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Darunavir

Darunavir
Clinical data
Trade namesPrezista, others[1]
Other namesTMC114, DRV, darunavir ethanolate
AHFS/Drugs.comMonograph
MedlinePlusa607042
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classHIV protease inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability37% (without ritonavir), 82% (with ritonavir)
Protein binding95%
MetabolismLiver (CYP3A4)
Elimination half-life15 hours (with ritonavir)
ExcretionFeces (80%), urine (14%)
Identifiers
  • [(1R,5S,6R)-2,8-dioxabicyclo[3.3.0]oct-6-yl] N-[(2S,3R)-4- [(4-aminophenyl)sulfonyl- (2-methylpropyl)amino]-3-hydroxy-1-phenyl- butan-2-yl] carbamate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.111.730 Edit this at Wikidata
Chemical and physical data
FormulaC27H37N3O7S
Molar mass547.67 g·mol−1
3D model (JSmol)
  • O=S(=O)(c1ccc(N)cc1)N(CC(C)C)C[C@@H](O)[C@@H](NC(=O)O[C@H]2CO[C@H]3OCC[C@@H]23)Cc4ccccc4
  • InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1 checkY
  • Key:CJBJHOAVZSMMDJ-HEXNFIEUSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Darunavir (DRV), sold under the brand name Prezista among others, is an antiretroviral medication used to treat and prevent HIV/AIDS.[1] It is generally recommended for use with other antiretrovirals.[1][4] It is often used with low doses of ritonavir or cobicistat to increase darunavir levels.[1] It may be used for prevention after a needlestick injury or other potential exposure.[1] It is taken by mouth once to twice a day.[1]

Common side effects include diarrhea, nausea, abdominal pain, headache, rash and vomiting.[1][4] Severe side effects include allergic reactions, liver problems, and skin rashes such as toxic epidermal necrolysis.[1] While poorly studied in pregnancy it appears to be safe for the baby.[2] It is of the protease inhibitor (PI) class and works by blocking HIV protease.[1]

Darunavir was approved by the US Food and Drug Administration (FDA) in June 2006.[6][7] It is on the World Health Organization's List of Essential Medicines.[8] It is available as a generic medication.[9]

It is available in the fixed-dose combination medication darunavir/cobicistat (Prezcobix, Rezolsta),[10][11] and in the fixed-dose combination medication darunavir/cobicistat/emtricitabine/tenofovir alafenamide (Symtuza).[12][13]

  1. ^ a b c d e f g h i "Darunavir". The American Society of Health-System Pharmacists. Archived from the original on 10 November 2016. Retrieved 28 November 2016.
  2. ^ a b "Darunavir (Prezista) Use During Pregnancy". Drugs.com. 23 October 2018. Archived from the original on 20 December 2016. Retrieved 21 April 2020.
  3. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.
  4. ^ a b c "Prezista- darunavir tablet, film coated Prezista- darunavir suspension". DailyMed. 6 June 2019. Archived from the original on 6 February 2019. Retrieved 21 April 2020.
  5. ^ Cite error: The named reference Prezista EPAR was invoked but never defined (see the help page).
  6. ^ "Drug Approval Package: Prezista (Darumavir) NDA #021976". U.S. Food and Drug Administration (FDA). Archived from the original on 1 July 2016. Retrieved 26 May 2024.
  7. ^ MacArthur RD (April 2007). "Darunavir: promising initial results". Lancet. 369 (9568): 1143–1144. doi:10.1016/S0140-6736(07)60499-1. PMID 17416241. S2CID 31175809.
  8. ^ 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.
  9. ^ "2022 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
  10. ^ "Prezcobix - darunavir ethanolate and cobicistat tablet, film coated". DailyMed. 2 January 2024. Archived from the original on 28 November 2023. Retrieved 26 May 2024.
  11. ^ "Darunavir / Cobicistat". Clinicalinfo. 27 November 2023. Archived from the original on 25 February 2024. Retrieved 26 May 2024.
  12. ^ "Symtuza - darunavir, cobicistat, emtricitabine, and tenofovir alafenamide tablet, film coated". DailyMed. 18 August 2023. Archived from the original on 9 July 2021. Retrieved 26 May 2024.
  13. ^ "Darunavir / Cobicistat / Emtricitabine / Tenofovir Alafenamide". Clinicalinfo. 20 June 2023. Archived from the original on 23 January 2024. Retrieved 26 May 2024.
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