ChemicalBook > CAS DataBase List > 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

Product Name
4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
CAS No.
500287-72-9
Chemical Name
4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
Synonyms
Rilpivirine;Rilpivirin;(E)-4-(4-(4-(2-cyanovinyl)-2,6-diMethylphenylaMino)pyriMidin-2-ylaMino)benzonitrile;TMC 278;DB08864;Pivelin;R 278474;pivirine;Rilpivirine(RPV);Rilpivirine, >=98%
CBNumber
CB81454833
Molecular Formula
C22H18N6
Formula Weight
366.42
MOL File
500287-72-9.mol
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4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile Property

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)
pka
4.56±0.10(Predicted)
form 
Solid
color 
Yellow
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Safety

Hazardous Substances Data
500287-72-9(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

H400Very toxic to aquatic life

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P330Rinse mouth.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
21559
Product name
Rilpivirine
Purity
≥98%
Packaging
1mg
Price
$29
Updated
2024/03/01
Cayman Chemical
Product number
21559
Product name
Rilpivirine
Purity
≥98%
Packaging
5mg
Price
$85
Updated
2024/03/01
Cayman Chemical
Product number
21559
Product name
Rilpivirine
Purity
≥98%
Packaging
10mg
Price
$156
Updated
2024/03/01
Cayman Chemical
Product number
21559
Product name
Rilpivirine
Purity
≥98%
Packaging
25mg
Price
$281
Updated
2024/03/01
TRC
Product number
R509800
Product name
Rilpivirine
Packaging
2.5mg
Price
$115
Updated
2021/12/16
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4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile Chemical Properties,Usage,Production

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. 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.

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.

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile Preparation Products And Raw materials

Raw materials

Preparation Products

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

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View Lastest Price from 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile manufacturers

Hebei Yanxi Chemical Co., Ltd.
Product
rilpivirine 500287-72-9
Price
US $0.00-0.00/KG
Min. Order
25KG
Purity
0.99
Supply Ability
5000kg/month
Release date
2024-04-26
Wuhan Senwayer Century Chemical Co.,Ltd
Product
Rilpivirine 500287-72-9
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 TONS
Release date
2022-11-08
Baoji Guokang Healthchem co.,ltd
Product
rilpivirine 500287-72-9
Price
US $1013.70/g
Min. Order
1g
Purity
98%
Supply Ability
100g
Release date
2021-06-04

500287-72-9, 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrileRelated Search:

LEE011 Zidovudine Ritonavir Efavirenz Tenofovir disoproxil Abacavir Icotinib Tenofovir Lapatinib Nevirapine GSK1349572 Raltegravir Etravirine Darunavir ethanolate SCH772984 Ripasudil hydrochloride dihydrate Riociguat DAPIVIRINE,4-[[4-(2,4,6-TRIMETHYLPHENYL)AMINO]PYRIMIDIN-2-YL]AMINO]BENZONITRILE

  • 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
  • (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-cyanoeth-1-en-1-yl]-2,6-diMethylphenyl}aMino)pyriMidin-2-yl]aMino}benzonitrile
  • Rilpivirine(R 278474
  • Rilpivirine (R 278474, TMC 278)
  • Rilpivirine
  • 4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile
  • R 278474
  • TMC 278
  • Benzonitrile,4-[[4-[[4-[(1E)-2-cyanoethenyl]-2,6-diMethylphenyl]aMino]-2-pyriMidinyl]aMino]-
  • Rilpivirin
  • 4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile Rilpivirine R 278474
  • R 278474; TMC 278; R-278474; R278474; TMC278; TMC-278
  • Rilpivirine, >=98%
  • DB08864
  • pivirine
  • BENZONITRILE。RILPIVIRINE
  • 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile USP/EP/BP
  • 4-[4-[4-[(E)-2-Cyanovinyl]-2,6-dimethylphenylamino]pyrimidin...
  • RilpivirineQ: What is Rilpivirine Q: What is the CAS Number of Rilpivirine Q: What is the storage condition of Rilpivirine Q: What are the applications of Rilpivirine
  • Pivelin
  • Rilpivirine/TMC-278
  • Rilpivirine(RPV)
  • Glycerol Impurity 39
  • 500287-72-9
  • C22H18N6
  • Aromatics
  • Heterocycles
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals