Emtricitabine (CED0002300)

Record Information
Version1.0
Creation Date2016-05-22 04:26:05 UTC
Update Date2026-08-24 10:48:22 UTC
Accession NumberCHEM017526
Identification
Common NameEmtricitabine
ClassSmall Molecule
Description
Emtricitabine is an organic compound with the formula C8H10FN3O3S and an average molecular weight of 247.25 g/mol. Emtricitabine belongs to the 3'-thia pyrimidine nucleosides, a subclass of nucleoside and nucleotide analogues within the organic compounds. This compound acts as an inhibitor or modulator of two recorded protein targets: the Gag-Pol polyprotein (gag-pol) and Reverse transcriptase/RNaseH (pol). The substance is found in or released from seven recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an antiviral. Other recorded sources include household cleaning and consumer products, specifically non electric simulated smoking devices, as well as electrical and electronic equipment, including television systems, video games, and electrically stimulated smoking devices. Additionally, it is associated with food, food processing, and cookware, specifically in the preparation of malt and the preparation of wine or sparkling wine. The recorded exposure route for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(2R,5S)-5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosineChEBI
(-)-2'-Deoxy-5-fluoro-3'-thiacytidineChEBI
(-)-beta-2',3'-Dideoxy-5-fluoro-3'-thiacytidineChEBI
(-)-cis-4-Amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-oneChEBI
(-)-FTCChEBI
(2R-cis)-4-Amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinoneChEBI
4-Amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-oneChEBI
4-Amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1H-pyrimidin-2-oneChEBI
5-Fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosineChEBI
EmtrivaKegg
ABBR FTCKegg
(-)-b-2',3'-Dideoxy-5-fluoro-3'-thiacytidineGenerator
(-)-Β-2',3'-dideoxy-5-fluoro-3'-thiacytidineGenerator
(-)-2',3'-Dideoxy-5-fluoro-3'-thiacytidineHMDB
(-)-EmtricitabineHMDB
CoviracilHMDB
EmtricitabineHMDB
Beta L 2',3' Dideoxy 5 fluoro 3' thiacytidineMeSH
beta-L-2',3'-Dideoxy-5-fluoro-3'-thiacytidineMeSH
Chemical FormulaC8H10FN3O3S
Average Molecular Mass247.247 g/mol
Monoisotopic Mass247.043 g/mol
CAS Registry Number143491-57-0
IUPAC Name4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
Traditional Nameemtricitabine
SMILESNC1=NC(=O)N(C=C1F)[C@@H]1CS[C@H](CO)O1
InChI IdentifierInChI=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
InChI KeyXQSPYNMVSIKCOC-NTSWFWBYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassNucleoside and nucleotide analogues
Sub Class3'-thia pyrimidine nucleosides
Direct Parent3'-thia pyrimidine nucleosides
Alternative Parents
Substituents
  • 3'-thia pyrimidine nucleoside
  • Aminopyrimidine
  • Halopyrimidine
  • Pyrimidone
  • Aryl fluoride
  • Aryl halide
  • Hydropyrimidine
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Monothioacetal
  • Oxathiolane
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Primary amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.37 m³·mol⁻¹ChemAxon
Polarizability21.79 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-005c-9840000000-916eed674e8dde443d6eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fep-8292000000-b2dcf9a13b9a869927ccNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-70cf3fd58a0517da4a55Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-94b3e0720e27e6745a1fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-8dbfc14b46cc1f58e910Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-2dad282fe8707980881dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-efef9ecafd739446f7aeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-349c2005cbcd9008b160Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-6dae6d5531a8a2f408cdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-b8b0b2a41b04924a3ae6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-b0b20b1959137a52d9c7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-bd2c9f863694963a9078Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1900000000-9903921aee7742b373e7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1900000000-8857a02a53df79efbd5cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-961f6f9132af62bc5e1eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-09ba1f683ca6a306fa48Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-85e4574e24a912428e0dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-98f516d8a1dfac9bd187Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-d38aba7b54ffd5599634Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-77bf43e48b391e0cc9e6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-f3f824943162b24c1e4fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-44a806bdaafeab648de7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1900000000-1d372de7c237ff942cc0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1900000000-5d95350be120eba447d0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-7ef4730432ae6d2c0e9fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-74ecfe9c417f5d317774Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0920000000-810d7a7def89643865a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1900000000-009baab415006b7bc307Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-6900000000-4ee98d10e3447b6c66acