Rilpivirine

Names

[ Name ]:
Rilpivirine

[Synonym ]:
[3H]-Rilpivirine
Edurant
Rilpivirine
TMC-278
4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile
4-{[4-({4-[(E)-2-Cyanovinyl]-2,6-dimethylphenyl}amino)-2-pyrimidinyl]amino}benzonitrile
Benzonitrile, 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]-
UNII-FI96A8X663
R 278474
BENZONITRILE,4-((4-((4-((1E)-2-CYANOETHEN YL)-2,6-DIMETHYLPHENYL)AMINO)-2-PYRIMIDINYL)AMINO)-)

Biological Activity

[Description]:

Rilpivirine (R278474; TMC278) is a type of anti-HIV medicine called a non-nucleoside reverse transcriptase inhibitor (NNRTI).

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV

Signaling Pathways >> Anti-infection >> Reverse Transcriptase

Research Areas >> Infection

[Target]

NNRTIs

[In Vitro]

Rilpivirine(TMC278) is a next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI), active against wild-type and NNRTI-resistant HIV-1. NNRTIs work by binding to and blocking HIV reverse transcriptase, an HIV enzyme. This prevents HIV from replicating and lowers the amount of HIV in the blood.

[References]

[1]. Singh K, Marchand B, Rai DK, Sharma B, Michailidis E, Ryan EM, Matzek KB, Leslie MD, Hagedorn AN, Li Z, Norden PR, Hachiya A, Parniak MA, Xu HT, Wainberg MA, Sarafianos SG.Biochemical Mechanism of HIV-1 Resistance to Rilpivirine.J Biol Chem. 2012 Sep 6.

[2]. Schafer JJ, Short WR.Rilpivirine, a novel non-nucleoside reverse transcriptase inhibitor for the management of HIV-1 infection: a systematic review.Antivir Ther. 2012 Jul 25.

[3]. Vingerhoets J, Rimsky L, Van Eygen V, Nijs S, Vanveggel S, Boven K, Picchio G.Preexisting mutations in the rilpivirine Phase III trials ECHO and THRIVE: prevalence and impact on virologic response.Antivir Ther. 2012 Sep 6.

[4]. Gomes T, Juurlink DN, Mamdani MM.Comparative adherence to oxybutynin or tolterodine among older patients.Eur J Clin Pharmacol. 2012 Jan;68(1):97-9. Epub 2011 Jun 28.

[5]. Azijn, Hilde et al. TMC278, a next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI), active against wild-type and NNRTI-resistant HIV-1.Antimicrobial Agents and Chemotherapy (2010), 54(2), 718-727.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
634.1±65.0 °C at 760 mmHg

[ Melting Point ]:
245ºC

[ Molecular Formula ]:
C₂₂H₁₈N₆

[ Molecular Weight ]:
366.418

[ Flash Point ]:
337.3±34.3 °C

[ Exact Mass ]:
366.159302

[ PSA ]:
97.42000

[ LogP ]:
3.63

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.665

[ Storage condition ]:
Refrigerator

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2933599090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%