Rilpivirine

Rilpivirine

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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 category	US: B (No risk in non-human studies)
Legal status	US: ℞-only
Routes of administration	Oral
Pharmacokinetic data
Biological half-life	38 hours
Identifiers
CAS Number	500287-72-9 Y
ATC code	J05AG05 (WHO)
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
Molecular mass	366.42 g/mol
InChI 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+ N Key:YIBOMRUWOWDFLG-ONEGZZNKSA-N N
NY (what is this?)  (verify)

Rilpivirine (TMC278, trade name Edurant) is a pharmaceutical drug, developed by Tibotec, for the treatment of HIV infection. 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.

Rilpivirine entered phase III clinical trials in April 2008, and was approved for use in the United States in May 2011. 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; it was licensed in the European Union under the brand name Eviplera in November 2011.

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.