Emtricitabine

Emtricitabine

Clinical data
Trade names	Emtriva
AHFS/Drugs.com	Monograph
MedlinePlus	a604004
Pregnancy category	AU: B1 US: B (No risk in non-human studies)
Routes of administration	Oral
ATC code	J05AF09 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	93%
Protein binding	Very low (less than 4%)
Metabolism	Hepatic oxidation and glucuronidation system not involved
Biological 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]-1,2-dihydropyrimidin-2-one
CAS Number	143491-57-0 Y
PubChem CID	60877
DrugBank	DB00879 Y
ChemSpider	54859 Y
UNII	G70B4ETF4S
KEGG	D01199 Y
ChEBI	CHEBI:31536 Y
ChEMBL	CHEMBL885 Y
NIAID ChemDB	004782
ECHA InfoCard	100.120.945
Chemical and physical data
Formula	C8H10FN3O3S
Molar mass	247.248 g/mol
3D model (Jmol)	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 Y Key:XQSPYNMVSIKCOC-NTSWFWBYSA-N Y

Emtricitabine (2'-deoxy-5-fluoro-3'thiacytidine,FTC), with trade name Emtriva (formerly Coviracil), is a nucleoside reverse transcriptase inhibitor (NRTI) for the treatment of HIV infection in adults and children.

Emtricitabine is also marketed in a fixed-dose combination with tenofovir (Viread) under the brand name Truvada.

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.

Emtricitabine makes up one fourth of the Quad pill (brand name: Stribild).

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.

Emtricitabine is indicated in combination with other antiretroviral agents for the treatment of HIV infection in adults. Emtricitabine is commercially available and is approved by the FDA for treatment of HIV infection.

Emtricitabine exhibits clinical activity against the hepatitis B virus (HBV), but is not approved by the FDA for the treatment of HBV infection. Among individuals with chronic HBV infection, emtricitabine treatment results in significant histologic, virologic, and biochemical improvement. The safety profile of emtricitabine during treatment is similar to that of a placebo. Emtricitabine, like all other FDA approved drugs, cures neither HIV nor HBV infection. In a study involving individuals with HBV infection, symptoms of infection returned in 23% of emtricitabine-treated individuals who were taken off therapy. In studies involving individuals with chronic HIV infection, viral replication also resumes when study subjects are taken off therapy. As with drugs used to treat HIV infection, drugs used to treat HBV infection may have to be used in combination to prevent the evolution of drug resistant strains. The effectiveness of emtricitabine in combination with other anti-HBV drugs has not been established.