Identification

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

Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) indicated for the treatment of HIV infection in adults5 or combined with tenofovir alafenamide for the prevention of HIV-1 infection in high risk adolescents and adults.4 Emtricitabine is a cytidine analogue.5 The drug works by inhibiting HIV reverse transcriptase, preventing transcription of HIV RNA to DNA.5

Emtricitabine was granted FDA approval on 2 July 2003.5

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/1OralREMEDYREPACK INC.2019-02-04Not applicableUs
EmtrivaSolution10 mg/1mLOralGilead Sciences, Inc.2005-09-28Not applicableUs
EmtrivaCapsule200 mg/1OralGilead Sciences, Inc.2003-07-02Not applicableUs
EmtrivaCapsule200 mg/1OralRemedy Repack2008-05-172017-04-28Us
EmtrivaCapsule200 mg/1OralPhysicians Total Care, Inc.2003-07-10Not applicableUs
EmtrivaCapsule200 mg/1OralExcella Gmb H2003-07-02Not applicableUs
EmtrivaCapsule200 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
EmtrivaCapsule200 mgOralGilead Sciences2006-03-03Not applicableCanada
OdefseyTablet, film coatedOralGilead Sciences Ireland Uc2016-06-21Not applicableEu
OdefseyTablet, film coatedOralGilead Sciences Ireland Uc2016-06-21Not applicableEu
Additional Data Available
  • Application Number
    Application Number

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

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  • Product Code
    Product Code

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

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ag-emtricitabine / Tenofovir Disoproxil FumarateEmtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralAngita Pharma Inc.Not applicableNot applicableCanada
Apo-efavirenz-emtricitabine-tenofovirEmtricitabine (200 mg) + Efavirenz (600 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralApotex Corporation2018-09-04Not applicableCanada
Apo-emtricitabine-tenofovirEmtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralApotex Corporation2017-07-26Not applicableCanada
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 coatedOralPhysicians Total Care, Inc.2012-10-16Not 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/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralDoh Central Pharmacy2009-07-01Not applicableUs
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralREMEDYREPACK INC.2017-03-20Not 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 coatedOralA-S Medication Solutions2006-07-20Not 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

Emtricitabine is indicated in combination with other medications for the treatment of HIV-1 infections;5,9 treatment of HIV-1 infections in pediatric patients 25-35kg, treatment of HIV-1 infections in adult patients ≥35kg, for pre exposure prophylaxis of HIV-1 in adolescent and adult patients excluding those who have receptive vaginal sex;6,4 treatment of HIV-1 infections in pediatric and adult patients ≥17kg, pre exposure prophylaxis in adolescents and adults ≥35kg;8 treatment of HIV-1 in patients ≥12 years and ≥35kg;10 treatment of HIV-1 in patients weighing ≥35kg;11,13 treatment of HIV-1 in patients weighing ≥25kg;12,14 and treatment of HIV-1 in patients weighing ≥40kg.15

Associated Conditions
Pharmacodynamics

Emtricitabine is a cytidine analog that competes with the natural substrate of HIV-1 reverse transcriptase to be incorporated into newly formed DNA, terminating its transcription.5 It is administered once daily so it has a long duration of action. Patients should be counselled regarding the risk of lactic acidosis and hepatomegaly with steatosis.5

Mechanism of action

Emtricitabine is a cytidine analog which, when phosphorylated to emtricitabine 5'-triphosphate, competes with deoxycytidine 5'-triphosphate for HIV-1 reverse transcriptase.5 As HIV-1 reverse transcriptase incorporates emtricitabine into forming DNA strands, new nucleotides are unable to be incorporated, leading to viral DNA chain termination.5 Inhibition of reverse transcriptase prevents transcription of viral RNA into DNA, therefore the virus is unable to incorporate its DNA into host DNA and replicate using host cell machinery. This reduces viral load.3

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Emtricitabine reaches a Cmax of 1.8±0.7µg/mL with a Tmax of 1-2 hours, and has an AUC of 10±3.1µg*hr/mL.5 The bioavailability of emtricitabine capsules is 93% and the bioavailability of the oral solution is 75%.5 Taking emtricitabine with food decreases the Cmax by 29%.[L9019

