Cas no 500287-72-9 (Rilpivirine)

Rilpivirine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used in the treatment of HIV-1 infection. It exhibits high potency against wild-type HIV-1 strains, with a favorable resistance profile compared to earlier NNRTIs. The compound demonstrates strong binding affinity to reverse transcriptase, effectively inhibiting viral replication. Its low daily dosage (25 mg) and compatibility with once-daily oral administration enhance patient adherence. Rilpivirine is often formulated in combination therapies, such as with tenofovir and emtricitabine, to improve efficacy. It has a reduced risk of neuropsychiatric side effects compared to other NNRTIs, making it a suitable option for long-term treatment regimens. Its stability and bioavailability are optimized in tablet formulations.
Rilpivirine structure
Rilpivirine structure
Product Name:Rilpivirine
CAS No:500287-72-9
MF:C22H18N6
MW:366.418523311615
MDL:MFCD11046372
CID:374628
PubChem ID:6451164
Update Time:2025-05-23

Rilpivirine Chemical and Physical Properties

Names and Identifiers

    • Benzonitrile,4-[[4-[[4-[(1E)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]-
    • Rilpivirine
    • (E)-4-(4-(4-(2-Cyanovinyl)-2,6-dimethylphenylamino)pyrimidin-2-ylamino)benzonitrile
    • 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
    • 4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile
    • Ripivirine
    • [3H]-Rilpivirine
    • Edurant
    • R 278474
    • R-278474
    • TMC 278
    • TMC-278
    • UNII-FI96A8X663
    • 4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile
    • TMC278
    • R278474
    • 4-{[4-({4-[(E)-2-Cyanoethenyl]-2,6-Dimethylphenyl}amino)pyrimidin-2-Yl]amino}benzonitrile
    • FI96A8X663
    • 4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
    • (E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile
    • (E)-4-(4-(4-(2-cyanovinyl)-2,6-d
    • MFCD11046372
    • HY-10574
    • 500287-72-9 (free base)
    • BCP9000016
    • YIBOMRUWOWDFLG-ONEGZZNKSA-N
    • BCP03563
    • T27
    • DB08864
    • 4-((4-((4-((E)-2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile
    • CHEMBL175691
    • 500287-72-9
    • RILPIVIRINE [ORANGE BOOK]
    • A827939
    • Edurant(TM)
    • CS-0440
    • EN300-21682062
    • R278474;TMC278
    • 4-{[4-({4-[(1E)-2-cyanoeth-1-en-1-yl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
    • D09720
    • RILPIVIRINE [JAN]
    • 4-{4-[4-((E)-2-Cyano-vinyl)-2,6-dimethyl-phenylamino]-pyrimidin-2-ylamino}-benzonitrile
    • Rilpivirina
    • BDBM222178
    • RILPIVIRINE [USAN]
    • Rilpivirine (JAN/USAN/INN)
    • CHEBI:68606
    • DTXCID90120680
    • RILPIVIRINE [MART.]
    • 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzenecarbonitrile
    • GTPL11387
    • NCGC00319175-03
    • BCP0726000192
    • RILPIVIRINE [VANDF]
    • J05AG05
    • Benzonitrile, 4-((4-((4-((1E)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)-2-pyrimidinyl)amino)-
    • SCHEMBL384696
    • Rilpivirine Z-Isomer HCl
    • Rilpivirine(R 278474, TMC 278)
    • EX-A245
    • RILPIVIRINE (MART.)
    • 4-{[4-({4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
    • Rilpivirine [INN]
    • Q421547
    • Rilpivirine free base
    • AC-30619
    • s7303
    • BENZONITRILE, 4-((4-((4-((1E)-2-CYANOETHENYL)-2,6-DIMETHYLPHENYL)AMINO)-2- PYRIMIDINYL)AMINO)-
    • 4-((4-((4-((E)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile
    • DTXSID10198189
    • SCHEMBL385113
    • AKOS015901680
    • CCG-268241
    • 4-((4-((4-((1E)-2-Cyanoethenyl)-2,6-dimethylphenyl)amino)-2-pyrimidinyl)amino)benzonitrile
    • SW220232-1
    • 4-((4-((4-((1E)-2-CYANOETHENYL)-2,6-DIMETHYLPHENYL)AMINO)PYRIMIDIN-2-YL)AMINO)BENZONITRILE
    • 4-[[4-[4-[(E)-2-cyanovinyl]-2,6-dimethyl-anilino]pyrimidin-2-yl]amino]benzonitrile
    • 4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]-2-pyrimidinyl]amino]benzonitrile
    • Rilpivirine [USAN:INN]
    • CABENUVA COMPONENT RILPIVIRINE
    • RILPIVIRINE COMPONENT OF CABENUVA
    • HSDB 8153
    • RILPIVIRINE [MI]
    • NCGC00319175-08
    • rilpivirinum
    • RILPIVIRINE [WHO-DD]
    • W-202888
    • KE-0036
    • BRD-K06240250-001-01-6
    • Rilpivirine(R 278474, TMC 278)?
    • Rekambys (TN)
    • STL484047
    • 4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile; Edurant; R 278474; Rilpivirine; TMC 278
    • MDL: MFCD11046372
    • 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+
    • InChI Key: YIBOMRUWOWDFLG-ONEGZZNKSA-N
    • SMILES: N(C1C=CN=C(NC2C=CC(C#N)=CC=2)N=1)C1C(C)=CC(/C=C/C#N)=CC=1C

