Identification
- Summary
Rilpivirine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used in combination with other antiretrovirals to specifically treat human immunodeficiency virus type 1 (HIV-1).
- Brand Names
- Complera, Edurant, Juluca, Odefsey
- Generic Name
- Rilpivirine
- DrugBank Accession Number
- DB08864
- Background
Rilpivirine is non-nucleoside reverse transcriptase inhibitor (NNRTI) which is used for the treatment of HIV-1 infections in treatment-naive patients.1 It is a diarylpyrimidine derivative.2 The internal conformational flexibility of rilpivirine and the plasticity of it interacting binding site gives it a very high potency and reduces the chance of resistance compared to other NNRTI's.3 Rilpivirine was developed by Tilbotec, Inc. and FDA approved on May 20, 2011.6 On November 21, 2017, Rilpivirine, in combination with dolutegravir, was approved as part of the first complete treatment regimen with only two drugs for the treatment of adults with HIV-1 named Juluca.7 Rilpivirine in combination with cabotegravir was granted FDA approval on 21 January 2021.10 While previously administered once-monthly only, this combination product was granted FDA approval for dosing every two months on February 01, 2022 11 and without the need for an oral lead-in period prior.10
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Rilpivirine (DB08864)
- Weight
- Average: 366.4185
Monoisotopic: 366.159294606 - Chemical Formula
- C22H18N6
- Synonyms
- 4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
- Rilpivirina
- Rilpivirine
- External IDs
- R 278474
- R-278474
- R278474
- TMC 278
- TMC-278
- TMC278
Pharmacology
- Indication
Rilpivirine, in combination with other agents, is indicated for the treatment of HIV-1 infections in antiretroviral treatment-naive patients with HIV-1 RNA ≤100,000 copies/mL and CD4+ cell count >200 cells/mm3.6 The FDA combination therapy approval of rilpivirine and dolutegravir is indicated for adults and adolescents 12 years of age and older weighing at least 35 kg with HIV-1 infections whose virus is currently suppressed (< 50 copies/ml) on a stable regimen for at least six months, without a history of treatment failure and no known substitutions associated to resistance to any of the two components of the therapy.7
Rilpivirine in combination with cabotegravir is indicated as a complete regimen for the treatment of HIV-1 infection in adults and adolescents - ≥12 years old and weighing at least 35kg - to replace the current antiretroviral regimen in those who are virologically suppressed (HIV-1 RNA <50 copies/mL) on a stable antiretroviral regimen with no history of treatment failure and with no known or suspected resistance to either cabotegravir or rilpivirine.10
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Hiv-1 infection •••••••••••• ••••• ••• •••• •••• •• ••••• •• ••••••• •••••••••• •••••••••••••••• •••••• •• ••••• •• •• •••••• Used in combination to treat Human immunodeficiency virus type 1 (hiv-1) Combination Product in combination with: Dolutegravir (DB08930) •••••••••••• ••••• ••• ••••• •••• ••••••••••••• •••••• •••••••••••••• •••••••• •• ••••••• •• ••••••••• ••••••• •••••• Used in combination to treat Human immunodeficiency virus type 1 (hiv-1) Combination Product in combination with: Cabotegravir (DB11751) •••••••••••• ••••••••••• ••••• •• ••••••• •• ••••••••• •••••••• •••••••••••••••••••••••• •••••• •• ••••• •• •• - Contraindications & Blackbox Warnings
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Rilpivirine is a non-nucleoside reverse transcriptase inhibitor that inhibits the replication of HIV-1.9 It has a long duration of action as the oral tablet is given daily and the intramuscular suspension is given monthly.9,10 Patients should be counselled regarding the risk of hypersensitivity reactions, hepatotoxicity, depressive disorders, and the redistribution or accumulation of body fat.9
- Mechanism of action
Rilpivirine is a non-competitive NNRTI that binds to reverse transcriptase.9 Its binding results in the blockage of RNA and DNA- dependent DNA polymerase activities, like HIV-1 replication. It does not present activity against human DNA polymerases α, β and γ.8,9 Rilpivirine's flexible structure around the aromatic rings allows the adaptation to changes in the non-nucleoside RT binding pocket, reducing the likelihood of viral mutations conferring resistance.4
