Rilpivirine

Rilpivirine
Clinical data
Trade names	Edurant, Rekambys, others
Other names	TMC278
AHFS/Drugs.com	Monograph
MedlinePlus	a611037
License data	US DailyMed: Rilpivirine;
Pregnancy; category	AU: B1;
Routes of; administration	By mouth, intramuscular
ATC code	J05AG05 (WHO) ; combinations:; J05AR19 (WHO); J05AR21 (WHO); J05AR08 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	99.7%
Metabolism	CYP3A4
Elimination half-life	tablets: 45 hours; injection: 13–28 weeks
Excretion	85% via faeces, 6% via urine
Identifiers
	IUPAC name 4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile;
CAS Number	500287-72-9 ; as HCl: 700361-47-3;
PubChem CID	6451164; as HCl: 11711114;
DrugBank	DB08864 ; as HCl: DBSALT000152;
ChemSpider	4953643 ; as HCl: 9885836;
UNII	FI96A8X663; as HCl: 212WAX8KDD;
KEGG	D09720; as HCl: D09958;
ChEBI	CHEBI:68606 ; as HCl: CHEBI:68602;
ChEMBL	ChEMBL175691 ; as HCl: ChEMBL1628504;
NIAID ChemDB	169030;
PDB ligand	T27 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID10198189 ;
ECHA InfoCard	100.224.394
Chemical and physical data
Formula	C22H18N6
Molar mass	366.428 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cc1cc(cc(c1Nc2ccnc(n2)Nc3ccc(cc3)C#N)C)/C=C/C#N;
	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+ ; Key:YIBOMRUWOWDFLG-ONEGZZNKSA-N ; ; as HCl: InChI=1S/C22H18N6.ClH/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);1H/b4-3+;; Key:KZVVGZKAVZUACK-BJILWQEISA-N;
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Rilpivirine, sold under the brand name Edurant among others, is a medication, developed by Tibotec, used for the treatment of HIV/AIDS. 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.