3DChem.com - Chemistry, Structures & 3D Molecules a visual and interactive website showcasing the beautiful world of chemistry

Efavirenz (Molecule of the Month for April 2007)

Sustiva, Stocrin, HIV, AIDS



Efavirenz is a non-nucleoside reverse transcriptase inhibitor (NNRTI) and is used as part of highly active antiretroviral therapy (HAART) for the treatment of a human immunodeficiency virus (HIV) type 1. For HIV infection that has not previously been treated, efavirenz and lamivudine in combination with zidovudine or tenofovir is the preferred NNRTI-based regimen. It is never used alone and is always given in combination with other drugs.

Efavirenz falls in the non-nucleoside reverse transcriptase inhibitor (NNRTI) class of antiretrovirals. Both nucleoside and non-nucleoside RTIs inhibit the same target, the reverse transcriptase enzyme, an essential viral enzyme which transcribes viral RNA into DNA. Unlike nucleoside RTIs, which bind at the enzyme's active site, NNRTIs bind within a pocket termed the NNRTI pocket. Efavirenz is not effective against HIV-2, as the pocket of the HIV-2 reverse transcriptase has a different structure, which confers intrinsic resistance to the NNRTI class

Formal Chemical Name (IUPAC)
(S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1H-benzo[d][1,3]oxazin-2(4H)-one

References

http://en.wikipedia.org/wiki/Efavirenz

http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a699004.html

Picture of Efavirenz

click on the picture above to interact
with the 3D model of the
Efavirenz structure
(this will open a new browser window)

Picture of Efavirenz

C14 H9 Cl F3 N O2



Update by Karl Harrison
(Molecule of the Month for April 2007 )