ETV

4-AMINO-5-FLUORO-1-[(2R,5S)-2-(HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]PYRIMIDIN-2(1H)-ONE

Created: 2006-10-26
Last modified:  2020-06-05

Find related ligands:

Chemical Details

Formal Charge0
Atom Count26
Chiral Atom Count2
Bond Count27
Aromatic Bond Count6
2D diagram of ETV

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
Systematic Name (OpenEye OEToolkits)4-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

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04FC=1C(=NC(=O)N(C=1)C2OC(SC2)CO)N
SMILESCACTVS3.341NC1=NC(=O)N(C=C1F)[CH]2CS[CH](CO)O2
SMILESOpenEye OEToolkits1.5.0C1C(OC(S1)CO)N2C=C(C(=NC2=O)N)F
Canonical SMILESCACTVS3.341 NC1=NC(=O)N(C=C1F)[C@@H]2CS[C@H](CO)O2
Canonical SMILESOpenEye OEToolkits1.5.0 C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F
InChIInChI1.03 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
InChIKeyInChI1.03 XQSPYNMVSIKCOC-NTSWFWBYSA-N

Drug Info: DrugBank

DrugBank IDDB00879 
NameEmtricitabine
Groups
  • investigational
  • approved
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
  • (−)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
  • (−)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one
  • (−)-2'-deoxy-5-fluoro-3'-thiacytidine
  • Emtricitabin
  • Emtricitabina
Brand Names
  • PMS-efavirenz-emtricitabine-tenofovir
  • Stribild Access
  • Auro-efavirenz-emtricitabine-tenofovir
  • Symtuza
  • COMPLERA Access
IndicationEmtricitabine is indicated in combination with other medications for the treatment of HIV-1 infections in adults and children.[L9019,L9587,L9836,L9833,L9839,L9842,L9647,L9845,L9848,L44226,L50522] As different products of emtricitabine are approved for use in patients with certain characteristics, refer to the individual drug product for patient eligibility for drug treatment. It may be used for pre-exposure prophylaxis of HIV-1 in adolescents and adults.[L4388,L9010]
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
Gag-Pol polyproteinMGARASVLSGGELDRWEKIRLRPGGKKKYKLKHIVWASRELERFAVNPGL...unknownmodulator
Deoxycytidine kinaseMATPPKRSCPSFSASSEGTRIKKISIEGNIAAGKSTFVNILKQLCEDWEV...unknownsubstrate
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