Target Actions Organism AReverse transcriptase/RNaseH inhibitorHuman immunodeficiency virus 1 UNuclear receptor subfamily 1 group I member 2 agonistHumans - Absorption
Rilpivirine has a Tmax of 3-4 hours and has a mean AUC of 2235 ± 851 ng*h/mL.3,9 A 25mg dose reaches a Cmax of 247 ng/mL in healthy subjects and 138.6 ng/mL in patients with HIV-1.8
- Volume of distribution
In HIV-1 patients, the apparent volume of distribution in the central compartment was 152-173 L.8
- Protein binding
Rilpivirine is >99% bound to plasma protein, most commonly albumin.3,9
- Metabolism
Rilpivirine is predominantly metabolized by CYP3A4 and CYP3A5 to the hydroxylated metabolites M1, M2, M3, and M4.5,9 UGT1A1 glucuronidates the M2 metabolite to form M6, UGT1A4 glucuronidates rilpivirine to form M5, and an unknown UGT glucuronidates the M4 metabolite to form M7.5
Hover over products below to view reaction partners
- Route of elimination
Rilpivirine is 85% eliminated in the feces and 6.1% eliminated in the urine.9 25% of a dose is recovered in the feces as the unchanged parent drug, while <1% of a dose is recovered in the urine as the unchanged parent drug.9
- Half-life
Rilpivirine has a terminal half-life of 34-55 hours.3
- Clearance
In HIV-1 patients, the apparent total clearance is estimated to be 6.89-8.66 L/h.8
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
In the event of an overdose, contact a poison control centre.9 Patients should be treated with symptomatic and supportive measures, including monitoring of the QT interval.9 Dialysis is not expected to remove significant amounts of the drug from plasma as it is highly bound to albumin.9
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Rilpivirine can be increased when it is combined with Abametapir. Abatacept The metabolism of Rilpivirine can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Rilpivirine. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Rilpivirine. Acalabrutinib The serum concentration of Rilpivirine can be increased when it is combined with Acalabrutinib. - Food Interactions
- Avoid St. John's Wort. St.John's Wort will decrease levels of this medication.
- Take with food. Absorption is increased by 40% if taken with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Rilpivirine hydrochloride 212WAX8KDD 700361-47-3 KZVVGZKAVZUACK-BJILWQEISA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Edurant Tablet, film coated 25 mg/1 Oral Janssen Products, LP 2011-05-20 Not applicable US 
Edurant Tablet, film coated 25 mg Oral Janssen Cilag International Nv 2016-09-08 Not applicable EU 
Edurant Tablet 25 mg Oral Janssen Pharmaceuticals 2011-08-31 Not applicable Canada 
Rekambys Injection 900 mg Intramuscular Janssen Cilag International Nv 2021-01-12 Not applicable EU Rekambys Injection 600 mg Intramuscular Janssen Cilag International Nv 2021-01-12 Not applicable EU - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Cabenuva Rilpivirine (300 mg / mL) + Cabotegravir (200 mg / mL) Kit; Suspension, extended release Intramuscular ViiV Healthcare ULC 2020-09-21 Not applicable Canada Cabenuva Rilpivirine (300 mg / mL) + Cabotegravir (200 mg / mL) Kit; Suspension, extended release Intramuscular ViiV Healthcare ULC 2020-09-21 Not applicable Canada Cabenuva Rilpivirine (300 mg/1mL) + Cabotegravir (200 mg/1mL) Injection, suspension, extended release; Kit Intramuscular ViiV Healthcare Company 2021-01-21 Not applicable US Cabenuva Rilpivirine (300 mg/1mL) + Cabotegravir (200 mg/1mL) Injection, suspension, extended release; Kit Intramuscular ViiV Healthcare Company 2021-01-21 Not applicable US Complera Rilpivirine hydrochloride (25 mg) + Emtricitabine (200 mg) + Tenofovir disoproxil fumarate (300 mg) Tablet Oral Gilead Sciences 2011-10-20 Not applicable Canada
Categories
- ATC Codes
- J05AR19 — Emtricitabine, tenofovir alafenamide and rilpivirine
- J05AR — Antivirals for treatment of HIV infections, combinations
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J05AR — Antivirals for treatment of HIV infections, combinations
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J05AR — Antivirals for treatment of HIV infections, combinations
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Anti-HIV Agents
- Anti-Infective Agents
- Anti-Retroviral Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Antivirals used in combination for the treatment of HIV infections