Volume of distribution

The apparent central volume of distribution is 42.3L and the peripheral volume of distribution is 55.4L.2

Protein binding

Emtricitabine is <4% bound to plasma proteins,5 mainly serum albumin.[A19948]

Metabolism

Emtricitabine is approximately 86% unmetabolized.5 Approximately 9% of a dose is metabolized to 3'-sulfoxide diastereomers, 4% to the 2'-O-glucuronide, and a minor amount is converted to 5-fluorocytosine.1,5

Route of elimination

Emtricitabine is 86% recovered in the urine and 14% recovered in feces.5 13% of the dose is recovered in the urine as metabolites; 9% as 3'-sulfoxide diastereomers and 4% as 2'-O-glucuronide.5

Half life

The half life of emtricitabine is approximately 10 hours.5

Clearance

Emtricitabine has an apparent elimination rate of 15.1L/h.2 This rate is closely linked to creatinine clearance.2

Toxicity

The LD50 of emtricitabine is not readily available.[9019,L9818]

Symptoms of emtricitabine toxicity include hepatotoxicity with steatosis, as well as lactic acidosis.5 Treat overdose with symptomatic and supportive measures, including hemodialysis.5

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

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirEmtricitabine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibThe excretion of Abemaciclib can be decreased when combined with Emtricitabine.
AcarboseAcarbose may decrease the excretion rate of Emtricitabine which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Emtricitabine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Emtricitabine which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Emtricitabine which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Emtricitabine which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Emtricitabine which could result in a higher serum level.
AclidiniumEmtricitabine may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineEmtricitabine may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

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

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  • Severity
    Severity

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

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  • Evidence Level
    Evidence Level

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

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  • Action
    Action

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

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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

