Etravirine

Structural formula
General
Non-proprietary name	Etravirine
other names	4- [6-Amino-5-bromo-2- (4-cyanophenylamino) pyrimidin-4-yloxy] -3,5-dimethylbenzonitrile ( IUPAC ); TMC-125;
Molecular formula	C 20 H 15 BrN 6 O
External identifiers / databases
EC number	682-331-6
ECHA InfoCard	100.207.546
PubChem	193962
ChemSpider	168313
DrugBank	DB06414
Wikidata	Q414762
Drug information
ATC code	J05 AG04
Drug class	Antivirals , non-nucleoside reverse transcriptase inhibitors
Mechanism of action	non-competitive inhibition of reverse transcriptase
properties
Molar mass	435.28 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-413
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Etravirine (ETV, trade name: Intelence ^® ; manufacturer: Tibotec ) is a drug used to treat HIV- infected patients as part of an HIV combination therapy .

Etravirine belongs to the class of non-nucleoside reverse transcriptase inhibitors (NNRTIs).

history

Intelence, in combination with other anti retroviral drugs, was approved for the treatment of HIV-1 infections in unsuccessful patients in the United States in January 2008 and in the European Union in August 2008.

pharmacology

Etravirine belongs to the class of non-nucleoside reverse transcriptase inhibitors (NNRTIs). The active ingredient binds non-competitively to the reverse transcriptase of HIV-I , near the substrate binding site for nucleosides . This blocks the catalytically active binding site. Only a few nucleosides can bind and the polymerization is slowed down significantly.

Side effects

In general, etravirine is well tolerated, although some studies reported the side effects typical of NNRTIs, dizziness and rash. However, the side effects rarely led to therapy discontinuation.

In mid-2009, the manufacturer announced that there had been a death from Lyell's syndrome and hypersensitivity reactions combined with liver failure .

Resistances

Compared to other NNRTIs, etravirine has the advantage that, in addition to being very effective against the wild type, it is also very effective against most NNRTI-resistant strains. In phase I / II studies, etravirine showed its high potency in lowering viral loads.

Web links

AIDSMeds.com
New in the EAP: NNRTI etravirine (PDF file; 290 kB)
European Public Assessment Report (EPAR) and product information for Intelence on the European Medicines Agency website

Individual evidence

↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 4- (6-Amino-5-bromo-2- (4-cyanoanilino) pyrimidin-4-yloxy) -3,5-dimethylbenzonitrile in the Classification and Labeling Inventory of the European Chemicals Agency ( ECHA), accessed on February 10, 2020.
↑ Kakuda 2006.
↑ Tibotec Therapeutics: Intelence: Important Drug Warning , August 2009 (PDF; 74 kB). Retrieved August 27, 2009.
↑ B. Gruzdev, A. Rakhmanova, E. Doubovskaya et al .: A randomized, double-blind, placebo-controlled trial of TMC125 as 7-day monotherapy in antiretroviral naive, HIV-1 infected subjects. In: AIDS . 17, 2003, pp. 2487-2494. PMID 14600520 .

[1] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 4- (6-Amino-5-bromo-2- (4-cyanoanilino) pyrimidin-4-yloxy) -3,5-dimethylbenzonitrile in the Classification and Labeling Inventory of the European Chemicals Agency ( ECHA), accessed on February 10, 2020.

[2] Kakuda 2006.

[3] Tibotec Therapeutics: Intelence: Important Drug Warning , August 2009 (PDF; 74 kB). Retrieved August 27, 2009.

[4] B. Gruzdev, A. Rakhmanova, E. Doubovskaya et al .: A randomized, double-blind, placebo-controlled trial of TMC125 as 7-day monotherapy in antiretroviral naive, HIV-1 infected subjects. In: AIDS . 17, 2003, pp. 2487-2494. PMID 14600520 .