Etravirine (TMC125) , ≥95% , 269055-15-4

CAS NO.：269055-15-4

Empirical Formula: C20H15BrN6O

Molecular Weight: 435.28

MDL number: MFCD09837879

EINECS: 682-331-6

PRODUCT Properties

• Melting point: .265°C (dec.)
• Boiling point: 637.4±65.0 °C(Predicted)
• Density: 1.439 g/cm3
• storage temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• form: Solid
• pka: 1.23±0.10(Predicted)
• color: White to Off-White

Description and Uses

Etravirine is a second-generation NNRTI. It is indicated for use in combination with other antiretroviral agents for treating HIV-1 infection in treatment-experienced adult patients who have evidence of viral replication and HIV-1 strains resistant to the currently available NNRTIs and other antiretroviral agents. The NNRTIs, along with nucleoside/nucleotide reverse transcriptase inhibitors (NRTIs/NtRTIs), are important components of the combination regimens currently used to treat HIV-1 infection. The NRTIs/NtRTIs act by competing with the natural nucleotide substrates of reverse transcriptase for incorporation into viral DNA and subsequent chain termination. By contrast, the NNRTIs bind to an allosteric site of the enzyme and disrupt the DNA polymerase function by inducing conformational changes to the catalytic site. The allosteric binding nature of NNRTIs generally results in improved safety profile since there is no known human homolog for the drug-binding site of the enzyme.
As with other NNRTIs, etravirine has many drug–drug interactions. It is a substrate of CYP3A4, CYP2C9, and CYP2C19, an inducer of 3A4, and an inhibitor of 2C9 and 2C19. Caution should be used with co-administration of inducers, inhibitors, or substrates of these enzymes. Etravirine can be synthesized starting from 5-bromo-2,4,6-trichloropyrimidine through three successive nucleophilic substitution reactions. Initial displacement with 4-aminobenzonitrile using Hu¨nig’s base, followed by reaction with sodium salt of 4-hydroxy-3,5- dimethylbenzonitrile, and subsequent ammonolysis reaction with ammonia in dioxane under pressure affords etravirine. .

Etravirine is a novel HIV reverse transcriptase inhibitor useful in treatment of HIV infection.

Safety

• Symbol(GHS): GHS09
• Signal word: Warning
• Hazard statements: H410
• Precautionary statements: P273-P391-P501