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500287-72-9,MFCD11046372
Catalog No.:AA00DB4J

500287-72-9 | Rilpivirine

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1mg
98%
in stock  
$15.00   $11.00
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5mg
98%
in stock  
$26.00   $18.00
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10mg
98%
in stock  
$34.00   $24.00
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25mg
98%(HPLC)
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$43.00   $30.00
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50mg
98%
in stock  
$57.00   $40.00
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100mg
98%
in stock  
$74.00   $52.00
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250mg
98%(HPLC)
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$183.00   $128.00
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1g
98%
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$355.00   $249.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00DB4J
Chemical Name:
Rilpivirine
CAS Number:
500287-72-9
Molecular Formula:
C22H18N6
Molecular Weight:
366.4185
MDL Number:
MFCD11046372
SMILES:
N#C/C=C/c1cc(C)c(c(c1)C)Nc1ccnc(n1)Nc1ccc(cc1)C#N
Properties
Properties
 
Form:
Solid  
MP:
245℃  
Storage:
Light sensitive;Inert atmosphere;-20 ℃;  

Computed Properties
 
Complexity:
607  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
XLogP3:
4.5  

Downstream Synthesis Route
4336-70-3    500293-29-8   
4-4-4-(2-cyanoethenyl)-2,6-dimethylphenylamino-2-pyrimidinylaminobenzonitrile 
  500287-72-9 

[1]JournalofMedicinalChemistry,2005,vol.48,p.2072-2079

[2]Patent:US9192577,2015,B2.Locationinpatent:Page/Pagecolumn73-74

107-13-1    374067-85-3   
4-4-4-(2-cyanoethenyl)-2,6-dimethylphenylamino-2-pyrimidinylaminobenzonitrile 
  500287-72-9 

[1]JournalofMedicinalChemistry,2005,vol.48,p.2072-2079

[2]Patent:WO2004/16581,2004,A1.Locationinpatent:Page24

[3]Patent:US9192577,2015,B2.Locationinpatent:Page/Pagecolumn67-68

[1]JournalofMedicinalChemistry,2005,vol.48,p.2072-2079

[2]Patent:US9192577,2015,B2

[1]JournalofMedicinalChemistry,2005,vol.48,p.2072-2079

[1]JournalofMedicinalChemistry,2005,vol.48,p.2072-2079

[2]JournalofMedicinalChemistry,2005,vol.48,p.2072-2079

[3]Patent:WO2013/179105,2013,A1

Literature

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Journal: Antimicrobial agents and chemotherapy 20140401

Title: Discovery of 2-pyridone derivatives as potent HIV-1 NNRTIs using molecular hybridization based on crystallographic overlays.

Journal: Bioorganic & medicinal chemistry 20140315

Title: In vitro characterization of MK-1439, a novel HIV-1 nonnucleoside reverse transcriptase inhibitor.

Journal: Antimicrobial agents and chemotherapy 20140301

Title: Discovery of MK-1439, an orally bioavailable non-nucleoside reverse transcriptase inhibitor potent against a wide range of resistant mutant HIV viruses.

Journal: Bioorganic & medicinal chemistry letters 20140201

Title: In vitro and in vivo activities of AIC292, a novel HIV-1 nonnucleoside reverse transcriptase inhibitor.

Journal: Antimicrobial agents and chemotherapy 20131101

Title: Optimization of diarylazines as anti-HIV agents with dramatically enhanced solubility.

Journal: Bioorganic & medicinal chemistry letters 20130915

Title: Update on rilpivirine: a new potent non-nucleoside reverse transcriptase inhibitor (NNRTI) of HIV replication.

Journal: Annals of medicine 20130501

Title: Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro.

Journal: International journal of antimicrobial agents 20130501

Title: Rational design of potent non-nucleoside inhibitors of HIV-1 reverse transcriptase.

Journal: Journal of medicinal chemistry 20121213

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Journal: The Journal of biological chemistry 20121102

Title: Minority variants associated with resistance to HIV-1 nonnucleoside reverse transcriptase inhibitors during primary infection.

Journal: Journal of clinical virology : the official publication of the Pan American Society for Clinical Virology 20121001

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Journal: Clinical drug investigation 20121001

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Journal: AIDS (London, England) 20120824

Title: Design, synthesis, and preclinical evaluations of novel 4-substituted 1,5-diarylanilines as potent HIV-1 non-nucleoside reverse transcriptase inhibitor (NNRTI) drug candidates.

