emtricitabine   Click here for help

GtoPdb Ligand ID: 11244

Abbreviated name: FTC
Synonyms: 524W91 | BW-524W91 | Coviracil® | Emtriva®
Approved drug PDB Ligand
emtricitabine is an approved drug (EMA & FDA (2003))
Compound class: Synthetic organic
Comment: Emtricitabine is a nucleoside reverse transcriptase inhibitor (NRTI) antiretroviral compound.
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View more information in the IUPHAR Pharmacology Education Project: emtricitabine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 115.67
Molecular weight 247.04
XLogP 0.28
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES Nc1nc(=O)n(cc1F)[C@@H]1CS[C@@H](O1)CO
Isomeric SMILES Nc1nc(=O)n(cc1F)[C@@H]1CS[C@@H](O1)CO
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
InChI Key XQSPYNMVSIKCOC-NTSWFWBYSA-N
No information available.
Summary of Clinical Use Click here for help
Emtricitabine is used in the treatment of HIV-1 infection in combination with other antiretroviral agents.

SARS-CoV-2 and COVID-19: A number of Phase 2/3 clinical trials are planned to evaluate the use of emtricitabine/tenofovir to prevent SARS-COV-2 transmission to healthcare professionals.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Emtricitabine is an analogue of cytidine and is a reverse transciptase inhibitor, preventing viral replication.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04334928 Randomized Clinical Trial for the Prevention of SARS-CoV-2 Infection (COVID-19) in Healthcare Personnel Phase 3 Interventional Plan Nacional sobre el Sida (PNS)
NCT04519125 Daily Regimen of Tenofovir/Emtricitabine as Prevention for COVID-19 in Health Care Personnel in Colombia Phase 2/Phase 3 Interventional Hospital Universitario San Ignacio
NCT04405271 TAF/FTC for Pre-exposure Prophylaxis of COVID-19 in Healthcare Workers (CoviPrep Study) Phase 3 Interventional Hospital Italiano de Buenos Aires
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)