Chemical Component Summary

Name4-AMINO-5-FLUORO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]PYRIMIDIN-2(1H)-ONE
Synonyms5-FLUORO-(-)-L-2',3'-DIDEOXY-3'-THIACYTIDINE; (-)-BETA-2',3'-DIDEOXY-5-FLUORO-3'-THIACYTIDINE; EMTRICITABINE; EMTRIVA
Identifiers4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
FormulaC8 H10 F N3 O3 S
Molecular Weight247.247
TypeNON-POLYMER
Isomeric SMILESC1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F
InChIInChI=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
InChIKeyXQSPYNMVSIKCOC-NTSWFWBYSA-N

Chemical Details

Formal Charge0
Atom Count26
Chiral Atom Count2
Bond Count27
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00879 
NameEmtricitabine
Groups
  • approved
  • investigational
DescriptionEmtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) indicated for the treatment of HIV infection in adults[L9019] or combined with [tenofovir alafenamide] for the prevention of HIV-1 infection in high risk adolescents and adults.[L9010] Emtricitabine is a cytidine analogue.[L9019] The drug works by inhibiting HIV reverse transcriptase, preventing transcription of HIV RNA to DNA.[L9019] Emtricitabine was granted FDA approval on 2 July 2003.[L9019]
Synonyms
  • (−)-FTC
  • Emtricitabinum
  • (−)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • Emtricitabina
  • 4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one
Brand Names
  • PMS-emtricitabine-tenofovir
  • Stribild
  • Symtuza
  • Emtricitabine/tenofovir Disoproxil Zentiva
  • Mylan-emtricitabine/tenofovir Disoproxil
IndicationEmtricitabine is indicated in combination with other medications for the treatment of HIV-1 infections;[L9019,L9836,L44226] 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;[L4388,L9010] treatment of HIV-1 infections in pediatric and adult patients ≥17kg, pre exposure prophylaxis in adolescents and adults ≥35kg;[L9833] treatment of HIV-1 in patients ≥12 years and ≥35kg;[L9587] treatment of HIV-1 in patients weighing ≥35kg;[L9839,L9842] treatment of HIV-1 in patients weighing ≥25kg;[L9647,L9845] and treatment of HIV-1 in patients weighing ≥40kg.[L9848]
Categories
  • Anti-HIV Agents
  • Anti-Infective Agents
  • Anti-Retroviral Agents
  • Antiinfectives for Systemic Use
  • Antiviral Agents
ATC-Code
  • J05AR19
  • J05AR08
  • J05AR17
  • J05AF09
  • J05AR09
CAS number143491-57-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Reverse transcriptase/RNaseHPISPIETVPVKLKPGMDGPKVKQWPLTEEKIKALVEICTEMEKEGKISKI...unknowninhibitor
Deoxycytidine kinaseMATPPKRSCPSFSASSEGTRIKKISIEGNIAAGKSTFVNILKQLCEDWEV...unknownsubstrate
Serum albuminMKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...unknownbinder
Multidrug and toxin extrusion protein 1MEAPEEPAPVRGGPEATLEVRGSRCLRLSAFREELRALLVLAGPAFLVQL...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 60877
ChEMBL CHEMBL885
ChEBI CHEBI:31536
CCDC/CSD DUQZAT, TUVNEG, TUVLOO, OMACAJ, DUQZIB