Rilpivirine

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Rilpivirine
Systematic (IUPAC) name
4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
Clinical data
Trade names Edurant
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a611037
Licence data US FDA:link
Pregnancy cat. B (US)
Legal status -only (US)
Routes Oral
Pharmacokinetic data
Half-life 38 hours
Identifiers
CAS number 500287-72-9 YesY
ATC code J05AG05
PubChem CID 6451164
ChemSpider 4953643 N
UNII FI96A8X663 N
ChEMBL CHEMBL175691 N
NIAID ChemDB 169030
Chemical data
Formula C22H18N6 
Mol. mass 366.42 g/mol
 N (what is this?)  (verify)

Rilpivirine (TMC278, trade name Edurant) is a pharmaceutical drug, developed by Tibotec, for the treatment of HIV infection.[1][2] It is a second-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) with higher potency, longer half-life and reduced side-effect profile compared with older NNRTIs, such as efavirenz.[3][4]

Rilpivirine entered phase III clinical trials in April 2008,[5][6] and was approved for use in the United States in May 2011.[7] A fixed-dose drug combining rilpivirine with emtricitabine and tenofovir, was approved by the U.S. Food and Drug Administration in August 2011 under the brand name Complera.[8]

Like etravirine, a second-generation NNRTI approved in 2008, rilpivirine is a diarylpyrimidine (DAPY).

[edit] References

  1. ^ "TMC278 - A new NNRTI". Tibotec. http://www.tibotec.com/bgdisplay.jhtml?itemname=HIV_tmc278. Retrieved 2010-03-07. 
  2. ^ Stellbrink HJ (2007). "Antiviral drugs in the treatment of AIDS: what is in the pipeline ?". Eur. J. Med. Res. 12 (9): 483–95. PMID 17933730. 
  3. ^ Goebel F, Yakovlev A, Pozniak AL, Vinogradova E, Boogaerts G, Hoetelmans R, de Béthune MP, Peeters M, Woodfall B (2006). "Short-term antiviral activity of TMC278--a novel NNRTI--in treatment-naive HIV-1-infected subjects". AIDS 20 (13): 1721–6. doi:10.1097/01.aids.0000242818.65215.bd. PMID 16931936. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?an=00002030-200608220-00005. 
  4. ^ Pozniak A, Morales-Ramirez J, Mohap L et al. 48-Week Primary Analysis of Trial TMC278-C204: TMC278 Demonstrates Potent and Sustained Efficacy in ART-naïve Patients. Oral abstract 144LB.
  5. ^ ClinicalTrials.gov A Clinical Trial in Treatment naïve HIV-1 Patients Comparing TMC278 to Efavirenz in Combination With Tenofovir + Emtricitabine
  6. ^ ClinicalTrials.gov A Clinical Trial in Treatment naïve HIV-Subjects Patients Comparing TMC278 to Efavirenz in Combination With 2 Nucleoside/Nucleotide Reverse Transcriptase Inhibitors
  7. ^ "FDA approves new HIV treatment". FDA. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm256087.htm. Retrieved 2011-05-20. 
  8. ^ "Approval of Complera: emtricitabine/rilpivirine/tenofovir DF fixed dose combination". FDA. August 10, 2011. http://www.fda.gov/ForConsumers/ByAudience/ForPatientAdvocates/HIVandAIDSActivities/ucm267592.htm. 
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