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-2390000000-77ee7291923983e61f8bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ukl-1910000000-fa4bf50b1d66f4072746Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9100000000-634ee8be27db1e259199Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0930000000-ce2b917733559b8162a2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-1900000000-696cae5904cfdeb27073Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-7900000000-f65c3a2941bd7a2fad8dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0390000000-ba38a2da98891262db90Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1900000000-e85cf296120f08c41760Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-fa3634c67140b1b723ceNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1064.0Log mg/kg[600:1900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
351AntiviralsHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Emtricitabine Action Pathway
Emtricitabine Action Pathway
Emtricitabine Drug Metabolism Action Pathway
Emtricitabine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)17.2047
Click to view 3D structureHeat shock factor protein 1P38532Mus musculusPredicted (SEA)104.396
Click to view 3D structureCore antigenQ03732Hepatitis B virusPredicted (SEA)0.856341
Genome polyprotein structureClick to view 3D structureGenome polyproteinP03300Poliovirus type 1 (strain Mahoney)Predicted (SEA)15.2584
Click to view 3D structureThymidylate synthase ThyAP9WFR9Mycobacterium tuberculosisPredicted (SEA)6.15009
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)1266.14
Thymidine kinase, cytosolic structureClick to view 3D structureThymidine kinase, cytosolicP04183HumansPredicted (SEA)5.68299
Click to view 3D structureAdenosine kinaseA5U4N0Mycobacterium tuberculosis (strain ATCC 25177 / H37Ra)Predicted (SEA)39.4696
Thymidine kinase structureClick to view 3D structureThymidine kinaseP0C0E6HHV-3Predicted (SEA)17.8275
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)729.214
Calmodulin-like protein 3 structureClick to view 3D structureCalmodulin-like protein 3P27482HumansPredicted (SEA)21.7978
Adenosine kinase structureClick to view 3D structureAdenosine kinaseP55263HumansPredicted (SEA)121.756
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)890.673
Click to view 3D structureThymidine kinaseP06479Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1)Predicted (SEA)8.79696
Tyrosine--tRNA ligase structureClick to view 3D structureTyrosine--tRNA ligaseP0AGJ9Escherichia coli (strain K12)Predicted (SEA)34.7986
DNA (cytosine-5)-methyltransferase 1 structureClick to view 3D structureDNA (cytosine-5)-methyltransferase 1P26358HumansPredicted (SEA)815.471
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)2148.48
DNA polymerase beta structureClick to view 3D structureDNA polymerase betaP06746HumansPredicted (SEA)17.4382
Click to view 3D structureThymidine kinaseP09250HHV-3Predicted (SEA)17.5161
Click to view 3D structureAdenosine receptor A3P28647Rattus norvegicusPredicted (SEA)358.106
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)2478.56
Click to view 3D structureThymidine kinase 2D3ZGQ2Rattus norvegicusPredicted (SEA)54.8059
DNA polymerase subunit gamma-1 structureClick to view 3D structureDNA polymerase subunit gamma-1P54098HumansPredicted (SEA)12.1445
CD99 antigen structureClick to view 3D structureCD99 antigenP14209HumansPredicted (SEA)58.7762
Heat shock protein HSP 90-alpha structureClick to view 3D structureHeat shock protein HSP 90-alphaP07900HumansPredicted (SEA)1183.7
Concentrations
Not Available
External Links
DrugBank IDDB00879
HMDB IDHMDB0015017
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEmtricitabine
Chemspider ID54859
ChEBI ID31536
PubChem Compound ID60877
Kegg Compound IDC12599
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11491420
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14609348
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14693538
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15206508
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15249567
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15588339
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15875341
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15977972
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16034488
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16323102
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16401810
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17526857
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19493710
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22915463
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22917277
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22935078
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23337366
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23361642
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682
20. Authors unspecified: Emtricitabine/tenofovir disoproxil fumarate. Drugs R D. 2004;5(3):160-1.
21. 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.
22. Masho SW, Wang CL, Nixon DE: Review of tenofovir-emtricitabine. Ther Clin Risk Manag. 2007 Dec;3(6):1097-104.
23. Long MC, King JR, Acosta EP: Pharmacologic aspects of new antiretroviral drugs. Curr HIV/AIDS Rep. 2009 Feb;6(1):43-50.