Ritonavir

For nirmatrelvir combined with ritonavir (sold under the brand name Paxlovid), see Nirmatrelvir/ritonavir.

Ritonavir
Clinical data
Pronunciation/rɪˈtɒnəˌvɪər/
rih-TO-nə-veer
Trade namesNorvir
Other namesRTV
AHFS/Drugs.comMonograph
MedlinePlusa696029
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding98–99%
MetabolismLiver, CYP3A4
Elimination half-life3–4 hours[6][7]
ExcretionMostly fecal
Identifiers
  • 1,3-thiazol-5-ylmethyl N-[(2S,3S,5S)-3-hydroxy-5-[(2S)-3-methyl-2-{[methyl({[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl})carbamoyl]amino}butanamido]-1,6-diphenylhexan-2-yl]carbamate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.125.710 Edit this at Wikidata
Chemical and physical data
FormulaC37H48N6O5S2
Molar mass720.95 g·mol−1
3D model (JSmol)
  • CC(C)c4nc(CN(C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](Cc1ccccc1)C[C@H](O)[C@H](Cc2ccccc2)NC(=O)OCc3cncs3)cs4
  • InChI=1S/C37H48N6O5S2/c1-24(2)33(42-36(46)43(5)20-29-22-49-35(40-29)25(3)4)34(45)39-28(16-26-12-8-6-9-13-26)18-32(44)31(17-27-14-10-7-11-15-27)41-37(47)48-21-30-19-38-23-50-30/h6-15,19,22-25,28,31-33,44H,16-18,20-21H2,1-5H3,(H,39,45)(H,41,47)(H,42,46)/t28-,31-,32-,33-/m0/s1 checkY
  • Key:NCDNCNXCDXHOMX-XGKFQTDJSA-N checkY

Ritonavir, sold under the brand name Norvir, is an antiretroviral medication used along with other medications to treat HIV/AIDS.[4][5][8] This combination treatment is known as highly active antiretroviral therapy (HAART).[8] Ritonavir is a protease inhibitor, though it now mainly serves to boost the potency of other protease inhibitors.[8][9] It may also be used in combination with other medications to treat hepatitis C and COVID-19.[10][11] It is taken by mouth.[8]

Common side effects of ritonavir include nausea, vomiting, loss of appetite, diarrhea, and numbness of the hands and feet.[8] Serious side effects include liver complications, pancreatitis, allergic reactions, and arrhythmias.[8] Serious interactions may occur with a number of other medications including amiodarone and simvastatin.[8] At low doses, it is considered to be acceptable for use during pregnancy.[12] Ritonavir is of the protease inhibitor class.[8] However, it is also commonly used to inhibit the enzyme that metabolizes other protease inhibitors.[13] This inhibition allows lower doses of these latter medications to be used.[13]

Ritonavir was patented in 1989 and came into medical use in 1996.[14][15] It is on the World Health Organization's List of Essential Medicines.[16][17] Ritonavir capsules were approved as a generic medication in the United States in 2020.[18]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved October 22, 2023.
  2. ^ "Notice: Nirmatrelvir (COVID-19) added to Prescription Drug List (PDL)". Health Canada. January 17, 2022. Archived from the original on May 29, 2022. Retrieved June 25, 2022.
  3. ^ "Norvir Product information". Health Canada. April 25, 2012. Retrieved June 25, 2022.
  4. ^ a b "Norvir- ritonavir tablet, film coated Norvir- ritonavir solution Norvir- ritonavir powder". DailyMed. Archived from the original on November 18, 2021. Retrieved November 17, 2021.
  5. ^ a b Cite error: The named reference Norvir EPAR was invoked but never defined (see the help page).
  6. ^ Hsu A, Granneman GR, Witt G, Locke C, Denissen J, Molla A, et al. (May 1997). "Multiple-dose pharmacokinetics of ritonavir in human immunodeficiency virus-infected subjects". Antimicrobial Agents and Chemotherapy. 41 (5): 898–905. doi:10.1128/aac.41.5.898. PMC 163822. PMID 9145841.
  7. ^ Danner SA, Carr A, Leonard JM, Lehman LM, Gudiol F, Gonzales J, Raventos A, Rubio R, Bouza E, Pintado V, Aguado AG, Garcia de Lomas J, Delgado R, Borleffs JC, Hsu A, Valdes JM, Boucher CA, Cooper DA (December 1995). "A short-term study of the safety, pharmacokinetics, and efficacy of ritonavir, an inhibitor of HIV-1 protease. European-Australian Collaborative Ritonavir Study Group". The New England Journal of Medicine. 333 (23): 1528–1533. doi:10.1056/NEJM199512073332303. hdl:2445/121979. PMID 7477167.
  8. ^ a b c d e f g h "Ritonavir". The American Society of Health-System Pharmacists. Archived from the original on October 17, 2015. Retrieved October 23, 2015.
  9. ^ Talha B, Dhamoon AS (August 8, 2023). "Ritonavir". StatPearls. StatPearls Publishing. PMID 31335032. Retrieved January 6, 2024.
  10. ^ Cite error: The named reference FDA-ucm427530 was invoked but never defined (see the help page).
  11. ^ Akinosoglou K, Schinas G, Gogos C (November 2022). "Oral Antiviral Treatment for COVID-19: A Comprehensive Review on Nirmatrelvir/Ritonavir". Viruses. 14 (11): 2540. doi:10.3390/v14112540. PMC 9696049. PMID 36423149.
  12. ^ "Ritonavir Pregnancy and Breastfeeding Warnings". drugs.com. Archived from the original on September 7, 2015. Retrieved October 23, 2015.
  13. ^ a b British National Formulary 69 (69 ed.). Pharmaceutical Pr. March 31, 2015. p. 426. ISBN 9780857111562.
  14. ^ Hacker M (2009). Pharmacology principles and practice. Amsterdam: Academic Press/Elsevier. p. 550. ISBN 9780080919225. Archived from the original on June 17, 2020. Retrieved September 10, 2017.
  15. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 509. ISBN 9783527607495. Archived from the original on June 20, 2021. Retrieved August 27, 2020.
  16. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  17. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  18. ^ "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). Archived from the original on January 26, 2021. Retrieved February 13, 2021.