10243. Etravirine

Nomenclature

CAS number: 269055-15-4
4-[[6-Amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethylbenzonitrile; 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile; R-165335; TMC-125; Intelence (Tibotec).
C20H15BrN6O; mol wt 435.28.
C 55.19%, H 3.47%, Br 18.36%, N 19.31%, O 3.68%.

Description and references

Diarylpyrimidine, nonnucleoside reverse transcriptase inhibitor (NNRTI). Prepn: B. De Corte et al., WO 0027825; eidem, US 7037917 (2000, 2006, both to Janssen); and anti-HIV activity: D. W. Ludovici et al., Bioorg. Med. Chem. Lett. 11, 2235 (2001) DOI PubMed. Crystal structure of complex with HIV reverse transcriptase: K. Das et al., J. Med. Chem. 47, 2550 (2004) DOI PubMed. Antiretroviral spectrum and resistance potential: J. Vingerhoets et al., J. Virol. 79, 12773 (2005) DOI PubMed. Clinical pharmacokinetics and antiretroviral activity in drug-resistant patients: M. Boffito et al., AIDS 21, 1449 (2007) DOI PubMed. Clinical trials in treatment experienced patients: J. V. Madruga et al., Lancet 370, 29 (2007) DOI PubMed; A. Lazzarin et al., ibid. 39 DOI PubMed.

Chemical structure

Properties

Crystals from acetonitrile, mp 255°.

Therapeutic Category

Antiretroviral.

Keywords

Reverse Transcriptase Inhibitor; Antiretroviral; Reverse Transcriptase Inhibitors; Nonnucleosides