Journal: Journal of medicinal chemistry 20120823

Title: Synthesis of betulinic acid derivatives as entry inhibitors against HIV-1 and bevirimat-resistant HIV-1 variants.

Journal: Bioorganic & medicinal chemistry letters 20120815

Title: Effect of gender and race on the week 48 findings in treatment-naïve, HIV-1-infected patients enrolled in the randomized, phase III trials ECHO and THRIVE.

Journal: HIV medicine 20120801

Title: Where rilpivirine meets with tenofovir, the start of a new anti-HIV drug combination era.

Journal: Biochemical pharmacology 20120801

Title: Efficacy and safety of rilpivirine in treatment-naive, HIV-1-infected patients with hepatitis B virus/hepatitis C virus coinfection enrolled in the Phase III randomized, double-blind ECHO and THRIVE trials.

Journal: The Journal of antimicrobial chemotherapy 20120801

Title: New drugs 2012, part 2.

Journal: Nursing 20120701

Title: Baseline E138 reverse transcriptase resistance-associated mutations in antiretroviral-naive HIV-infected patients.

Journal: AIDS (London, England) 20120601

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Journal: American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20120515

Title: Long-term efficacy, safety, and tolerability of rilpivirine (RPV, TMC278) in HIV type 1-infected antiretroviral-naive patients: week 192 results from a phase IIb randomized trial.

Journal: AIDS research and human retroviruses 20120501

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Journal: Expert opinion on pharmacotherapy 20120501

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Journal: Bioorganic & medicinal chemistry letters 20120401

Title: Rilpivirine.

Journal: Drugs 20120305

Title: Prevalence of TMC278 (rilpivirine) associated mutations in the Frankfurt Resistance Database.

Journal: Journal of clinical virology : the official publication of the Pan American Society for Clinical Virology 20120301

Title: The HIV-1 reverse transcriptase M184I mutation enhances the E138K-associated resistance to rilpivirine and decreases viral fitness.

Journal: Journal of acquired immune deficiency syndromes (1999) 20120101

Title: Genotypic and phenotypic characterization of HIV-1 isolates obtained from patients on rilpivirine therapy experiencing virologic failure in the phase 3 ECHO and THRIVE studies: 48-week analysis.

Journal: Journal of acquired immune deficiency syndromes (1999) 20120101

Title: Boceprevir, telaprevir, and rilpivirine hydrochloride.

Journal: Journal of the American Pharmacists Association : JAPhA 20120101

Title: Pharmacokinetic parameters of once-daily rilpivirine following administration of efavirenz in healthy subjects.

Journal: Antiviral therapy 20120101

Title: Computationally-guided optimization of a docking hit to yield catechol diethers as potent anti-HIV agents.

Journal: Journal of medicinal chemistry 20111222

Title: Design and synthesis of pyridone inhibitors of non-nucleoside reverse transcriptase.

Journal: Bioorganic & medicinal chemistry letters 20111215

Title: Update of the past year: a review from IDSA 2011.

Journal: Topics in antiviral medicine 20111201

Title: Role of non-nucleoside reverse transcriptase inhibitors in treating HIV-infected children.

Journal: Drugs 20111112

Title: FDA notifications. Complera approved.

Journal: AIDS alert 20111101

Title: Rilpivirine (Edurant)--a new drug for HIV infection.

Journal: The Medical letter on drugs and therapeutics 20110822

Title: HIV/AIDS and the road to Rome.

Journal: Lancet (London, England) 20110716

Title: Rilpivirine: a step forward in tailored HIV treatment.

Journal: Lancet (London, England) 20110716

Title: Rilpivirine versus efavirenz with two background nucleoside or nucleotide reverse transcriptase inhibitors in treatment-naive adults infected with HIV-1 (THRIVE): a phase 3, randomised, non-inferiority trial.

Journal: Lancet (London, England) 20110716

Title: Rilpivirine versus efavirenz with tenofovir and emtricitabine in treatment-naive adults infected with HIV-1 (ECHO): a phase 3 randomised double-blind active-controlled trial.

Journal: Lancet (London, England) 20110716

Title: Synthesis, activity, and structural analysis of novel α-hydroxytropolone inhibitors of human immunodeficiency virus reverse transcriptase-associated ribonuclease H.

Journal: Journal of medicinal chemistry 20110714

Title: Rilpivirine: a new addition to the anti-HIV-1 armamentarium.

Journal: Drugs of today (Barcelona, Spain : 1998) 20110101

Title: Etravirine and rilpivirine resistance in HIV-1 subtype CRF01_AE-infected adults failing non-nucleoside reverse transcriptase inhibitor-based regimens.

