Identification

Name
Emtricitabine
Accession Number
DB00879
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

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 247.247
Monoisotopic: 247.042690096
Chemical Formula
C8H10FN3O3S
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

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
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
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

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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

Adverse Effects
Learn about our commercial Adverse Effects data.
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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.
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  • Evidence Level
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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Images
International/Other Brands
Coviracil
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EmtrivaCapsule200 mg/1OralRemedy Repack2008-05-172017-04-28US flag
EmtrivaCapsule200 mg/1OralExcella Gmb H2003-07-02Not applicableUS flag
EmtrivaSolution10 mg/1mLOralGilead Sciences, Inc.2005-09-28Not applicableUS flag
EmtrivaCapsule200 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUS flag
EmtrivaCapsule200 mg/1OralGilead Sciences, Inc.2003-07-02Not applicableUS flag
EmtrivaCapsule200 mg/1OralPhysicians Total Care, Inc.2003-07-10Not applicableUS flag
EmtrivaCapsule200 mgOralGilead Sciences2006-03-03Not applicableCanada flag
EmtrivaCapsule200 mg/1OralREMEDYREPACK INC.2019-02-04Not applicableUS flag
OdefseyTablet, film coatedOralGilead Sciences Ireland Uc2016-06-21Not applicableEU flag
OdefseyTablet, film coatedOralGilead Sciences Ireland Uc2016-06-21Not applicableEU flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    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
    Available for Purchase

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EmtricitabineCapsule200 mg/1OralREMEDYREPACK INC.2020-10-12Not applicableUS flag
EmtricitabineCapsule200 mg/1OralCipla USA Inc.2020-08-31Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    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
    Available for Purchase

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ag-emtricitabine / Tenofovir Disoproxil FumarateEmtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Apo-efavirenz-emtricitabine-tenofovirEmtricitabine (200 mg) + Efavirenz (600 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralApotex Corporation2018-09-04Not applicableCanada flag
Apo-emtricitabine-tenofovirEmtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralApotex Corporation2017-07-26Not applicableCanada flag
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 flag
AtriplaEmtricitabine (200 mg) + Efavirenz (600 mg) + Tenofovir disoproxil fumarate (300 mg)TabletOralGilead Sciences, Llc2007-10-23Not applicableCanada flag
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-20Not applicableUS flag
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralAvera McKennan Hospital2015-03-062017-05-24US flag
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-202019-11-30US flag
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralREMEDYREPACK INC.2017-03-20Not applicableUS flag
AtriplaEmtricitabine (200 mg/1) + Efavirenz (600 mg/1) + Tenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralDoh Central Pharmacy2009-07-01Not applicableUS flag

Categories

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
Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / Alcohol / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Halopyrimidine / Heteroaromatic compound
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, pyrimidone, nucleoside analogue, monothioacetal (CHEBI:31536)

Chemical Identifiers

UNII
G70B4ETF4S
CAS number
143491-57-0
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)[[email protected]@H]1CS[[email protected]](CO)O1

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]
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
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
4Active Not RecruitingOtherAdherence, Medication / HIV Prevention / Pre-Exposure Prophylaxis / Risk Behaviors1
4Active Not RecruitingOtherHealthy Volunteers1
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 RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Menopause / Osteoporosis1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection / Solid Organ Transplant1
4CompletedNot AvailableHealthy Volunteers2

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
Tablet, film coatedOral600 mg
Tablet, film coatedOral50 MG
Tablet, coatedOral50 mg
Tablet, film coatedOral10 mg
Tablet, coatedOral200 mg
Tablet, film coatedOral245 mg
Tablet, film coatedOral200 mg
CapsuleOral200 MG
CapsuleOral200 mg/1
SolutionOral10 mg/ml
SolutionOral10 mg/1mL
Tablet, coatedOral600 mg
Tablet, film coatedOral150 MG
Tablet, coatedOral150 mg
TabletOral
TabletOral200 MG
Tablet, film coatedOral
Tablet, film coatedOral800 MG
Tablet, film coatedOral300 mg
Tablet, film coatedOral
Tablet, film coatedOral200 mg/1
TabletOral300 mg
TabletOral600 mg
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)Region
US7402588No2008-07-222010-02-01US flag
CA2075189No2004-11-302011-01-31Canada flag
US7800788No2010-09-212022-02-02US flag
US5914331Yes1999-06-222018-01-02US flag
US6043230Yes2000-03-282018-01-25US flag
US5814639Yes1998-09-292017-03-29US flag
US6939964Yes2005-09-062018-07-20US flag
US6639071Yes2003-10-282018-08-14US flag
US6642245Yes2003-11-042021-05-04US flag
US6703396Yes2004-03-092021-09-09US flag
US5922695Yes1999-07-132018-01-25US flag
US5935946Yes1999-08-102018-01-25US flag
US5977089Yes1999-11-022018-01-25US flag
US8592397No2013-11-262024-01-13US flag
US8716264No2014-05-062024-01-13US flag
US9018192No2015-04-282026-06-13US flag
US8598185No2013-12-032028-05-01US flag
US7470506Yes2008-12-302019-12-23US flag
US8597876Yes2013-12-032019-12-23US flag
US7700645Yes2010-04-202027-06-26US flag
US8518987Yes2013-08-272024-08-16US flag
US7125879No2006-10-242022-08-09US flag
US6838464No2005-01-042021-02-26US flag
US8080551No2011-12-202023-04-11US flag
US8101629No2012-01-242022-08-09US flag
US7067522No2006-06-272019-12-20US flag
US8148374No2012-04-032029-09-03US flag
US7635704No2009-12-222026-10-26US flag
US7176220No2007-02-132023-11-20US flag
US8981103No2015-03-172026-10-26US flag
US8633219No2014-01-212030-04-24US flag
US8841310No2014-09-232025-12-09US flag
US9296769No2016-03-292032-08-15US flag
US7803788No2010-09-282022-02-02US flag
US8754065No2014-06-172032-08-15US flag
US7390791No2008-06-242022-05-07US flag
US9545414No2017-01-172026-06-13US flag
US9457036No2016-10-042024-01-13US flag
US9744181No2017-08-292024-01-13US flag
US9891239No2018-02-132029-09-03US flag
US9889115Yes2018-02-132019-12-23US flag
US9216996No2015-12-222033-12-19US flag
US9708342No2017-07-182035-06-19US flag
US9732092No2017-08-152033-12-19US flag
US10039718No2018-08-072032-10-04US flag
US10385067No2019-08-202035-06-19US flag
US10548846No2016-11-082036-11-08US flag
US10786515No2018-07-192038-07-19US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

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

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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

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 November 30, 2020 13:38

Cs molecular health 1