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.
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.