Journal: Antiviral therapy 20110101

Title: Rilpivirine and complera: new first-line treatment options.

Journal: BETA : bulletin of experimental treatments for AIDS : a publication of the San Francisco AIDS Foundation 20110101

Title: Looking for an active conformation of the future HIV type-1 non-nucleoside reverse transcriptase inhibitors.

Journal: Antiviral chemistry & chemotherapy 20100811

Title: Validation of a rapid and sensitive high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) assay for the simultaneous determination of existing and new antiretroviral compounds.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100601

Title: Bioequivalent formulation for the fixed-dose regimen of Truvada and TMC278 finalized.

Journal: AIDS patient care and STDs 20100601

Title: Crystal structures of HIV-1 reverse transcriptase with etravirine (TMC125) and rilpivirine (TMC278): implications for drug design.

Journal: Journal of medicinal chemistry 20100527

Title: Conformational populations of ligand-sized molecules by replica exchange molecular dynamics and temperature reweighting.

Journal: Journal of computational chemistry 20100501

Title: TMC278, a next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI), active against wild-type and NNRTI-resistant HIV-1.

Journal: Antimicrobial agents and chemotherapy 20100201

Title: [Discovery and development of diarylpyrimidines (DAPYs) as next-generation HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs)].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20100201

Title: Efficacy and safety of TMC278 in antiretroviral-naive HIV-1 patients: week 96 results of a phase IIb randomized trial.

Journal: AIDS (London, England) 20100102

Title: Drug interactions with new and investigational antiretrovirals.

Journal: Clinical pharmacokinetics 20100101

Title: Molecular dynamics study of non-nucleoside reverse transcriptase inhibitor 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile (TMC278/rilpivirine) aggregates: correlation between amphiphilic properties of the drug and oral bioavailability.

Journal: Journal of medicinal chemistry 20091008

Title: Discovery of diarylpyridine derivatives as novel non-nucleoside HIV-1 reverse transcriptase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20090915

Title: Development of a long-acting injectable formulation with nanoparticles of rilpivirine (TMC278) for HIV treatment.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20090801

Title: Second complete once-daily single tablet therapy in development.

Journal: AIDS patient care and STDs 20090801

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Journal: Pharmacotherapy 20090301

Title: Development of a liquid chromatographic assay for an anti-HIV tablet containing lamivudine, zidovudine and TMC278.HCL.

Journal: Journal of pharmaceutical and biomedical analysis 20090220

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Journal: Antiviral therapy 20090101

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Journal: AIDS patient care and STDs 20081001

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Journal: Current opinion in investigational drugs (London, England : 2000) 20080801

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Journal: Current opinion in drug discovery & development 20080701

Title: New drugs.

Journal: Journal of HIV therapy 20080601

Title: Synthesis of novel diarylpyrimidine analogues of TMC278 and their antiviral activity against HIV-1 wild-type and mutant strains.

Journal: European journal of medicinal chemistry 20070501

Title: NNRTI data in naive patients.

Journal: AIDS patient care and STDs 20070401

Title: Short-term antiviral activity of TMC278--a novel NNRTI--in treatment-naive HIV-1-infected subjects.

Journal: AIDS (London, England) 20060822

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Journal: Current opinion in investigational drugs (London, England : 2000) 20060201

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Journal: MMW Fortschritte der Medizin 20050425

Title: In search of a novel anti-HIV drug: multidisciplinary coordination in the discovery of 4-[[4-[[4-[(1E)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2- pyrimidinyl]amino]benzonitrile (R278474, rilpivirine).

Journal: Journal of medicinal chemistry 20050324

Title: Synthesis of novel diarylpyrimidine analogues and their antiviral activity against human immunodeficiency virus type 1.

Journal: Journal of medicinal chemistry 20050324

Title: A series of diaryltriazines and diarylpyrimidines are highly potent nonnucleoside reverse transcriptase inhibitors with possible applications as microbicides.

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Title: Janssen PAJ, et, al. In search of a novel anti-HIV drug: multidisciplinary coordination in the discovery of 4-[-[-[(1E)-2-cyanoethenyl-2,6-dimethylphenylamino-2- pyrimidinylaminobenzonitrile (R278474, rilpivirine). J Med Chem. 2005 Mar 24;48(6):1901-9.

Title: Azijn H, et, al. TMC278, a next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI), active against wild-type and NNRTI-resistant HIV-1. Antimicrob Agents Chemother. 2010 Feb;54(2):718-27.

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