ChemicalBook Produktkatalog Bio- und Chemieingenieurwesen Inhibitoren Mikrobiologie Reverse Transkriptase-Inhibitoren 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile Struktur

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile

Bezeichnung:4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile

CAS-Nr500287-72-9

Englisch Name:4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile

CBNumberCB81454833

SummenformelC22H18N6

Molgewicht366.42

MOL-Datei500287-72-9.mol

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile physikalisch-chemischer Eigenschaften

Schmelzpunkt	245℃
Siedepunkt	634.1±65.0 °C(Predicted)
Dichte	1.27
storage temp.	Refrigerator
Löslichkeit	Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Water (Very Slightly)
pka	4.56±0.10(Predicted)
Aggregatzustand	Solid
Farbe	Yellow

Sicherheit

Giftige Stoffe Daten

500287-72-9(Hazardous Substances Data)

Gefahreninformationscode (GHS)

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Chemische Eigenschaften
N/ABright Yellow Solid
Originator
Janssen (Belgium)
Verwenden
A novel non-nucleoside reverse transcriptase inhibitor. Rilpivirine seems to be well tolerated with less CNS disturbance than Efavirenz, and has non-teratogenic potential. An anti-HIV agent.
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.
Trademarks
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
Arzneimittelwechselwirkung
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.
Stoffwechsel
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.
Lager
Store at -20°C
Einzelnachweise
[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.

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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