- BCRP/ABCG2 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors
- Cytochrome P-450 CYP2B6 Inhibitors (strong)
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (weak)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Direct Acting Antivirals
- Enzyme Inhibitors
- Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor
- Nitriles
- Non-Nucleoside Reverse Transcriptase Inhibitors
- Nonnucleoside Reverse Transcriptase Inhibitors
- Nucleic Acid Synthesis Inhibitors
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inhibitors
- P-glycoprotein inhibitors
- Potential QTc-Prolonging Agents
- Pyrimidines
- QTc Prolonging Agents
- Reverse Transcriptase Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzonitriles
- Direct Parent
- Benzonitriles
- Alternative Parents
- m-Xylenes / Styrenes / Aniline and substituted anilines / Aminopyrimidines and derivatives / Imidolactams / Hydropyrimidines / Heteroaromatic compounds / Secondary amines / Nitriles / Azacyclic compounds show 2 more
- Substituents
- Amine / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzonitrile / Carbonitrile / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine show 11 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- aminopyrimidine, nitrile (CHEBI:68606)
- Affected organisms
- Humans and other mammals
- Human Immunodeficiency Virus
Chemical Identifiers
- UNII
- FI96A8X663
- CAS number
- 500287-72-9
- InChI Key
- YIBOMRUWOWDFLG-ONEGZZNKSA-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+
- IUPAC Name
- 4-{[4-({4-[(1E)-2-cyanoeth-1-en-1-yl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
- SMILES
- CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC2=CC=C(C=C2)C#N)=N1
References
- General References
- Putcharoen O, Kerr SJ, Ruxrungtham K: An update on clinical utility of rilpivirine in the management of HIV infection in treatment-naive patients. HIV AIDS (Auckl). 2013 Sep 16;5:231-41. doi: 10.2147/HIV.S25712. [Article]
- Usach I, Melis V, Peris JE: Non-nucleoside reverse transcriptase inhibitors: a review on pharmacokinetics, pharmacodynamics, safety and tolerability. J Int AIDS Soc. 2013 Sep 4;16:1-14. doi: 10.7448/IAS.16.1.18567. [Article]
- Ford N, Lee J, Andrieux-Meyer I, Calmy A: Safety, efficacy, and pharmacokinetics of rilpivirine: systematic review with an emphasis on resource-limited settings. HIV AIDS (Auckl). 2011;3:35-44. doi: 10.2147/HIV.S14559. Epub 2011 Apr 28. [Article]
- Azijn H, Tirry I, Vingerhoets J, de Bethune MP, Kraus G, Boven K, Jochmans D, Van Craenenbroeck E, Picchio G, Rimsky LT: TMC278, a next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI), active against wild-type and NNRTI-resistant HIV-1. Antimicrob Agents Chemother. 2010 Feb;54(2):718-27. doi: 10.1128/AAC.00986-09. Epub 2009 Nov 23. [Article]
- Lade JM, Avery LB, Bumpus NN: Human biotransformation of the nonnucleoside reverse transcriptase inhibitor rilpivirine and a cross-species metabolism comparison. Antimicrob Agents Chemother. 2013 Oct;57(10):5067-79. doi: 10.1128/AAC.01401-13. Epub 2013 Aug 5. [Article]
- J&J News [Link]
- FDA News and Events [Link]
- Australian Government: Australian Public Assessment Report for Rilpivirine [Link]
- FDA Approved Drug Products: Edurant (rilpivirine) oral tablets [Link]
- FDA Approved Drug Products: Cabenuva (Cabotegravir and Rilpivirine) Intramuscular Extended-Release Suspension [Link]
- BioSpace News: ViiV Healthcare Announces US FDA Approval of Cabenuva (cabotegravir, rilpivirine) for Use Every Two Months, Expanding the Label of the First and Only Complete Long-Acting HIV Treatment [Link]
- FDA Approved Drug Products: JULUCA (dolutegravir and rilpivirine tablets), for oral use [Link]
- External Links
- Human Metabolome Database
- HMDB0061725
- KEGG Drug
- D09720
- PubChem Compound
- 6451164
- PubChem Substance
- 175427123
- ChemSpider
- 4953643
- BindingDB
- 222178
- 1102270
- ChEBI
- 68606
- ChEMBL
- CHEMBL175691
- ZINC
- ZINC000001554274
- PDBe Ligand
- T27
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Rilpivirine
- PDB Entries
- 2zd1 / 2ze2 / 3bgr / 3qlh / 4g1q / 4icl / 4id5 / 4idk / 4ifv / 4ify … show 19 more
- FDA label
- Download (558 KB)
- MSDS
- Download (568 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Fatty Liver Disease / Human Immunodeficiency Virus (HIV) Infections 1 4 Active Not Recruiting Treatment Human Immunodeficiency Virus (HIV) Infections 1 4 Completed Basic Science Abnormality of Adipose Tissue / Antiviral Drug Adverse Reaction / Body Fat Disorder / Cardiovascular Abnormalities / HIV Lipodystrophy Syndrome / Human Immunodeficiency Virus Type 1 (HIV-1) Infection / Vascular Diseases / Weight Changes 1 4 Completed Prevention HIV Nonoccupational Post-exposure Prophylaxis in Men Who Have Sex With Men 1 4 Completed Treatment Cardiovascular Disease (CVD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, suspension, extended release; kit Intramuscular Kit; suspension, extended release Intramuscular Tablet, film coated Oral Tablet Oral 25 mg Tablet Oral 27.500 mg Tablet, coated Oral 25 mg Tablet, film coated Oral Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 25 mg Tablet Oral Tablet, coated Oral Injection Intramuscular 600 mg Injection Intramuscular 900 mg Injection, suspension Intramuscular 600 MG Injection, suspension Intramuscular 900 MG Suspension Intramuscular 300 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5914331 Yes 1999-06-22 2018-01-02 US US6043230 Yes 2000-03-28 2018-01-25 US US9242986 Yes 2016-01-26 2030-06-08 US US5814639 Yes 1998-09-29 2017-03-29 US US6642245 Yes 2003-11-04 2021-05-04 US US6703396 Yes 2004-03-09 2021-09-09 US US5922695 Yes 1999-07-13 2018-01-25 US US5935946 Yes 1999-08-10 2018-01-25 US US5977089 Yes 1999-11-02 2018-01-25 US US8592397 No 2013-11-26 2024-01-13 US US8716264 No 2014-05-06 2024-01-13 US US7125879 No 2006-10-24 2022-08-09 US US6838464 No 2005-01-04 2021-02-26 US US8080551 No 2011-12-20 2023-04-11 US US8101629 No 2012-01-24 2022-08-09 US US7067522 No 2006-06-27 2019-12-20 US US7638522 No 2009-12-29 2023-04-14 US US8129385 Yes 2012-03-06 2028-04-05 US US8841310 No 2014-09-23 2025-12-09 US US9296769 Yes 2016-03-29 2033-02-15 US US7803788 No 2010-09-28 2022-02-02 US US8754065 Yes 2014-06-17 2033-02-15 US US7390791 Yes 2008-06-24 2025-10-17 US US9457036 No 2016-10-04 2024-01-13 US US9744181 No 2017-08-29 2024-01-13 US US10426780 No 2019-10-01 2031-01-24 US US10857102 No 2020-12-08 2033-01-14 US US8410103 No 2013-04-02 2026-04-28 US US10927129 No 2021-02-23 2026-04-28 US US11224597 No 2011-09-15 2031-09-15 US US11389447 No 2007-06-30 2027-06-30 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 241-243°C Sun, et al.: J. Med. Chem., 41, 4648 (1998) Kashiwada, et al.: Bioorg. Med. Chem. Lett., 11, 183 (2001) water solubility <0.1mg/ml Usach, et al. J Int AIDS Soc. 16(1): 18567. (2013) logP 4.86 Usach, et al. J Int AIDS Soc. 16(1): 18567. (2013) pKa 5.6 Usach, et al. J Int AIDS Soc. 16(1): 18567. (2013) - Predicted Properties
Property Value Source Water Solubility 0.0116 mg/mL ALOGPS logP 3.8 ALOGPS logP 5.47 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 11.43 Chemaxon pKa (Strongest Basic) 4.44 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 97.42 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 111.74 m3·mol-1 Chemaxon Polarizability 40.63 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9929 Blood Brain Barrier + 0.8571 Caco-2 permeable + 0.6609 P-glycoprotein substrate Non-substrate 0.6933 P-glycoprotein inhibitor I Non-inhibitor 0.6604 P-glycoprotein inhibitor II Non-inhibitor 0.7001 Renal organic cation transporter Non-inhibitor 0.8261 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Non-substrate 0.8322 CYP450 3A4 substrate Non-substrate 0.6778 CYP450 1A2 substrate Inhibitor 0.8256 CYP450 2C9 inhibitor Non-inhibitor 0.9105 CYP450 2D6 inhibitor Non-inhibitor 0.9202 CYP450 2C19 inhibitor Non-inhibitor 0.806 CYP450 3A4 inhibitor Non-inhibitor 0.9013 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5439 Ames test Non AMES toxic 0.6229 Carcinogenicity Non-carcinogens 0.9097 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.8139 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9027 hERG inhibition (predictor II) Non-inhibitor 0.841
