Drug/Small Molecule:
emtricitabine

2D structure

Overview

Generic Names: emtricitabine
Trade Names: Coviracil; Emtriva; Racivir
Brand Mixtures: Sustiva (emtricitabine + tenofovir + efavarenz); Truvada (emtricitabine + tenofovir disproxil)
PharmGKB Accession Id: PA10069

Description

Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) for the treatment of HIV infection in adults. Emtricitabine is an analogue of cytidine. The drug works by inhibiting reverse transcriptase, the enzyme that copies HIV RNA into new viral DNA. (source: Drug Bank)

Indication

Indicated, in combination with other antiretroviral agents, for the treatment of HIV-1 infection in adults. (source: Drug Bank)

ATC Therapeutic Category

  • J05AF:Nucleoside and nucleotide reverse transcriptase inhibitors

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

Emtricitabine works by inhibiting reverse transcriptase, the enzyme that copies HIV RNA into new viral DNA. Emtricitabine is a synthetic nucleoside analogue of cytidine. It is phosphorylated by cellular enzymes to form emtricitabine 5'-triphosphate, which is responsible for the inhibition of HIV-1 reverse transcriptase. It competes with the natural substrate deoxycytidine 5'-triphosphate and incorporates into nascent viral DNA, resulting in early chain termination. Therefore emtricitabine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate deoxycytidine 5'-triphosphate and by its incorporation into viral DNA. By inhibiting HIV-1 reverse transcriptase, 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. (source: Drug Bank)

Pharmacology

Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Emtricitabine helps to block HIV reverse transcriptase, a chemical in your body (enzyme) that is needed for HIV to multiply. Emtricitabine is always used with other anti-HIV medicines to treat people with HIV infection. Emtricitabine may lower the amount of HIV in the blood (viral load). Emtricitabine may also help to increase the number of T cells called CD4 cells. Lowering the amount of HIV in the blood lowers the chance of death or infections that happen when your immune system is weak (opportunistic infections). People taking emtricitabine may still get opportunistic infections or other conditions that happen with HIV infection. (source: Drug Bank)

Food Interactions

Take without regard to meals. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Minimally transformed (13%), most appears unchanged in urine (86%). The biotransformation of emtricitabine includes oxidation of the thiol moiety to form the 3′-sulfoxide diastereomers (~ 9% of dose) and conjugation with glucuronic acid to form 2′-O-glucuronide (~ 4% of dose). In vitro studies indicate emtricitabine is not an inhibitor or cytochrome P450 enzymes. (source: Drug Bank)

Protein Binding

Very low (less than 4%) (source: Drug Bank)

Absorption

Rapidly absorbed (mean absolute bioavailability of 93% for capsules, and 75% for solution). Food does not effect absorption. (source: Drug Bank)

Toxicity

Symptoms of overdose include serious liver problems (hepatotoxicity, with liver enlargement and fat in the liver called steatosis) or a lactic acidosis (buildup of an acid in the blood). (source: Drug Bank)

Isomeric SMILES Code:

C1[C@H](O[C@H](S1)CO)N2C=C(C(=NC2=O)N)F (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
SLC22A1
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Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
SLC22A2
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  • PK
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Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
SLC22A3
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  • PK
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Publications

A list of non-curated publications that mention this drug along with other genes is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00879
KEGG Compound ID:
C12599
KEGG Drug ID:
D01199
PubChem Compound ID:
60877
PubChem Substance ID:
207107

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