Computed Properties

  • Exact Mass: 366.15900
  • Monoisotopic Mass: 366.159
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 28
  • Rotatable Bond Count: 5
  • Complexity: 607
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 13
  • XLogP3: 4.5
  • Topological Polar Surface Area: 97.4

Experimental Properties

  • Color/Form: No data available
  • Density: 1.27
  • Melting Point: 245 oC
  • Boiling Point: 634.1°C at 760 mmHg
  • Flash Point: 337.3±34.3 °C
  • Refractive Index: 1.665
  • Solubility: 生物體外In Vitro:DMSO溶解度50 mg/mL(136.46 mM;Need ultrasonic)H2O< 0.1 mg/mL(insoluble)
  • PSA: 97.42000
  • LogP: 5.13506

Rilpivirine Security Information

Rilpivirine Customs Data

  • HS CODE:2933599090
  • Customs Data:

    China Customs Code:

    2933599090

    Overview:

    2933599090. Other compounds with pyrimidine ring in structure(Including other compounds with piperazine ring on the structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Rilpivirine Pricemore >>

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Rilpivirine Production Method

Rilpivirine Suppliers

Tiancheng Chemical (Jiangsu) Co., Ltd
Gold Member
Audited Supplier Audited Supplier
(CAS:500287-72-9)利匹韋林
Order Number:LE25955385
Stock Status:in Stock
Quantity:25KG,200KG,1000KG
Purity:99%
Pricing Information Last Updated:Friday, 20 June 2025 12:54
Price ($):discuss personally
Suzhou Senfeida Chemical Co., Ltd
Gold Member
Audited Supplier Audited Supplier
(CAS:500287-72-9)4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
Order Number:sfd17952
Stock Status:in Stock
Quantity:200kg
Purity:99.9%
Pricing Information Last Updated:Friday, 19 July 2024 14:38
Price ($):discuss personally

Additional information on Rilpivirine

Introduction to Rilpivirine (CAS No: 500287-72-9) in Modern Pharmaceutical Research

Rilpivirine, chemically identified by the CAS number 500287-72-9, is a significant compound in the realm of pharmaceutical chemistry, particularly in the development of antiviral medications. As a non-nucleoside reverse transcriptase inhibitor (NNRTI), Rilpivirine has demonstrated remarkable efficacy in the treatment of HIV-1 infection. Its molecular structure, characterized by a pyrrolidinylpyrimidine core, contributes to its unique mechanism of action, which involves the inhibition of viral replication by binding to the reverse transcriptase enzyme. This interaction prevents the conversion of viral RNA into DNA, thereby halting the spread of the virus within the host.

