Nevirapine

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Structural formula
Structural formula of nevirapine
General
Non-proprietary name Nevirapine
other names

11-Cyclopropyl-4-methyl-5,11-dihydro-6 H -dipyrido [3,2- b : 2,3- e ] - [1,4] diazepin-6-one

Molecular formula C 15 H 14 N 4 O
Brief description

white to almost white powder

External identifiers / databases
CAS number
PubChem 4463
DrugBank DB00238
Wikidata Q263713
Drug information
ATC code

J05 AG01

Drug class

Antivirals , non-nucleoside reverse transcriptase inhibitors

Mechanism of action

non-competitive inhibition of reverse transcriptase

properties
Molar mass 266.30 g · mol -1
Physical state

firmly

Melting point

247-249 ° C

pK s value

2.8

solubility

practically insoluble in water, sparingly soluble to sparingly soluble in dichloromethane , sparingly soluble in methanol

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

400 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nevirapine (NVP, trade name Viramune ® ; manufacturer Boehringer Ingelheim ) is a drug for the treatment of HIV-1 infected patients as part of a combination antiretroviral therapy .

history

Nevirapine was the first approved member of the class of non-nucleoside reverse transcriptase inhibitors (NNRTIs). It was approved in the USA in 1996 and in Europe in 1997.

pharmacology

Nevirapine binds non-competitively to the reverse transcriptase of HIV-I , near the substrate binding site for nucleosides . This blocks the catalytically active binding site. Fewer nucleosides can now bind and the polymerization is significantly slowed down. Due to the mechanism of action, a simple mutation of the binding site makes it possible for the HIV virus to develop resistance. This also results in resistance to other non-nucleosidic RT inhibitors, since these have a common binding site. It is therefore only recommended to use it in combination therapy.

There is no effect on HIV-II because it has a different binding site.

Individual evidence

  1. ↑ a b c data sheet ANHYDROUS NEVIRAPINE CRS (PDF) at EDQM , accessed on February 26, 2009.
  2. ↑ a b entry on nevirapine. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.
  3. ↑ a b Nevirapine data sheet from Sigma-Aldrich , accessed on October 31, 2016 ( PDF ).
  4. ↑ Grant D. Schauer, Kelly D. Huber, Sanford H. Leuba, Nicolas Sluis-Cremer: Mechanism of allosteric inhibition of HIV-1 reverse transcriptase revealed by single-molecule and ensemble fluorescence . In: Nucleic Acids Research . tape 42 , no. 18 , October 13, 2014, p. 11687–11696 , doi : 10.1093 / nar / gku819 , PMC 4191400 (free full text).