Emtricitabine
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Systematic (IUPAC) name | |
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4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one | |
Clinical data | |
Pregnancy category | |
Routes of administration | Oral |
Legal status | |
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Pharmacokinetic data | |
Bioavailability | 93% |
Protein binding | Very low (less than 4%) |
Metabolism |
Hepatic oxidation and glucuronidation CYP system not involved |
Biological half-life | 10 hours |
Excretion | Renal (86%) and fecal (14%) |
Identifiers | |
CAS Number | 143491-57-0 |
ATC code | J05AF09 (WHO) |
PubChem | CID 60877 |
DrugBank | APRD00226 |
ChemSpider | 54859 |
Chemical data | |
Formula | C8H10FN3O3S |
Molar mass | 247.248 g/mol[[Script error: No such module "String".]] |
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Emtricitabine (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.
History
Emtricitabine was discovered by Dr. Dennis C. Liotta, Dr. Raymond Schinazi and Dr. Woo-Baeg Choi of Emory University and licensed to Triangle Pharmaceuticals by Emory in 1996.[1] Triangle Pharmaceuticals was acquired in 2003 by Gilead Sciences, who completed development and now market the product with the brand name Emtriva.
It was approved by the FDA July 2, 2003. It is very similar to 3TC and cross-resistance between the two is near-universal.
Mode of action
Emtricitabine is an analogue of cytidine. The drug works by inhibiting reverse transcriptase, the enzyme that copies HIV RNA into new viral DNA. By interfering with this process, which is central to the replication of HIV, emtricitabine can help to lower the amount of HIV, or "viral load", in a patient's body and can indirectly increase the number of immune system cells (called T cells or CD4+ T-cells). Both of these changes are associated with healthier immune systems and decreased likelihood of serious illness.
Indications
Emtricitabine is indicated in combination with other antiretroviral agents for the treatment of HIV infection in adults. This indication is based on the analyses of plasma HIV RNA levels and CD4 cell counts in two Phase III clinical trials of Emtriva of 48 weeks duration.
It is not indicated for the treatment of chronic hepatitis B virus infection and the safety and efficacy of emtricitabine have not been established in patients co-infected with HBV and HIV. Severe acute exacerbations of hepatitis B have been reported in patients after the discontinuation of emtricitabine. The drug is however being evaluated as a potential treatment for chronic hepatitis B. These studies are ongoing.
Side effects
In clinical practice, toxicity with emtricitabine is unusual. The most common treatment-related adverse events are diarrhea, headache, nausea, and rash. These symptoms are generally mild to moderate in severity, but they caused 1% of clinical trial patients to give up treatment. Skin discoloration, which is typically reported as hyperpigmentation and usually affects either the palms of the hands or the soles of the feet, is reported in less than 2% of individuals and is almost exclusive to patients of African origin.
Among the more severe side effects patients may experience are a hepatotoxicity or a lactic acidosis.
References
External links
de:Emtricitabin- Pages with script errors
- Pages with broken file links
- Infobox drug tracked parameters
- Articles without EBI source
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Gilead Sciences
- Nucleoside analog reverse transcriptase inhibitors
- World Health Organization essential medicines
- Pyrimidones
- Oxathiolanes
- Organofluorides
- 2Fix