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;
	(what is this?) (verify)

Rilpivirine, sold under the brand name Edurant among others, is a medication, developed by Tibotec, used for the treatment of HIV/AIDS.^[6]^[7] 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.^[8]^[9]

^ "Edurant Product information". Health Canada. 9 September 2014. Retrieved 17 February 2025.
^ "Edurant 25 mg tablets - Summary of Product Characteristics (SmPC)". (emc). 21 January 2020. Retrieved 4 January 2021.
^ "Edurant- rilpivirine hydrochloride tablet, film coated". DailyMed. Retrieved 4 January 2021.
^ "Edurant EPAR". European Medicines Agency (EMA). 12 December 2011. Retrieved 4 January 2021.
^ Cite error: The named reference Rekambys EPAR was invoked but never defined (see the help page).
^ "TMC278 — A new NNRTI". Tibotec. Archived from the original on 20 December 2008. Retrieved 7 March 2010.
^ Stellbrink HJ (October 2007). "Antiviral drugs in the treatment of AIDS: what is in the pipeline ?". European Journal of Medical Research. 12 (9): 483–495. PMID 17933730.
^ Goebel F, Yakovlev A, Pozniak AL, Vinogradova E, Boogaerts G, Hoetelmans R, et al. (August 2006). "Short-term antiviral activity of TMC278--a novel NNRTI--in treatment-naive HIV-1-infected subjects". AIDS. 20 (13): 1721–1726. doi:10.1097/01.aids.0000242818.65215.bd. PMID 16931936. S2CID 26078073.{{cite journal}}: CS1 maint: overridden setting (link)
^ 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 19 October 2007.

[1] "Edurant Product information". Health Canada. 9 September 2014. Retrieved 17 February 2025.

[2] "Edurant 25 mg tablets - Summary of Product Characteristics (SmPC)". (emc). 21 January 2020. Retrieved 4 January 2021.

[Edurant_FDA_label-3] "Edurant- rilpivirine hydrochloride tablet, film coated". DailyMed. Retrieved 4 January 2021.

[4] "Edurant EPAR". European Medicines Agency (EMA). 12 December 2011. Retrieved 4 January 2021.

[Rekambys_EPAR-5] Cite error: The named reference Rekambys EPAR was invoked but never defined (see the help page).

[6] "TMC278 — A new NNRTI". Tibotec. Archived from the original on 20 December 2008. Retrieved 7 March 2010.

[pmid17933730-7] Stellbrink HJ (October 2007). "Antiviral drugs in the treatment of AIDS: what is in the pipeline ?". European Journal of Medical Research. 12 (9): 483–495. PMID 17933730.

[8] Goebel F, Yakovlev A, Pozniak AL, Vinogradova E, Boogaerts G, Hoetelmans R, et al. (August 2006). "Short-term antiviral activity of TMC278--a novel NNRTI--in treatment-naive HIV-1-infected subjects". AIDS. 20 (13): 1721–1726. doi:10.1097/01.aids.0000242818.65215.bd. PMID 16931936. S2CID 26078073.{{cite journal}}: CS1 maint: overridden setting (link)

[9] 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 19 October 2007.

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