Emtricitabine

Emtricitabine
Clinical data
Pronunciation	/ˌɛmtrɪˈsaɪtəbiːn/; EM-tri-SY-tə-been
Trade names	Emtriva
Other names	FTC
AHFS/Drugs.com	Monograph
MedlinePlus	a604004
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: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	93%
Protein binding	Very low (less than 4%)
Metabolism	Hepatic oxidation and glucuronidation; CYP system not involved
Elimination half-life	10 hours
Excretion	Renal (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 ;
PubChem CID	60877;
DrugBank	DB00879 ;
ChemSpider	54859 ;
UNII	G70B4ETF4S;
KEGG	D01199 ;
ChEBI	CHEBI:31536 ;
ChEMBL	ChEMBL885 ;
NIAID ChemDB	004782;
CompTox Dashboard (EPA)	DTXSID0040129 ;
ECHA InfoCard	100.120.945
Chemical and physical data
Formula	C8H10FN3O3S
Molar mass	247.24 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 ; Key:XQSPYNMVSIKCOC-NTSWFWBYSA-N ;
	(verify)

Emtricitabine (commonly called FTC, systematic name 2',3'-dideoxy-5-fluoro-3'-thiacytidine^[1]), 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.^[2]

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.^[3] 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.

^ 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
^ "Emtricitabine - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 7 October 2022.
^ 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.

[1] 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

[2] "Emtricitabine - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 7 October 2022.

[WHO21st-3] 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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