RelatedCAS#:700361-47-3(HCl) 500287-72-9(freebase)  

Synonym:TMC278;TMC278;TMC278;Rilpivirine;Edurant.

IUPAC/ChemicalName:4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile

InChiKey:YIBOMRUWOWDFLG-ONEGZZNKSA-N

InChiCode: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/h4-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+

SMILESCode:N#CC1=CC=C(NC2=NC=CC(NC3=C(C)C=C(/C=C/C#N)C=C3C)=N2)C=C1

TechnicalData

AdditionalInformation

RelatedCAS#
700361-47-3(RilpivirineHCl);
500287-72-9(Rilpivirinefree)

References

1:InstituteforQualityandEfficiencyinHealthCare.Rilpivirine/Emtricitabine/Tenofovir(NewTherapeuticIndication)--BenefitAssessmentAccordingto§35aSocialCodeBookV[Internet].Cologne,Germany:InstituteforQualityandEfficiencyinHealthCare(IQWiG);2014Mar28.Availablefromhttp://www.ncbi.nlm.nih.gov/books/NBK385725/PubMedPMID:27905770.

2:InstituteforQualityandEfficiencyinHealthCare.Rilpivirine--BenefitAssessmentAccordingto§35aSocialCodeBookV[Internet].Cologne,Germany:InstituteforQualityandEfficiencyinHealthCare(IQWiG);2012Apr12.Availablefromhttp://www.ncbi.nlm.nih.gov/books/NBK385641/PubMedPMID:27905736.

3:SaravananS,KausalyaB,GomathiS,SivamalarS,PachamuthuB,PoongulaliS,PradeepA,SunilSS,MothiSN,SmithDM,KantorR.EtravirineandRilpivirinedrugresistanceamongHIV-1subtypeCinfectedChildrenfailingnon-nucleosidereversetranscriptaseinhibitor-basedregimensinSouthIndia.AIDSResHumRetroviruses.2016Nov21.[Epubaheadofprint]PubMedPMID:27869478.

4:DiBiagioA,RiccardiN,TaramassoL,CapettiA,CenderelloG,SignoriA,VitielloP,GuerraM,deSocioGV,CassolaG,QuirinoT,ViscoliC.Switchfromunboostedproteaseinhibitortoasingle-tabletregimencontainingrilpivirineimprovescholesterolandtriglycerides.IntJAntimicrobAgents.2016Nov;48(5):551-554.doi:10.1016/j.ijantimicag.2016.07.009.PubMedPMID:27566908.

5:AouriM,BarceloC,GuidiM,RotgerM,CavassiniM,HizrelC,BuclinT,DecosterdLA,CsajkaC;SwissHIVCohortStudy..PopulationpharmacokineticsandpharmacogeneticsanalysisofRilpivirineinHIV-1infectedindividuals.AntimicrobAgentsChemother.2016Oct31.pii:AAC.00899-16.[Epubaheadofprint]PubMedPMID:27799217.

6:OgbuaguO.Rilpivirine,emtricitabineandtenofoviralafenamide:single-tabletcombinationforthetreatmentofHIV-1infectioninselectedpatients.ExpertRevAntiInfectTher.2016Dec;14(12):1113-1126.PubMedPMID:27797606.

7:LombaardJ,BunupuradahT,FlynnPM,RamapuramJ,SsaliF,CrauwelsH,HoogstoelA,VanEygenV,StevensM.RilpivirineasaTreatmentforHIV-infectedAntiretroviral-naïveAdolescents:Week48Safety,Efficacy,VirologyandPharmacokinetics.PediatrInfectDisJ.2016Nov;35(11):1215-1221.PubMedPMID:27294305.

8:CapettiAF,SterrantinoG,CossuMV,OrofinoG,BarbariniG,DeSocioGV,DiGiambenedettoS,DiBiagioA,CelesiaBM,ArgenteriB,RizzardiniG.SwitchtoDolutegravirplusRilpivirineDualTherapyincART-ExperiencedSubjects:AnObservationalCohort.PLoSOne.2016Oct14;11(10):e0164753.doi:10.1371/journal.pone.0164753.PubMedPMID:27741309;PubMedCentralPMCID:PMC5065232.

9:TroyaJ,RyanP,RiberaE,PodzamczerD,HontañónV,TerrónJA,BoixV,MorenoS,BarrufetP,CastañoM,CarreroA,GalindoMJ,Suárez-LozanoI,KnobelH,RaffoM,SolísJ,YllescasM,EstebanH,González-GarcíaJ,BerenguerJ,ImazA;GESIDA-8314StudyGroup..Abacavir/LamivudineplusRilpivirineIsanEffectiveandSafeStrategyforHIV-1SuppressedPatients:48WeekResultsoftheSIMRIKIRetrospectiveStudy.PLoSOne.2016Oct11;11(10):e0164455.doi:10.1371/journal.pone.0164455.PubMedPMID:27727331;PubMedCentralPMCID:PMC5058546.

10:CollinsSE,GrantPM,UwinkindiF,TalbotA,SeruyangeE,SlamowitzD,MugeniA,RemeraE,NiyonsengaSP,NyirimigaboJ,UwizihiweJP,DongierP,MuhayimpunduR,MazaratiJB,ZolopaA,NsanzimanaS.ARandomizedSwitchFromNevirapine-BasedAntiretroviralTherapytoSingleTabletRilpivirine/Emtricitabine/TenofovirDisoproxilFumarateinVirologicallySuppressedHumanImmunodeficiencyVirus-1-InfectedRwandans.OpenForumInfectDis.2016Jul1;3(3):ofw141.PubMedPMID:27704000;PubMedCentralPMCID:PMC5047400.