References

Synthesis Reference
US5538975
General References
  1. Shockcor JP, Wurm RM, Frick LW, Sanderson PN, Farrant RD, Sweatman BC, Lindon JC: Hplc-nmr identification of the human urinary metabolites of (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl] cytosine, a nucleoside analogue active against human immunodeficiency virus (HIV). Xenobiotica. 1996 Feb;26(2):189-99. doi: 10.3109/00498259609046699. [PubMed:8868002]
  2. Valade E, Treluyer JM, Bouazza N, Ghosn J, Foissac F, Benaboud S, Fauchet F, Viard JP, Urien S, Hirt D: Population pharmacokinetics of emtricitabine in HIV-1-infected adult patients. Antimicrob Agents Chemother. 2014;58(4):2256-61. doi: 10.1128/AAC.02058-13. Epub 2014 Feb 3. [PubMed:24492366]
  3. Orkin C, Llibre JM, Gallien S, Antinori A, Behrens G, Carr A: Nucleoside reverse transcriptase inhibitor-reducing strategies in HIV treatment: assessing the evidence. HIV Med. 2018 Jan;19(1):18-32. doi: 10.1111/hiv.12534. Epub 2017 Jul 24. [PubMed:28737291]
  4. FDA Press Announcements: FDA approves second drug to prevent HIV infection as part of ongoing efforts to end the HIV epidemic [Link]
  5. FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules [Link]
  6. FDA Approved Drug Products: Descovy (Emtricitabine and Tenofovir Alafenamide) Oral Tablets [Link]
  7. Cayman Chemicals: Emtricitabine MSDS [Link]
  8. FDA Approved Drug Products: Truvada (Emtricitabine and Tenofovir Disoproxil Fumarate) Oral Tablets [Link]
  9. FDA Approved Drug Products: Symtuza (Darunavir, Cobicistat, Emtricitabine, and Tenofovir Alafenamide) Oral Tablets [Link]
  10. FDA Approved Drug Products: Stribild (Elvitegravir, Cobicistat, Emtricitabine, Tenofovir Disoproxil Fumarate) Oral Tablets [Link]
  11. FDA Approved Drug Products: Odefsey (Emtricitabine, Rilpivirine, and Tenofovir Alafenamide) [Link]
  12. FDA Approved Drug Products: Genvoya (Elvitegravir, Cobicistat, Emtricitabine, and Tenofovir Alafenamide) Oral Tablets [Link]
  13. FDA Approved Drug Products: Complera (Emtricitabine, Rilpivirine, Tenofovir Disoproxil Fumarate) Oral Tablets [Link]
  14. FDA Approved Drug Products: Biktarvy (Bictegravir, Emtricitabine, and Tenofovir Alafenamide) Oral Tablets [Link]
  15. FDA Approved Drug Products: Atripla (Efavirenz, Emtricitabine, and Tenofovir Disoproxil Fumarate) oral tablets [Link]
External Links
Human Metabolome Database
HMDB0015017
KEGG Drug
D01199
KEGG Compound
C12599
PubChem Compound
60877
PubChem Substance
46507606
ChemSpider
54859
BindingDB
50107843
RxNav
276237
ChEBI
31536
ChEMBL
CHEMBL885
ZINC
ZINC000003629271
Therapeutic Targets Database
DAP001084
PharmGKB
PA10069
PDBe Ligand
ETV
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Emtricitabine
ATC Codes
J05AR19 — Emtricitabine, tenofovir alafenamide and rilpivirineJ05AR08 — Emtricitabine, tenofovir disoproxil and rilpivirineJ05AR17 — Emtricitabine and tenofovir alafenamideJ05AF09 — EmtricitabineJ05AR09 — Emtricitabine, tenofovir disoproxil, elvitegravir and cobicistatJ05AR20 — Emtricitabine, tenofovir alafenamide and bictegravirJ05AR06 — Emtricitabine, tenofovir disoproxil and efavirenzJ05AR03 — Tenofovir disoproxil and emtricitabineJ05AR22 — Emtricitabine, tenofovir alafenamide, darunavir and cobicistatJ05AR18 — Emtricitabine, tenofovir alafenamide, elvitegravir and cobicistat
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
0Active Not RecruitingOtherContraception / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
0CompletedBasic SciencePre-Exposure Prophylaxis1
0CompletedOtherHealthy Volunteers1
0CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
0Not Yet RecruitingOtherHuman Immunodeficiency Virus (HIV) Infections / Medication Adherence1
0RecruitingPreventionHIV Prevention1
1Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
1CompletedNot AvailableAcquired Immune Deficiency Syndrome (AIDS)1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections2
1CompletedBasic ScienceHIV Prevention1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
1CompletedBasic ScienceTuberculosis Infection1
1CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV) Infections2
1CompletedOtherHIV Prevention1
1CompletedOtherHIV-DDI1
1CompletedOtherHuman Immunodeficiency Virus (HIV) Infections1
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections4
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections8
1CompletedTreatmentInsulin Resistance1
1Not Yet RecruitingPreventionHuman Immunodeficiency Virus Type 1 (HIV-1) Infection / Pregnancy1
1RecruitingOtherHIV Prevention / Medication Adherence1
1RecruitingOtherHealthy Volunteers1
1RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
1RecruitingPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1RecruitingTreatmentHealthy Volunteers1
1RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1RecruitingTreatmentInsulin Resistance1
1, 2CompletedOtherPrEP Adherence Monitoring1
1, 2CompletedTreatmentAcute HIV Infection1
1, 2CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
1, 2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection / Pf Subclinical Parasitemia1
1, 2Not Yet RecruitingTreatmentAicardi Goutières Syndrome1
2Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
2Active Not RecruitingTreatmentCentral Nervous System / Human Immunodeficiency Virus Type 1 (HIV-1)1
2Active Not RecruitingTreatmentContraception / Human Immunodeficiency Virus (HIV) Infections1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2CompletedOtherHuman Immunodeficiency Virus (HIV) Infections1
2CompletedOtherHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2CompletedPreventionAmphetamine-Related Disorders / 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) Infections6
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy2
2CompletedTreatment2- HIV Infection1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections2
2CompletedTreatmentAntiretroviral Naive / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAntiretroviral Therapies / Human Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
2CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHepatitis B Chronic Infection4
