers1
4CompletedBasic ScienceHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
4CompletedOtherAdherence to Medication Regime1
4CompletedOtherAdherence, Medication / HIV Prevention / Pre-Exposure Prophylaxis / Risk Behaviors1
4CompletedOtherHealthy Volunteers1
4CompletedPreventionAdolescent Behaviors / Gender / Human Immunodeficiency Virus (HIV)1
4CompletedPreventionHIV Prevention1
4CompletedPreventionHuman Immunodeficiency Virus (HIV)6
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections3
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Sleep disorders and disturbances1
4CompletedTreatmentAcute HIV Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentCardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentDyslipidemias / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentHIV Associated Neurocognitive Disorders (HAND) / Neurocognitive Decline1
4CompletedTreatmentHIV, Combination Therapy1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHepatitis C Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)7
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections17
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B2
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)4
4CompletedTreatmentInfection, Human Immunodeficiency Virus I5
4Enrolling by InvitationPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4Not Yet RecruitingTreatmentAcute HIV Infection1
4Not Yet RecruitingTreatmentHepatitis B Chronic Infection1
4Not Yet RecruitingTreatmentHepatitis B Chronic Infection / Pregnancy1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Menopause / Osteoporosis1
4RecruitingOtherPre-Exposure Prophylaxis / Transgender Persons1
4RecruitingPreventionBone Demineralization1
4RecruitingPreventionHIV, Prevention1
4RecruitingPreventionHuman Immunodeficiency Virus (HIV)1
4RecruitingPreventionPrEP Adherence Monitoring1
4RecruitingSupportive CareHuman Immunodeficiency Virus (HIV)1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentBone Diseases, Metabolic / Chronic Hepatitis C Virus (HCV) Infection / Co-Infection / HIV-1-infection / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Intravenous Drug Usage / Methadone Dependence / Opioid Dependence / Substance Abuse1
4RecruitingTreatmentHIV-1-infection1
4RecruitingTreatmentHIV-1-infection / Solid Organ Transplant1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV)2
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Severe Immunosuppression1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Renal Insufficiency,Chronic / Therapeutic Agent Toxicity1
4TerminatedPreventionHuman Immunodeficiency Virus (HIV)1
4TerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV)2
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Osteopenia1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
4Unknown StatusBasic ScienceHuman Immunodeficiency Virus (HIV)1
4Unknown StatusPreventionHepatitis B Chronic Infection / Pregnancy1
4Unknown StatusPreventionHuman Immunodeficiency Virus (HIV)1
4Unknown StatusTreatmentHepatitis B Chronic Infection1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV)1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections2
4WithdrawnTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
4WithdrawnTreatmentViral Hepatitis B1
Not AvailableActive Not RecruitingPreventionHuman Immunodeficiency Virus (HIV)2
Not AvailableActive Not RecruitingTreatmentAnti-Retroviral Agents / Dyslipidemias / Efavirenz / HIV-1-infection / Rilpivirine / Sustained Virologic Response1
Not AvailableCompletedNot AvailableHIV Seropositivity / Pregnancy, High-Risk1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV)2
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections4
Not AvailableCompletedNot AvailableInfection, Human Immunodeficiency Virus I1
Not AvailableCompletedBasic ScienceHealthy Volunteers / Pharmacokinetics1
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV)2
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV)3
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections3
Not AvailableCompletedPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentPrimary Biliary Cholangitis1
Not AvailableNot Yet RecruitingNot AvailableHIV-1-infection1
Not AvailableNot Yet RecruitingPreventionInfection, Human Immunodeficiency Virus I1
Not AvailableRecruitingNot AvailableBone Diseases / Chronic Hepatitis B in HIV Patient / Kidney Injury1
Not AvailableRecruitingNot AvailableHIV Chemoprophylaxis / HIV Preexposure Prophylaxis1
Not AvailableRecruitingNot AvailableHIV Prevention1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV)2
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) / Illicit Drug User1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Inflammation Vagina / Menopause1
Not AvailableRecruitingBasic ScienceHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingPreventionHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedPreventionHuman Immunodeficiency Virus (HIV)1
Not AvailableTerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Tuberculosis Infection1
Not AvailableUnknown StatusBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections / Immune Reconstitution Inflammatory Syndrome1
Not AvailableWithdrawnNot AvailableHIV-infected Patients1
Not AvailableWithdrawnNot AvailableHuman Immunodeficiency Virus (HIV)1
Not AvailableWithdrawnBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) / Infertilities1

