Emtricitabine

Structural formula
General
Non-proprietary name	Emtricitabine
other names	2 ', 3'-dideoxy-5-fluoro-3'-thiacytidine; FTC; (-) - 4-Amino-5-fluoro-1 - [(2 R , 5 S ) -2- (hydroxymethyl) -1,3-oxathiolan-5-yl] pyrimidin-2 (1 H ) -one;
Molecular formula	C 8 H 10 FN 3 O 3 S
External identifiers / databases
EC number	604-363-1
ECHA InfoCard	100.120.945
PubChem	60877
ChemSpider	54859
DrugBank	DB00879
Wikidata	Q422604
Drug information
ATC code	J05 AF09
Drug class	Antiviral
properties
Molar mass	247.27 g · mol -1
Physical state	firmly
Melting point	136-140 ° C
solubility	moderate in water (112 g l −1 )
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Emtricitabine , or FTC for short, is a chemical analogue of the nucleoside cytidine . It is a virostat from the group of nucleoside reverse transcriptase inhibitors ( NRTIs ) and is used as a medicinal substance for the treatment of HIV-1 and 2 infected patients as part of a combination antiretroviral therapy . In combination with tenofovir , it is also part of common drugs for HIV prophylaxis ( PrEP and PEP ); the combination preparation is approved under the trade name Truvada .

Emtricitabine is also effective against HBV .

structure

Emtricitabine differs structurally from the drug lamivudine only in the presence of a covalently bound fluorine atom at position 5 of the pyrimidine ring (see structural formula).

pharmacology

The nucleoside emtricitabine is phosphorylated to the nucleotide in the cell . Emtricitabine triphosphate is incorporated into the DNA in competition with the natural nucleotide deoxycytosine triphosphate (dCTP) . The incorporation of the dideoxynucleoside triphosphate leads to chain termination and inhibition of the viral reverse transcriptase .

Pharmacokinetics

Thanks to the long half-life (elimination half-life: 10 h, intracellular half-life of the triphosphate : 39 h), it can be used once a day.

literature

Analytics: Xenobiotica 96 26 (2), 189-199
Synthesis: Journal of Medical Chemistry 1993 36 (2), 181-195
Pharmacology: Biochem. Pharmacol. 1993, 45 (7), 1540-1543
Usage: The Journal of Infectious Diseases 2000 182 (2), 599-602
Journal of Antimicrobial Chemotherapy 2001 48 (4), 507-513

Trade names

Monopreparations

Emtriva [formerly Coviracil] (D, A, CH)

Combination preparations

Atripla (D, A, CH), Truvada (D, A, CH), Eviplera (D, A, CH), Stribild (D, A, CH), Genvoya, Odefsey, Symtuza

Web links

Public Assessment Report (EPAR) of the European Medicines Agency (EMA) for: Emtricitabine

Individual evidence

^ ^A ^b Entry on emtricitabine in the DrugBank of the University of Alberta .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) , Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10 -9 , p. 180.

[DrugBank-1] A ^b Entry on emtricitabine in the DrugBank of the University of Alberta .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Rote_Liste-3] Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) , Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10 -9 , p. 180.