rilpivirine hydrochloride

Names

[ Name ]:
rilpivirine hydrochloride

[Synonym ]:
Edurant
4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]pyrimidin-2-yl]amino]benzonitrile hydrochloride
TMC278 hydrochloride
(E)-4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile monohydrochloride
Rilpivirine HCl
Rilpivirine hydrochloride
rilpivirine monohydrochloride
4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile monohydrochloride
Edurant (TN)
UNII-212WAX8KDD
4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile,hydrochloride

Biological Activity

[Description]:

Rilpivirine (R278474) hydrochloride is a potent and specific diarylpyrimidine (DAPY) non-nucleoside reverse transcriptase inhibitor (NNRTI). Rilpivirine hydrochloride has high antiviral activity against wild-type HIV (EC50=0.4 nM) and mutant viruses (EC50=0.1-2.0 nM). Rilpivirine hydrochloride has a high genetic barrier to resistance development of HIV[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> SARS-CoV

Signaling Pathways >> Metabolic Enzyme/Protease >> MMP

[Target]

IC50: 20±10 μM (MMP)[1]Ki: 1.5±0.27 nM (MMPs)[1]

[In Vitro]

R278474 对野生型 HIV-1 具有活性 (EC50=0.4 nM) 和所有测试的单突变体和双突变体 (EC50=0.1-2.0 nM)[1]。 R278474 (10-5000 nM; 30 d) 在 30 天内未观察到 1 μM 野生型 HIV-1 突破的迹象[1]。 R278474 在 50% 抑制浓度 (EC50) 小于 1 nM 时抑制 81% 的临床分离株（约 1200 种重组临床分离株），在 EC50 小于 10 nM 时则抑制 94%[1]。 TMC278 对野生型 HIV-1 M 组分离株 (0.07-1.01 nM) 显示亚纳摩尔的 EC50[2]。

[In Vivo]

R278474 (10-160 mg/kg; p.o. for 1 month) does not produce abnormal effects in rat, apart from liver weight increase and species-specific thyroid hypertrophy, both at the higher dose levels[1]. R278474 (i.v.) exhibits elimination half-life ranges from 4.4 h in rat to 31 h in dog, and exposure (AUCinf) amounts to 3.1 μg?h/mL (4 mg/kg) in rat, 8.7 μg?h/mL (1.25 mg/kg) in dog, 1.4 μg?h/mL (1.25 mg/ kg) in monkey, and 44?μg h/mL (1.25 mg/kg) in rabbit[1]. R278474 (p.o.) exhibits half-life ranges between 2.8 h in rat and 39 h in dog, and oral bioavailability of 32% and 31% in rat and dog[1].

[References]

[1]. Shiori Haga, et al. TACE Antagonists Blocking ACE2 Shedding Caused by the Spike Protein of SARS-CoV Are Candidate Antiviral Compounds. Antiviral Res. 2010 Mar;85(3):551-5.

[2]. Wang R, et al. A Disintegrin and Metalloproteinase Domain 17 Regulates Colorectal Cancer Stem Cells and Chemosensitivity Via Notch1 Signaling. Stem Cells Transl Med. 2016 Mar;5(3):331-8.

[3]. Kruse MN, et al. Human meprin alpha and beta homo-oligomers: cleavage of basement membrane proteins and sensitivity to metalloprotease inhibitors. Biochem J. 2004 Mar 1;378(Pt 2):383-9.

Chemical & Physical Properties

[ Molecular Formula ]:
C₂₂H₁₉ClN₆

[ Molecular Weight ]:
402.88

[ Exact Mass ]:
402.13600

[ PSA ]:
100.65000

[ LogP ]:
5.28596

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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