2CompletedTreatmentHepatitis B Virus (HBV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections15
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1) Infection1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lymphoma, AIDS Related1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Progressive Multifocal Leukoencephalopathy1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)3
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection6
2Not Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
2Not Yet RecruitingTreatmentPrimary Biliary Cholangitis1
2RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections2
2RecruitingPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
2RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection2
2TerminatedTreatmentHBV / Human Immunodeficiency Virus (HIV) Infections1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2TerminatedTreatmentViral Hepatitis B1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
2WithdrawnPreventionHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2WithdrawnTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
2WithdrawnTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2, 3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2, 3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
2, 3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2, 3CompletedPreventionHIV Pre-exposure Prophylaxis During Breastfeeding1
2, 3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatment2- HIV Infection1
2, 3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentAcute HIV Infection1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1
2, 3RecruitingOtherHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
2, 3WithdrawnTreatmentSaquinavir/Ritonavir BID or Lopinavir/Ritonavir BID1
3Active Not RecruitingPreventionHIV Prevention1
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections / STI1
3Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections6
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection8
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus-type 1 Infection1
3Active Not RecruitingTreatmentPre-Exposure Prophylaxis of HIV-1 Infection1
3CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections5
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1) Infection1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections7
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1)1
3CompletedTreatmentHBV / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHIV Risk1
3CompletedTreatmentHepatitis B Chronic Infection2
3CompletedTreatmentHepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus Type 1 (HIV-1) Infection1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections31
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection17
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection / Kaposi s Sarcoma (KS)1
3CompletedTreatmentViral Hepatitis B1
3Not Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3Not Yet RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
3RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections / Stimulant Use / Substance Use Disorders (SUD)1
3RecruitingPreventionInfections, Coronavirus / Novel Coronavirus Infectious Disease (COVID-19)1
3RecruitingTreatmentHIV-1/HBV Co-Infection1
3RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3RecruitingTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
3RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection3
3SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentHepatitis B Chronic Infection / Human Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
3TerminatedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) Infections / Infection1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3WithdrawnPreventionBreastfeeding / Human Immunodeficiency Virus (HIV) Infections / Pregnancy1
3WithdrawnTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
4Active Not RecruitingOtherAdherence, Medication / HIV Prevention / Pre-Exposure Prophylaxis / Risk Behaviors1
4Active Not RecruitingOtherHuman Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingOtherPre-Exposure Prophylaxis / Transgender Persons1
4Active Not RecruitingPreventionAdherence1
4Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections / Syphilis1
4Active Not RecruitingPreventionHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
4Active Not RecruitingTreatmentChronic Infection With HIV1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections2
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Menopause / Osteoporosis1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Severe Immunosuppression1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection / Solid Organ Transplant1
4CompletedNot AvailableHealthy Volunteers2
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Proteinuria1
4CompletedNot AvailablePharmacokinetic Study in Healthy Volunteers1
4CompletedBasic ScienceHIV Prevention / Transgender Health1
4CompletedBasic ScienceHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedBasic ScienceHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4CompletedDiagnosticAIDS-Related Opportunistic Infections / Human Immunodeficiency Virus (HIV) Infections1
4CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV) Infections1
4CompletedOtherAdherence to Medication Regime1
4CompletedOtherAdherence, Medication / HIV Prevention / Pre-Exposure Prophylaxis / Risk Behaviors1
4CompletedOtherCoinfection, HIV / Hepatitis C Viral Infection1
4CompletedOtherHealthy Volunteers2
4CompletedOtherHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4CompletedPreventionAdherence, Medication / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Substance Use Disorders (SUD)1
4CompletedPreventionAdolescent Behaviors / Gender / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionHIV Nonoccupational Post-exposure Prophylaxis in Men Who Have Sex With Men1
4CompletedPreventionHIV Prevention1
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections12
4CompletedTreatment2- HIV Infection1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Sleep disorders and disturbances1
