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ChemicalBook--->CAS DataBase List--->500287-72-9

500287-72-9

500287-72-9 Structure

500287-72-9 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Hazardous Substances Data]

500287-72-9(Hazardous Substances Data)
Hazard InformationBack 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.
Spectrum DetailBack Directory
[Spectrum Detail]

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile(500287-72-9)1HNMR
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