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
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
- InChI
- InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+
- InChIKey
- YIBOMRUWOWDFLG-ONEGZZNKSA-N
- SMILES
- C(#N)C1=CC=C(NC2=NC=CC(NC3=C(C)C=C(/C=C/C#N)C=C3C)=N2)C=C1
Safety
- Hazardous Substances Data
- 500287-72-9(Hazardous Substances Data)
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..…
N-Bromosuccinimide Price
- Product number
- 21559
- Product name
- Rilpivirine
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $29
- Updated
- 2024/03/01
- Product number
- 21559
- Product name
- Rilpivirine
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $85
- Updated
- 2024/03/01
- Product number
- 21559
- Product name
- Rilpivirine
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $156
- Updated
- 2024/03/01
- Product number
- 21559
- Product name
- Rilpivirine
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $281
- Updated
- 2024/03/01
- Product number
- R509800
- Product name
- Rilpivirine
- Packaging
- 2.5mg
- Price
- $115
- Updated
- 2021/12/16
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
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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
- Product
- (E)-4-((4-((4-(2-Cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile 500287-72-9
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- Customise
- Release date
- 2025-11-25
- 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
- Product
- Rilpivirine 500287-72-9
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20 TONS
- Release date
- 2022-11-08