4CompletedTreatmentAcute HIV Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentCardiovascular Heart Disease / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentDyslipidemia / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHIV Associated Neurocognitive Disorders (HAND) / HIV-Associated neurocognitive disorder (HAND) / Neurocognitive Decline1
4CompletedTreatmentHIV Prevention / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHIV, Combination Therapy1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHepatitis C Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections35
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1) Infection1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi s Sarcoma (KS)1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B2
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)4
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection6
4Enrolling by InvitationPreventionHuman Immunodeficiency Virus (HIV) Infections / Sexually Transmitted Disease (STD)1
4Enrolling by InvitationPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4Not Yet RecruitingPreventionAlcohol Use, Unspecified / Sex Behavior / Substance Use1
4Not Yet RecruitingTreatmentCoronary Artery Disease / Human Immunodeficiency Virus (HIV) Infections1
4Not Yet RecruitingTreatmentFibrosis / Hepatitis B Chronic Infection1
4Not Yet RecruitingTreatmentHepatitis B Chronic Infection1
4Not Yet RecruitingTreatmentHepatitis B Chronic Infection / Pregnancy1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection2
4RecruitingBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingOtherDrug Use / Human Immunodeficiency Virus Type 1 (HIV-1) Infection1
4RecruitingPreventionART / Human Immunodeficiency Virus (HIV) Infections1
4RecruitingPreventionBone Demineralization1
4RecruitingPreventionHIV Prevention1
4RecruitingPreventionHIV, Prevention1
4RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingPreventionPrEP Adherence Monitoring1
4RecruitingSupportive CareHuman Immunodeficiency Virus (HIV) Infections1
4RecruitingTreatmentAcute HIV Infection1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentBone Diseases, Metabolic / Buprenorphine Dependence / Chronic Hepatitis C Virus (HCV) Infection / Co-Infection / HCV Coinfection / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Human Immunodeficiency Virus Type 1 (HIV-1) Infection / Intravenous Drug Usage / Methadone Dependence / Opioid Dependence / Substance Abuse1
4RecruitingTreatmentBone Loss1
4RecruitingTreatmentHIV Seropositivity1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Neurocognitive Dysfunction1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Renal Insufficiency,Chronic / Therapeutic Agent Toxicity1
4RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection3
4RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection / Viral Hepatitis B1
4TerminatedPreventionHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections4
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Osteopenia1
4Unknown StatusBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
4Unknown StatusPreventionHepatitis B Chronic Infection / Pregnancy1
4Unknown StatusTreatmentHepatitis B Chronic Infection1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections4
4WithdrawnTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
4WithdrawnTreatmentViral Hepatitis B1
Not AvailableActive Not RecruitingNot AvailableBone Diseases / Chronic Hepatitis B in HIV Patient / Kidney Injury1
Not AvailableActive Not RecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableActive Not RecruitingNot AvailableHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
Not AvailableActive Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableActive Not RecruitingTreatment2- HIV Infection1
Not AvailableCompletedNot AvailableHIV Seropositivity / Pregnancy, High-Risk1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections9
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
Not AvailableCompletedBasic ScienceHealthy Volunteers / Pharmacokinetics1
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedOtherHuman Immunodeficiency Virus (HIV) Infections / Sexually Transmitted Infections (STIs)1
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections9
Not AvailableCompletedPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableCompletedTreatmentAnti-Retroviral Agents / Dyslipidemia / Efavirenz / Human Immunodeficiency Virus Type 1 (HIV-1) Infection / Rilpivirine / Sustained Virologic Response1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections5
Not AvailableCompletedTreatmentPrimary Biliary Cholangitis1
Not AvailableEnrolling by InvitationNot AvailableHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableNot Yet RecruitingNot AvailableHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
Not AvailableNot Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableNot Yet RecruitingPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableNot Yet RecruitingPreventionHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
Not AvailableNot Yet RecruitingTreatmentHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableRecruitingNot AvailableHIV Chemoprophylaxis / HIV Preexposure Prophylaxis1
Not AvailableRecruitingNot AvailableHIV Prevention1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections / 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 AvailableRecruitingNot AvailableHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
Not AvailableRecruitingBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableRecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedPreventionHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableTerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
Not AvailableTerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusPreventionHuman Immunodeficiency Virus (HIV) Infections / Immune Reconstitution Inflammatory Syndrome1
Not AvailableWithdrawnNot AvailableHIV-infected Patients1
Not AvailableWithdrawnNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infertility1