Pharmacoeconomics

Manufacturers
  • Gilead sciences inc
Packagers
  • Abbott Laboratories Ltd.
  • Excella GmbH
  • Gilead Sciences Inc.
  • Kaiser Foundation Hospital
  • Quality Care
  • Remedy Repack
  • Synthetics China
Dosage forms
FormRouteStrength
CapsuleOral200 mg/1
CapsuleOral200 mg
SolutionOral10 mg/1mL
TabletOral
Tablet, film coatedOral
Tablet, film coatedOral200 mg/1
Prices
Unit descriptionCostUnit
Emtriva 200 mg capsule21.75USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7402588No1993-02-012010-02-01Us
CA2075189No2004-11-302011-01-31Canada
US7800788No2002-02-022022-02-02Us
US5914331Yes1998-01-022018-01-02Us
US6043230Yes1998-01-252018-01-25Us
US5814639Yes1997-03-292017-03-29Us
US6939964Yes1998-07-202018-07-20Us
US6639071Yes1998-08-142018-08-14Us
US6642245Yes2001-05-042021-05-04Us
US6703396Yes2001-09-092021-09-09Us
US5922695Yes1998-01-252018-01-25Us
US5935946Yes1998-01-252018-01-25Us
US5977089Yes1998-01-252018-01-25Us
US8592397No2004-01-132024-01-13Us
US8716264No2004-01-132024-01-13Us
US9018192No2006-06-132026-06-13Us
US8598185No2008-05-012028-05-01Us
US7470506Yes1999-12-232019-12-23Us
US8597876Yes1999-12-232019-12-23Us
US7700645Yes2007-06-262027-06-26Us
US8518987Yes2004-08-162024-08-16Us
US7125879No2002-08-092022-08-09Us
US6838464No2001-02-262021-02-26Us
US8080551No2003-04-112023-04-11Us
US8101629No2002-08-092022-08-09Us
US7067522No1999-12-202019-12-20Us
US8148374No2009-09-032029-09-03Us
US7635704No2006-10-262026-10-26Us
US7176220No2003-11-202023-11-20Us
US8981103No2006-10-262026-10-26Us
US8633219No2010-04-242030-04-24Us
US8841310No2005-12-092025-12-09Us
US9296769No2012-08-152032-08-15Us
US7803788No2002-02-022022-02-02Us
US8754065No2012-08-152032-08-15Us
US7390791No2002-05-072022-05-07Us
US9545414No2006-06-132026-06-13Us
US9457036No2004-01-132024-01-13Us
US9744181No2004-01-132024-01-13Us
US9891239No2009-09-032029-09-03Us
US9889115No1999-06-232019-06-23Us
US9216996No2013-12-192033-12-19Us
US9708342No2015-06-192035-06-19Us
US9732092No2013-12-192033-12-19Us
US10039718No2012-10-042032-10-04Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)136-140 °CNot Available
water solubility112 mg/mLNot Available
logP-1.4Not Available
pKa2.65Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.0 mg/mLALOGPS
logP-0.8ALOGPS
logP-0.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)14.29ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.15 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.37 m3·mol-1ChemAxon
Polarizability21.79 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.9742
Caco-2 permeable-0.7053
P-glycoprotein substrateNon-substrate0.7363
P-glycoprotein inhibitor INon-inhibitor0.933
P-glycoprotein inhibitor IINon-inhibitor0.9806
Renal organic cation transporterNon-inhibitor0.8614
CYP450 2C9 substrateNon-substrate0.7945
CYP450 2D6 substrateNon-substrate0.8401
CYP450 3A4 substrateNon-substrate0.625
CYP450 1A2 substrateNon-inhibitor0.7748
CYP450 2C9 inhibitorNon-inhibitor0.7384
CYP450 2D6 inhibitorNon-inhibitor0.8666
CYP450 2C19 inhibitorNon-inhibitor0.7947
CYP450 3A4 inhibitorNon-inhibitor0.6915
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7653
Ames testAMES toxic0.5304
CarcinogenicityNon-carcinogens0.7394
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4133 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9861
hERG inhibition (predictor II)Non-inhibitor0.7827
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
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0900000000-70cf3fd58a0517da4a55
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0900000000-94b3e0720e27e6745a1f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0900000000-8dbfc14b46cc1f58e910
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0900000000-2dad282fe8707980881d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-1900000000-efef9ecafd739446f7ae
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-2900000000-349c2005cbcd9008b160
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-6dae6d5531a8a2f408cd
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-b8b0b2a41b04924a3ae6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-b0b20b1959137a52d9c7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-bd2c9f863694963a9078
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-1900000000-9903921aee7742b373e7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-1900000000-8857a02a53df79efbd5c

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
Pyrimidones / Aminopyrimidines and derivatives / Halopyrimidines / Aryl fluorides / Hydropyrimidines / Imidolactams / Oxathiolanes / Heteroaromatic compounds / Monothioacetals / Oxacyclic compounds
show 7 more
Substituents
3'-thia pyrimidine nucleoside / Aminopyrimidine / Halopyrimidine / Pyrimidone / Aryl fluoride / Aryl halide / Hydropyrimidine / Pyrimidine / Imidolactam / Heteroaromatic compound
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, pyrimidone, nucleoside analogue, monothioacetal (CHEBI:31536)

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. Modrzejewski KA, Herman RA: Emtricitabine: a once-daily nucleoside reverse transcriptase inhibitor. Ann Pharmacother. 2004 Jun;38(6):1006-14. Epub 2004 Apr 30. [PubMed:15121999]
  2. Bang LM, Scott LJ: Emtricitabine: an antiretroviral agent for HIV infection. Drugs. 2003;63(22):2413-24; discussion 2425-6. [PubMed:14609348]
  3. Molina JM, Cox SL: Emtricitabine: a novel nucleoside reverse transcriptase inhibitor. Drugs Today (Barc). 2005 Apr;41(4):241-52. [PubMed:16034488]

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. Bethell R, De Muys J, Lippens J, Richard A, Hamelin B, Ren C, Collins P: In vitro interactions between apricitabine and other deoxycytidine analogues. Antimicrob Agents Chemother. 2007 Aug;51(8):2948-53. Epub 2007 May 21. [PubMed:17517847]

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]

Drug created on June 13, 2005 07:24 / Updated on November 14, 2018 12:47