Nevirapine
Structural formula | |||||||||||||
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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 |
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Molecular formula | C 15 H 14 N 4 O | ||||||||||||
Brief description |
white to almost white powder |
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External identifiers / databases | |||||||||||||
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Drug information | |||||||||||||
ATC code | |||||||||||||
Drug class |
Antivirals , non-nucleoside reverse transcriptase inhibitors |
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Mechanism of action |
non-competitive inhibition of reverse transcriptase |
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properties | |||||||||||||
Molar mass | 266.30 g · mol -1 | ||||||||||||
Physical state |
firmly |
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Melting point |
247-249 ° C |
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pK s value |
2.8 |
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solubility |
practically insoluble in water, sparingly soluble to sparingly soluble in dichloromethane , sparingly soluble in methanol |
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safety instructions | |||||||||||||
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Toxicological data | |||||||||||||
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
- ↑ a b c data sheet ANHYDROUS NEVIRAPINE CRS (PDF) at EDQM , accessed on February 26, 2009.
- ↑ a b entry on nevirapine. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.
- ↑ a b Nevirapine data sheet from Sigma-Aldrich , accessed on October 31, 2016 ( PDF ).
- ↑ 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).