The pharmacological profile of Rilpivirine has been extensively studied and validated through numerous clinical trials. One of the most notable aspects of its development is its high genetic barrier to resistance, which makes it particularly effective in patients who may have developed resistance to other NNRTIs. This resistance profile is attributed to its specific binding interactions with the reverse transcriptase enzyme, which are less prone to mutation compared to other antiviral agents. The compound's ability to maintain efficacy over prolonged periods has made it a cornerstone in combination therapy regimens for HIV-1 infection.

Recent advancements in drug design and molecular modeling have further illuminated the structural and functional properties of Rilpivirine. These studies have revealed that its pyrrolidinylpyrimidine core interacts with key residues in the reverse transcriptase enzyme, such as Tyr215 and Lys101, which are critical for its inhibitory activity. Understanding these interactions has not only enhanced our comprehension of Rilpivirine's mechanism of action but also provided insights into potential drug optimization strategies. For instance, modifications to its structure could improve pharmacokinetic properties or expand its spectrum of activity against other viral strains.

In clinical settings, Rilpivirine is often administered as part of a fixed-dose combination (FDC) pill, which simplifies dosing and improves patient adherence. The FDC formulation typically includes Rilpivirine along with other antiretroviral drugs, such as emtricitabine and tenofovir disoproxil fumarate (TDF). This combination approach leverages the synergistic effects of multiple drugs, reducing the likelihood of viral resistance and improving therapeutic outcomes. The simplicity and effectiveness of these combination therapies have made them a preferred choice for healthcare providers managing HIV-1 infection.

The safety profile of Rilpivirine has been thoroughly evaluated through extensive clinical trials involving diverse patient populations. Common adverse effects associated with its use include nausea, headache, insomnia, and rash. However, these side effects are generally mild and well-tolerated, making Rilpivirine an attractive option for long-term treatment. Importantly, there are no significant drug-drug interactions reported with commonly used medications for other conditions, further enhancing its clinical applicability.

Emerging research has also explored the potential applications of Rilpivirine beyond HIV-1 treatment. Studies suggest that its mechanism of action may be adaptable to other viral infections caused by reverse transcriptase enzymes. For instance, investigations have examined its efficacy against hepatitis B virus (HBV) and certain strains of human papillomavirus (HPV). While further research is needed to validate these findings, they highlight the broad therapeutic potential of Rilpivirine and related compounds.

The development and optimization of Rilpivirine exemplify the progress made in rational drug design and targeted therapy. By leveraging structural biology and computational methods, researchers have been able to fine-tune the pharmacological properties of this compound to maximize its therapeutic benefit while minimizing side effects. This approach underscores the importance of interdisciplinary collaboration between chemists, biologists, and clinicians in advancing pharmaceutical innovation.

Looking ahead, continued research into Rilpivirine and related NNRTIs will likely uncover new insights into viral replication mechanisms and identify novel therapeutic targets. Additionally, advancements in drug delivery systems may enhance the bioavailability and stability of Rilpivirine, further improving patient outcomes. As part of ongoing efforts to combat infectious diseases, compounds like Rilpivirine will remain essential tools in our arsenal against viruses that pose significant public health challenges.

Recommended suppliers
Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:500287-72-9)利匹韋林
LE25955385
Purity:99%
Quantity:25KG,200KG,1000KG
Price ($):Inquiry
Email
Suzhou Senfeida Chemical Co., Ltd
(CAS:500287-72-9)4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile
sfd17952
Purity:99.9%
Quantity:200kg
Price ($):Inquiry
Email