Structure via PubChem · Public domain (PubChem)
rilpivirine
Sign in to saveAlso known as TMC-278, R-278474, TMC278, TMC 278, 4-{[4-({4-[(e)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile, RPV
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.
In the Vinony graph
Within Vinony's link graph, rilpivirine is referenced by 197 other articles, and connects out to tenofovir alafenamide, reverse-transcriptase inhibitor and HIV.
It is catalogued under topics including Chemical articles with multiple CAS registry numbers, Chemical articles with multiple ChEBIs and Chemical articles with multiple PubChem CIDs.
Its subject is documented across 19 Wikipedia language editions.
Key facts
- Drug.PDB_ligand
- T27
- Drug.synonyms
- TMC278
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 417509820
- Drug.image
- Rilpivirine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 180
- Drug.image2
- Rilpivirine 3D 2zd1.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Edurant, Rekambys, others
- Drug.MedlinePlus
- a611037
- Drug.DailyMedID
- Rilpivirine
- Drug.pregnancy_AU
- B1
- Drug.routes_of_administration
- By mouth, intramuscular
- Drug.ATC_prefix
- J05
- Drug.ATC_suffix
- AG05
- Drug.ATC_supplemental
- combinations:
via Wikipedia infobox
Chemical data
- Formula
- C22H18N6
- Molecular weight
- 366.4 g/mol
- IUPAC name
- 4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile
- SMILES
- CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)/C=C/C#N
- InChIKey
- YIBOMRUWOWDFLG-ONEGZZNKSA-N
- XLogP
- 4.5
- Polar surface area
- 97.4 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2011
- Admin. routes
- oral, parenteral
- Indications
- HIV-1 infection, HIV infection, hepatitis C virus infection, AIDS
via ChEMBL · EBI
Research
1,480 papers- Long-Acting Cabotegravir and Rilpivirine after Oral Induction for HIV-1 Infection.The New England journal of medicine · 2020
- Dolutegravir-rilpivirine coformulation.Current opinion in HIV and AIDS · 2018
- Cabotegravir/Rilpivirine: the last FDA-approved drug to treat HIV.Expert review of anti-infective therapy · 2022
- Rilpivirine.Drugs · 2012
- Cabotegravir Plus Rilpivirine: First Approval.Drugs · 2020
via PubMed
Wikidata facts
- Mass
- 366.159
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₂H₁₈N₆
- canonical SMILES
- CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)C=CC#N
- isomeric SMILES
- CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)/C=C/C#N
- World Health Organisation international non-proprietary name
- rilpivirine
- subject has role
- reverse-transcriptase inhibitor
- defined daily dose
- 25
- Commons category
- Rilpivirine
via Wikidata · CC0
~9 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Available forms
- Contraindications and interactions
- Adverse effects
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Fixed-dose combinations
- Chemistry
- History
- References
{{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 417509820 | image = Rilpivirine.svg | image_class = skin-invert-image | width = 180 | alt = | image2 = Rilpivirine 3D 2zd1.png | image_class2 = bg-transparent | alt2 =
| tradename = Edurant, Rekambys, others | Drugs.com = | MedlinePlus = a611037 | DailyMedID = Rilpivirine | pregnancy_AU = B1 | pregnancy_category = | routes_of_administration = By mouth, intramuscular | ATC_prefix = J05 | ATC_suffix = AG05 | ATC_supplemental = combinations:
Excerpted from Wikipedia’s “rilpivirine” article, available under the CC BY-SA 4.0 licence.