11:McGowanI,DezzuttiCS,SiegelA,EngstromJ,NikiforovA,DuffillK,ShetlerC,Richardson-HarmanN,AbebeK,BackD,ElseL,EganD,KhooS,EganJE,StallR,WilliamsPE,RehmanKK,AdlerA,BrandRM,ChenB,AchillesS,CranstonRD.Long-actingrilpivirineaspotentialpre-exposureprophylaxisforHIV-1prevention(theMWRI-01study):anopen-label,phase1,compartmental,pharmacokineticandpharmacodynamicassessment.LancetHIV.2016Dec;3(12):e569-e578.doi:10.1016/S2352-3018(16)30113-8.PubMedPMID:27658864.

12:ParsonsTL,MarzinkeMA.Developmentandvalidationofaliquidchromatographic-tandemmassspectrometricmethodforthemultiplexedquantificationofetravirine,maraviroc,raltegravir,andrilpivirineinhumanplasmaandtissue.JPharmBiomedAnal.2016Nov30;131:333-344.doi:10.1016/j.jpba.2016.08.016.PubMedPMID:27632783.

13:CurranA,RojasJ,CabelloA,TroyaJ,ImazA,DomingoP,MartinezE,RyanP,GórgolasM,PodzamczerD,KnobelH,GutiérrezF,RiberaE.Effectivenessandsafetyofanabacavir/lamivudine + rilpivirineregimenforthetreatmentofHIV-1infectioninnaivepatients.JAntimicrobChemother.2016Dec;71(12):3510-3514.PubMedPMID:27591292.

14:PrathipatiPK,MandalS,DestacheCJ.Simultaneousquantificationoftenofovir,emtricitabine,rilpivirine,elvitegraviranddolutegravirinmouseBIOLOGicalmatricesbyLC-MS/MSanditsapplicationtoapharmacokineticstudy.JPharmBiomedAnal.2016Sep10;129:473-81.doi:10.1016/j.jpba.2016.07.040.PubMedPMID:27497648;PubMedCentralPMCID:PMC5003708.

15:BernaudC,KhatchatourianL,RodallecA,HallN,PerreP,MorrierM,PineauS,JovelinT,André-GarnierE,RaffiF,AllavenaC.OptimizingthevirologicalsuccessoftenofovirDF/FTC/rilpivirineinHIV-infectednaiveandvirologicallysuppressedpatientsthroughstrictclinicalandvirologicalselection.InfectDis(Lond).2016Oct;48(10):754-9.doi:10.1080/23744235.2016.1194528.PubMedPMID:27389932.

16:HayashidaT,HachiyaA,OdeH,NishijimaT,TsuchiyaK,SugiuraW,TakiguchiM,OkaS,GatanagaH.RilpivirineresistancemutationE138KinHIV-1reversetranscriptasepredisposedbyprevalentpolymorphicmutations.JAntimicrobChemother.2016Oct;71(10):2760-6.doi:10.1093/jac/dkw224.PubMedPMID:27330069.

17:Falcon-NeyraL,PallADInoC,NavarroGómezML,Soler-PalacínP,González-ToméMI,DeOrySJ,FrickMA,FortunyC,Noguera-JulianA,MorenoEB,SantosJL,OlbrichP,López-CortésLF,BrizV,NethO;CoRISpeworkinggroup..Off-labeluseofrilpivirineincombinationwithemtricitabineandtenofovirinHIV-1-infectedpediatricpatients:Amulticenterstudy.Medicine(Baltimore).2016Jun;95(24):e3842.doi:10.1097/MD.0000000000003842.PubMedPMID:27310962;PubMedCentralPMCID:PMC4998448.

18:Lambert-NiclotS,AllavenaC,GrudeM,FlandreP,SayonS,AndreE,WirdenM,RodallecA,JovelinT,KatlamaC,CalvezV,RaffiF,MarcelinAG.UsefulnessofanHIVDNAresistancegenotypictestinpatientswhoarecandidatesforaswitchtotherilpivirine/emtricitabine/tenofovirdisoproxilfumaratecombination.JAntimicrobChemother.2016Aug;71(8):2248-51.doi:10.1093/jac/dkw146.PubMedPMID:27231280.

19:NeukamK,EspinosaN,ColladoA,Delgado-FernándezM,Jiménez-AguilarP,Rivero-JuárezA,Hontañón-AntoñanaV,Gómez-BerrocalA,Ruiz-MoralesJ,MerinoD,CarreroA,TéllezF,RíosMJ,Hernández-QueroJ,deLagarde-SebastiánM,Pérez-CamachoI,Vera-MéndezF,MacíasJ,PinedaJA;hEPAticStudyGroup..HepaticSafetyofRilpivirine/Emtricitabine/TenofovirDisoproxilFumarateFixed-DoseSingle-TabletRegimeninHIV-InfectedPatientswithActiveHepatitisCVirusInfection:ThehEPAticStudy.PLoSOne.2016May19;11(5):e0155842.doi:10.1371/journal.pone.0155842.PubMedPMID:27195797;PubMedCentralPMCID:PMC4873169.

20:FocaM,YogevR,WizniaA,HazraR,Jean-PhilippeP,GrahamB,BrittoP,CareyVJ,KingJ,AcostaEP,CresseyTR;IMPAACTP1058ATeam..RilpivirinePharmacokineticsWithoutandWithDarunavir/RitonavirOnceDailyinAdolescentsandYoungAdults.PediatrInfectDisJ.2016Sep;35(9):e271-4.doi:10.1097/INF.0000000000001214.PubMedPMID:27187753.