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Emtricitabine information


Emtricitabine
Clinical data
Pronunciation/ˌɛmtrəˈstəbn/
EM-trə-SY-tə-been
Trade namesEmtriva
Other namesFTC
AHFS/Drugs.comMonograph
MedlinePlusa604004
License data
  • EU EMA: by INN
  • US DailyMed: Emtricitabine
Pregnancy
category
  • AU: B1
Routes of
administration
By mouth
ATC code
  • J05AF09 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: WARNING[1]Rx-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
IUPAC name
  • 4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
CAS Number
  • 143491-57-0 checkY
PubChem CID
  • 60877
DrugBank
  • DB00879 checkY
ChemSpider
  • 54859 checkY
UNII
  • G70B4ETF4S
KEGG
  • D01199 checkY
ChEBI
  • CHEBI:31536 checkY
ChEMBL
  • ChEMBL885 checkY
NIAID ChemDB
  • 004782
CompTox Dashboard (EPA)
  • DTXSID0040129 Edit this at Wikidata
ECHA InfoCard100.120.945 Edit this at Wikidata
Chemical and physical data
FormulaC8H10FN3O3S
Molar mass247.24 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • FC=1\C(=N/C(=O)N(C=1)[C@H]2O[C@H](SC2)CO)\N
InChI
  • 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 checkY
  • Key:XQSPYNMVSIKCOC-NTSWFWBYSA-N checkY
  (verify)

Emtricitabine (commonly called FTC, systematic name 2',3'-dideoxy-5-fluoro-3'-thiacytidine[2]), 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.[3]

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.[4] 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.

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ US 5814639, Liotta DC, Schinazi RF, Choi WB, "Method for the synthesis, compositions and use of 2'-deoxy-5-fluoro-3'-thiacytidine and related compounds", issued 29 September 1998, assigned to Emory University  Archived 31 May 2021 at the Wayback Machine
  3. ^ "Emtricitabine - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 7 October 2022.
  4. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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Emtricitabine

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Emtricitabine (commonly called FTC, systematic name 2',3'-dideoxy-5-fluoro-3'-thiacytidine), with trade name Emtriva (formerly Coviracil), is a nucleoside...

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Tenofovir alafenamide

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in November 2015 (compare elvitegravir/cobicistat/emtricitabine/tenofovir; (Stribild)) Emtricitabine/rilpivirine/tenofovir alafenamide (Odefsey) — approved...

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Tenofovir disoproxil

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in combinations such as emtricitabine/tenofovir, efavirenz/emtricitabine/tenofovir, and elvitegravir/cobicistat/emtricitabine/tenofovir. It does not cure...

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Cabotegravir

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long-acting pre-exposure prophylaxis (PrEP) with greater efficacy than the emtricitabine/tenofovir combination being widely used for PrEP at the time. The safety...

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Integrase inhibitor

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of the fixed dose combination with emtricitabine and tenofovir disoproxil (elvitegravir/cobicistat/emtricitabine/tenofovir). Elvitegravir is a low-molecular-weight...

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ATC code J05

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Abacavir J05AF07 Tenofovir disoproxil J05AF08 Adefovir dipivoxil J05AF09 Emtricitabine J05AF10 Entecavir J05AF11 Telbivudine J05AF12 Clevudine J05AF13 Tenofovir...

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Bictegravir

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alafenamide (TAF) and emtricitabine (FTC) for the treatment of HIV-1 infection. The combination drug bictegravir/emtricitabine/tenofovir alafenamide (Biktarvy)...

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Rilpivirine

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as metabolites. A fixed-dose medication combining rilpivirine with emtricitabine and tenofovir disoproxil (TDF) was approved by the U.S. Food and Drug...

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WHO Model List of Essential Medicines

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Efavirenz/emtricitabine/tenofovir Efavirenz/lamivudine/tenofovir (efavirenz + lamivudine + tenofovir) Emtricitabine/tenofovir (emtricitabine + tenofovir)...

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Gilead Sciences

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acquire Triangle for around $464 million; Triangle's lead drug was emtricitabine that was near FDA approval, and it had two other antivirals in its pipeline...

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List of antiviral drugs

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Atazanavir HIV PI Atripla (Efavirenz/emtricitabine/tenofovir) HIV Efavirenz: Non-nucleoside RTI (NNRTI) Emtricitabine: NRTI Tenofovir disoproxil: NRTI Baloxavir...

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Cobicistat

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fixed-dose combination HIV treatments. The first, elvitegravir/cobicistat/emtricitabine/tenofovir disoproxil, is marketed as Stribild and was approved by the...

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Darunavir

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and in the fixed-dose combination medication darunavir/cobicistat/emtricitabine/tenofovir alafenamide (Symtuza). Darunavir is indicated for the treatment...

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Efavirenz

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exposure. It is sold both by itself and in combination as efavirenz/emtricitabine/tenofovir. It is taken by mouth. Common side effects include rash, nausea...

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FTC

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United Kingdom Fashion Television Channel, a Canadian television channel Emtricitabine, an antiretroviral drug used to treat HIV, coded FTC in medical journals...

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