Rilpivirine

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Rilpivirine
Rilpivirine.svg
Rilpivirine 3D 2zd1.png
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
ChEBI CHEBI:68606 N
ChEMBL CHEMBL175691 N
NIAID ChemDB 169030
PDB ligand ID T27 (PDBe, RCSB PDB)
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). Rilpivirine in combination with emtricitabine and tenofovir has been shown to have higher rates of virologic failure than Atripla in patients with baseline HIV viral loads greater than 100,000 copies/mm3.


References[edit]

  1. ^ "TMC278 — A new NNRTI". Tibotec. 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. 
  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.". 14th Conference on Retroviruses and Opportunistic Infections. Archived from the original on October 19, 2007. 
  5. ^ "A Clinical Trial in Treatment naïve HIV-1 Patients Comparing TMC278 to Efavirenz in Combination With Tenofovir + Emtricitabine". ClinicalTrials.gov. National Institutes of Health. October 25, 2012. Retrieved January 1, 2014. 
  6. ^ "A Clinical Trial in Treatment naïve HIV-Subjects Patients Comparing TMC278 to Efavirenz in Combination With 2 Nucleoside/Nucleotide Reverse Transcriptase Inhibitors". ClinicalTrials.gov. National Institutes of Health. May 14, 2012. Retrieved January 1, 2014. 
  7. ^ "FDA approves new HIV treatment". U.S. Food and Drug Administration. Retrieved 2011-05-20. 
  8. ^ "Approval of Complera: emtricitabine/rilpivirine/tenofovir DF fixed dose combination". U.S. Food and Drug Administration. August 10, 2011.