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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

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
Molecular Weight:
366.42
MDL Number:
MFCD11046372
MOL File:
500287-72-9.mol
MSDS File:
SDS
Last updated:2025-01-27 09:38:02

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

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
FDA UNII FI96A8X663
ATC code J05AG05
UNSPSC Code 51111800
NACRES NA.77

Pharmacokinetic data

Protein binding 99.7%
Excreted unchanged in urine <1%
Biological half-life 45

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS09
Signal word  Warning
Hazard statements  H319-H400-H302-H410
Precautionary statements  P273-P391-P501-P264-P270-P301+P312-P330-P501-P273-P391-P501-P264-P280-P305+P351+P338-P337+P313P
Hazardous Substances Data 500287-72-9(Hazardous Substances Data)
NFPA 704
0
2 0

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile price More Price(31)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 21559 Rilpivirine ≥98% 500287-72-9 1mg $29 2024-03-01 Buy
Cayman Chemical 21559 Rilpivirine ≥98% 500287-72-9 5mg $85 2024-03-01 Buy
Cayman Chemical 21559 Rilpivirine ≥98% 500287-72-9 10mg $156 2024-03-01 Buy
Cayman Chemical 21559 Rilpivirine ≥98% 500287-72-9 25mg $281 2024-03-01 Buy
TRC R509800 Rilpivirine 500287-72-9 2.5mg $115 2021-12-16 Buy
Product number Packaging Price Buy
21559 1mg $29 Buy
21559 5mg $85 Buy
21559 10mg $156 Buy
21559 25mg $281 Buy
R509800 2.5mg $115 Buy

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

500288-66-4
500287-72-9
Synthesis of 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile from 3-{4-[2-(4-Cyano-phenylamino)-1-oxy-pyrimidin-4-ylamino]-3,5-dimethyl-phenyl}-acrylamide

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

Global( 259)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Yanxi Chemical Co., Ltd. 		+8617531153977 allison@yan-xi.com China 5855 58
Capot Chemical Co.,Ltd. 		+86-（0）57185586718 +86-13336195806 sales@capot.com China 29730 60
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21631 55
Nanjing ChemLin Chemical Industry Co., Ltd. 		025-83697070 product@chemlin.com.cn CHINA 3009 60
ATK CHEMICAL COMPANY LIMITED 		+undefined-21-51877795 ivan@atkchemical.com China 33025 60
career henan chemical co 		+86-0371-86658258 +8613203830695 sales@coreychem.com China 29865 58
Shaanxi Yikanglong Biotechnology Co., Ltd. 		17791478691 yklbiotech@163.com CHINA 296 58
Biochempartner 		0086-13720134139 candy@biochempartner.com CHINA 965 58
Hubei xin bonus chemical co. LTD 		86-13657291602 linda@hubeijusheng.com CHINA 22963 58
BOC Sciences 		+1-631-485-4226 inquiry@bocsci.com United States 19552 58

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

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
rilpivirine pictures 2025-03-07 rilpivirine
500287-72-9
 US $0.00-0.00 / KG 25KG 0.99 5000kg/month Hebei Yanxi Chemical Co., Ltd.
Rilpivirine pictures 2024-11-19 Rilpivirine
500287-72-9
 US $32.00-80.00 / mg 98.83% 10g TargetMol Chemicals Inc.
Rilpivirine pictures 2024-09-25 Rilpivirine
500287-72-9
 US $0.00 / KG 1KG 99% 20 TONS Wuhan Senwayer Century Chemical Co.,Ltd
  • rilpivirine pictures
  • rilpivirine
    500287-72-9
  • US $0.00-0.00 / KG
  • 0.99
  • Hebei Yanxi Chemical Co., Ltd.
  • Rilpivirine pictures
  • Rilpivirine
    500287-72-9
  • US $32.00-80.00 / mg
  • 98.83%
  • TargetMol Chemicals Inc.
  • Rilpivirine pictures
  • Rilpivirine
    500287-72-9
  • US $0.00 / KG
  • 99%
  • Wuhan Senwayer Century Chemical Co.,Ltd

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

4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]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) 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]- 4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile Rilpivirine R 278474 Rilpivirine, >=98% R 278474; TMC 278; R-278474; R278474; TMC278; TMC-278 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 (E)-4-(4-(4-(2-cyanovinyl)-2,6-diMethylphenylaMino)pyriMidin-2-ylaMino)benzonitrile Rilpivirine Rilpivirin Pivelin Rilpivirine/TMC-278 Rilpivirine(RPV) Glycerol Impurity 39 Rilpivirine, 10 mM in DMSO 500287-72-9 C22H18N6 Aromatics Heterocycles Inhibitors Intermediates & Fine Chemicals Pharmaceuticals