Structure via PubChem · Public domain (PubChem)
emtricitabine
Sign in to saveAlso known as BW-524W91, 524W91, 2'-deoxy-5-fluoro-3'thiacytidine, Coviracil, Emtriva, FTC, (−)-β-2',3'-dideoxy-5-fluoro-3'-thiacytidine, Emtricitabinum
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 3thousand prescriptions. It is an analog of the nucleoside cytidine.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 461093388
- Drug.image
- Emtricitabine structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 155
- Drug.caption
- Above: molecular structure of emtricitabine Below: 3D representation of an emtricitabine molecule
- Drug.image2
- Emtricitabine 3D.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Emtriva
- Drug.MedlinePlus
- a604004
- Drug.licence_EU
- yes
- Drug.DailyMedID
- Emtricitabine
- Drug.pregnancy_AU
- B1
- Drug.pregnancy_US
- B
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- J05
- Drug.ATC_suffix
- AF09
- Drug.legal_UK
- POM
via Wikipedia infobox
Chemical data
- Formula
- C8H10FN3O3S
- Molecular weight
- 247.25 g/mol
- IUPAC name
- 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
- SMILES
- C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F
- InChIKey
- XQSPYNMVSIKCOC-NTSWFWBYSA-N
- XLogP
- -0.6
- Polar surface area
- 113 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
4,453 papers- Emtricitabine and tenofovir alafenamide vs emtricitabine and tenofovir disoproxil fumarate for HIV pre-exposure prophylaxis (DISCOVER): primary results from a randomised, double-blind, multicentre, active-controlled, phase 3, non-inferiority trial.Lancet (London, England) · 2020
- Fixed-dose combination bictegravir, emtricitabine, and tenofovir alafenamide versus dolutegravir-containing regimens for initial treatment of HIV-1 infection: week 144 results from two randomised, double-blind, multicentre, phase 3, non-inferiority trials.The lancet. HIV · 2020
- Emtricitabine.Profiles of drug substances, excipients, and related methodology · 2020
- Long-term safety and efficacy of emtricitabine and tenofovir alafenamide vs emtricitabine and tenofovir disoproxil fumarate for HIV-1 pre-exposure prophylaxis: week 96 results from a randomised, double-blind, placebo-controlled, phase 3 trial.The lancet. HIV · 2021
- Bictegravir, emtricitabine, and tenofovir alafenamide versus dolutegravir, abacavir, and lamivudine for initial treatment of HIV-1 infection (GS-US-380-1489): a double-blind, multicentre, phase 3, randomised controlled non-inferiority trial.Lancet (London, England) · 2017
via PubMed
~4 min read
Encyclopedic overview
8 sectionsContents
- Medical uses
- HIV infection
- HBV infection
- Side effects
- Mechanism of action
- History
- References
- External links
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 3thousand prescriptions. It is an analog of the nucleoside cytidine.
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.
Excerpted from Wikipedia’s “emtricitabine” article, available under the CC BY-SA 4.0 licence.