Emtricitabine

Emtricitabine (commonly called FTC, systematic name 2',3'-dideoxy-5-fluoro-3'-thiacytidine), with trade name Emtriva (formerly Coviracil), is a nucleoside reverse-transcriptase inhibitor (NRTI) for the prevention and treatment of HIV infection in adults and children. In 2019, it was the 494th most commonly prescribed medication in the United States, with more than 3 thousand prescriptions.

Emtricitabine
Clinical data
Pronunciation/ˌɛmtrəˈsaɪtəbiːn/
EM-trə-SY-tə-been
Trade namesEmtriva
Other namesFTC
AHFS/Drugs.comMonograph
MedlinePlusa604004
License data
Pregnancy
category
  • AU: B1
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability93%
Protein bindingVery low (less than 4%)
MetabolismHepatic oxidation and glucuronidation
CYP system not involved
Elimination half-life10 hours
ExcretionRenal (86%) and fecal (14%)
Identifiers
  • 4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.120.945
Chemical and physical data
FormulaC8H10FN3O3S
Molar mass247.24 g·mol−1
3D model (JSmol)
  • FC=1\C(=N/C(=O)N(C=1)[C@H]2O[C@H](SC2)CO)\N
  • 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 Y
  • Key:XQSPYNMVSIKCOC-NTSWFWBYSA-N Y
  (verify)

Emtricitabine makes up one fourth of the Quad pill (brand names: Stribild and Genvoya). It is also marketed in a fixed-dose combination with tenofovir disoproxil (Viread) under the brand name Truvada, and with tenofovir alafenamide (Vemlidy) under the brand name Descovy. In fixed-dose combinations with tenofovir or with efavirenz and tenofovir it is on the World Health Organization's List of Essential Medicines. A fixed-dose triple combination of emtricitabine, tenofovir and efavirenz (Sustiva, marketed by Bristol-Myers Squibb) was approved by the U.S. Food and Drug Administration (FDA) on July 12, 2006, under the brand name Atripla.

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