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-014i-0649000000-96980e5526a79d124034 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0009000000-86d701fd5fe683bc57af Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0009000000-fa7c070ebe5898e76f1d Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0009000000-aeb728d3ab6a115d9917 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0009000000-1aac1ace211699bcbd96 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0219000000-b38116130132fbe72b5d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014s-1940000000-2b13ad7eff3b6ae2c5b8 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 220.0854523 predictedDarkChem Lite v0.1.0 [M-H]- 219.0703523 predictedDarkChem Lite v0.1.0 [M-H]- 185.87868 predictedDeepCCS 1.0 (2019) [M+H]+ 221.2150523 predictedDarkChem Lite v0.1.0 [M+H]+ 221.4128523 predictedDarkChem Lite v0.1.0 [M+H]+ 188.23668 predictedDeepCCS 1.0 (2019) [M+Na]+ 219.4453523 predictedDarkChem Lite v0.1.0 [M+Na]+ 219.6785523 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.64583 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Human immunodeficiency virus 1
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Rna-dna hybrid ribonuclease activity
- Specific Function
- Not Available
- Gene Name
- pol
- Uniprot ID
- Q72547
- Uniprot Name
- Reverse transcriptase/RNaseH
- Molecular Weight
- 65223.615 Da
References
- Garvey L, Winston A: Rilpivirine: a novel non-nucleoside reverse transcriptase inhibitor. Expert Opin Investig Drugs. 2009 Jul;18(7):1035-41. doi: 10.1517/13543780903055056. [Article]
- De Clercq E: Emerging anti-HIV drugs. Expert Opin Emerg Drugs. 2005 May;10(2):241-73. [Article]
- Australian Government: Australian Public Assessment Report for Rilpivirine [Link]
- FDA Approved Drug Products: Edurant (rilpivirine) oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Sharma D, Lau AJ, Sherman MA, Chang TK: Agonism of human pregnane X receptor by rilpivirine and etravirine: comparison with first generation non-nucleoside reverse transcriptase inhibitors. Biochem Pharmacol. 2013 Jun 1;85(11):1700-11. doi: 10.1016/j.bcp.2013.04.002. Epub 2013 Apr 9. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitorInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Weiss J, Haefeli WE: Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7. doi: 10.1016/j.ijantimicag.2013.01.004. Epub 2013 Feb 18. [Article]
- FDA Approved Drug Products: Edurant (rilpivirine) oral tablets [Link]
- Australian Government: Australian Public Assessment Report for Rilpivirine [Link]
- Rilpivirine FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Weiss J, Haefeli WE: Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7. doi: 10.1016/j.ijantimicag.2013.01.004. Epub 2013 Feb 18. [Article]
- Aouri M, Barcelo C, Guidi M, Rotger M, Cavassini M, Hizrel C, Buclin T, Decosterd LA, Csajka C: Population Pharmacokinetics and Pharmacogenetics Analysis of Rilpivirine in HIV-1-Infected Individuals. Antimicrob Agents Chemother. 2016 Dec 27;61(1). pii: AAC.00899-16. doi: 10.1128/AAC.00899-16. Print 2017 Jan. [Article]
- Australian Government: Australian Public Assessment Report for Rilpivirine [Link]
- Actual and Predicted Pharmacokinetic Interactions Between Anticonvulsants and Antiretrovirals [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Weiss J, Haefeli WE: Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7. doi: 10.1016/j.ijantimicag.2013.01.004. Epub 2013 Feb 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Weiss J, Haefeli WE: Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7. doi: 10.1016/j.ijantimicag.2013.01.004. Epub 2013 Feb 18. [Article]
- Australian Government: Australian Public Assessment Report for Rilpivirine [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Australian Government: Australian Public Assessment Report for Rilpivirine [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Australian Government: Australian Public Assessment Report for Rilpivirine [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Australian Government: Australian Public Assessment Report for Rilpivirine [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Weiss J, Haefeli WE: Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7. doi: 10.1016/j.ijantimicag.2013.01.004. Epub 2013 Feb 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Weiss J, Haefeli WE: Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7. doi: 10.1016/j.ijantimicag.2013.01.004. Epub 2013 Feb 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Weiss J, Haefeli WE: Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7. doi: 10.1016/j.ijantimicag.2013.01.004. Epub 2013 Feb 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Weiss J, Haefeli WE: Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7. doi: 10.1016/j.ijantimicag.2013.01.004. Epub 2013 Feb 18. [Article]
Drug created at March 14, 2013 21:23 / Updated at February 20, 2024 23:54