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
CapsuleOral200 mg/1
SolutionOral10 mg/1mL
Tablet, film coatedOral
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)
US7402588No2008-07-222010-02-01Us
CA2075189No2004-11-302011-01-31Canada
US7800788No2010-09-212022-02-02Us
US5914331Yes1999-06-222018-01-02Us
US6043230Yes2000-03-282018-01-25Us
US5814639Yes1998-09-292017-03-29Us
US6939964Yes2005-09-062018-07-20Us
US6639071Yes2003-10-282018-08-14Us
US6642245Yes2003-11-042021-05-04Us
US6703396Yes2004-03-092021-09-09Us
US5922695Yes1999-07-132018-01-25Us
US5935946Yes1999-08-102018-01-25Us
US5977089Yes1999-11-022018-01-25Us
US8592397No2013-11-262024-01-13Us
US8716264No2014-05-062024-01-13Us
US9018192No2015-04-282026-06-13Us
US8598185No2013-12-032028-05-01Us
US7470506Yes2008-12-302019-12-23Us
US8597876Yes2013-12-032019-12-23Us
US7700645Yes2010-04-202027-06-26Us
US8518987Yes2013-08-272024-08-16Us
US7125879No2006-10-242022-08-09Us
US6838464No2005-01-042021-02-26Us
US8080551No2011-12-202023-04-11Us
US8101629No2012-01-242022-08-09Us
US7067522No2006-06-272019-12-20Us
US8148374No2012-04-032029-09-03Us
US7635704No2009-12-222026-10-26Us
US7176220No2007-02-132023-11-20Us
US8981103No2015-03-172026-10-26Us
US8633219No2014-01-212030-04-24Us
US8841310No2014-09-232025-12-09Us
US9296769No2016-03-292032-08-15Us
US7803788No2010-09-282022-02-02Us
US8754065No2014-06-172032-08-15Us
US7390791No2008-06-242022-05-07Us
US9545414No2017-01-172026-06-13Us
US9457036No2016-10-042024-01-13Us
US9744181No2017-08-292024-01-13Us
US9891239No2018-02-132029-09-03Us
US9889115Yes2018-02-132019-12-23Us
US9216996No2015-12-222033-12-19Us
US9708342No2017-07-182035-06-19Us
US9732092No2017-08-152033-12-19Us
US10039718No2018-08-072032-10-04Us
US10385067No2019-08-202035-06-19Us
US10548846No2016-11-082036-11-08Us
Additional Data Available
  • Filed On
    Filed On

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

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)136-138ChemSpider
boiling point (°C)443.28ChemSpider
water solubility112 mg/mLFDA Label
logP-0.43FDA Label
pKa2.65FDA Label
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]
  4. FDA Approved Drug Products: Emtriva (Emtricitabine) Oral Capsules [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based...
Gene Name
DCK
Uniprot ID
P27707
Uniprot Name
Deoxycytidine kinase
Molecular Weight
30518.315 Da
References
  1. 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
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. [PubMed:15814459]
  2. Bocedi A, Notari S, Menegatti E, Fanali G, Fasano M, Ascenzi P: Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. FEBS J. 2005 Dec;272(24):6287-96. [PubMed:16336266]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. Reznicek J, Ceckova M, Cerveny L, Muller F, Staud F: Emtricitabine is a substrate of MATE1 but not of OCT1, OCT2, P-gp, BCRP or MRP2 transporters. Xenobiotica. 2017 Jan;47(1):77-85. doi: 10.3109/00498254.2016.1158886. Epub 2016 Apr 6. [PubMed:27052107]

Drug created on June 13, 2005 07:24 / Updated on May 25, 2020 23:43

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