| Identification | Back Directory | [Name]
4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile | [CAS]
500287-72-9 | [Synonyms]
TMC 278
DB08864
pivirine
R 278474
Rilpivirin
Rilpivirine
Rilpivirine, >=98%
Rilpivirine(R 278474
BENZONITRILE。RILPIVIRINE
Rilpivirine (R 278474, TMC 278)
R 278474; TMC 278; R-278474; R278474; TMC278; TMC-278
(E)-4-(4-(4-(2-cyanovinyl)-2,6-diMethylphenylaMino)pyriMidin-2-ylaMino)benzonitrile
4-[[4-[[4-[(E)-2-Cyanovinyl]-2,6-diMethylphenyl]aMino]pyriMidin-2-yl]aMino]benzonitrile
4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile
4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
Benzonitrile,4-[[4-[[4-[(1E)-2-cyanoethenyl]-2,6-diMethylphenyl]aMino]-2-pyriMidinyl]aMino]-
4-{[4-({4-[(1E)-2-cyanoeth-1-en-1-yl]-2,6-diMethylphenyl}aMino)pyriMidin-2-yl]aMino}benzonitrile
4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile USP/EP/BP
4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile Rilpivirine R 278474 | [Molecular Formula]
C22H18N6 | [MDL Number]
MFCD11046372 | [MOL File]
500287-72-9.mol | [Molecular Weight]
366.42 |
| Chemical Properties | Back Directory | [Melting point ]
245℃ | [Boiling point ]
634.1±65.0 °C(Predicted) | [density ]
1.27 | [storage temp. ]
Refrigerator | [solubility ]
Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Water (Very Slightly) | [form ]
Solid | [pka]
4.56±0.10(Predicted) | [color ]
Yellow |
| Hazard Information | Back Directory | [Description]
In May 2011, the U.S. FDA approved rilpivirine in combination with other
antiretroviral agents for the treatment of human immunodeficiency virus
(HIV) 1 infection in treatment-naive adult patients.
Rilpivirine is a member of the nonnucleoside reverse transcriptase inhibitor (NNRTI) class of anti-HIV
agents. It is highly potent against a range of wild-type HIV strains
(EC50=0.07–1.0 nM),～10–20 timesmore potent than the NNRTI efavirenz
(Sustiva), and active against HIV strains resistant to other NNRTIs. The
discovery of rilpivirine was guided by molecular modeling and X-ray
crystallography of HIV-1 RT complexed with inhibitors. The synthesis
of rilpivirine is accomplished by an efficient 6-step route in which the key
step is coupling of 4-((4-chloropyrimidin-2-yl)amino)benzonitrile with (E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile. | [Chemical Properties]
N/ABright Yellow Solid | [Originator]
Janssen (Belgium) | [Uses]
A novel non-nucleoside reverse transcriptase inhibitor. Rilpivirine seems to be well tolerated with less CNS disturbance than Efavirenz, and has non-teratogenic potential. | [Definition]
ChEBI: An aminopyrimidine that is pyrimidine-2,4-diamine in which the amino groups at positions 2 and 4 are substituted by 4-cyanophenyl and 4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl groups respectively. Used for treatment of HIV. | [Brand name]
Edurant | [Clinical Use]
Non-nucleoside reverse transcriptase inhibitor:
Treatment of progressive or advanced HIV infection
in combination with at least two other antivirals | [target]
reverse transcriptase | [Drug interactions]
Potentially hazardous interactions with other drugs
Antibacterials: avoid with clarithromycin and
erythromycin - concentration possibly increased;
concentration decreased by rifampicin and rifabutin
- avoid with rifampicin, increase dose of rilpivirine
to 50 mg daily.
Antidepressants: concentration possibly reduced by
St John’s wort - avoid.
Antiepileptics: concentration possibly reduced
by carbamazepine, fosphenytoin, oxcarbazepine,
phenobarbital, primidone and phenytoin - avoid.
Corticosteroids: avoid with dexamethasone (except
as a single dose).
Orlistat: absorption possibly reduced by orlistat.
Ulcer-healing drugs: concentration possibly reduced
by esomeprazole, lansoprazole, omeprazole,
pantoprazole and rabeprazole - avoid; avoid
histamine H2
-antagonists for 12 hours before and 4
hours after rilpiverine. | [Metabolism]
Primarily undergoes oxidative metabolism mediated by
the cytochrome P450 (CYP) 3A system.
85% excreted via the faeces (25% as unchanged drug) and
6% via the urine. | [storage]
Store at -20°C | [References]
[1] moss d m, liptrott n j, curley p, et al. rilpivirine inhibits drug transporters abcb1, slc22a1, and slc22a2 in vitro. antimicrobial agents and chemotherapy, 2013, 57(11): 5612-5618.
[2] garvey l, winston a. rilpivirine: a novel non-nucleoside reverse transcriptase inhibitor. 2009.
[3] weiss j, haefeli w e. potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. international journal of antimicrobial agents, 2013, 41(5): 484-487.
[4] baert l, van’t klooster g, dries w, et al. development of a long-acting injectable formulation with nanoparticles of rilpivirine (tmc278) for hiv treatment. european journal of pharmaceutics and biopharmaceutics, 2009, 72(3): 502-508. |
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