Darunavir

Darunavir
Clinical data
Pronunciation/dəˈruːnəvɪər/
də-ROO-nə-veer
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
IUPAC name
  • [(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
Chemical and physical data
FormulaC27H37N3O7S
Molar mass547.67 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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 Y
  • Key:CJBJHOAVZSMMDJ-HEXNFIEUSA-N Y
 NY (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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