Darunavir

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

Darunavir
Clinical data
Trade namesPrezista, others
Other namesTMC114, DRV, darunavir ethanolate
AHFS/Drugs.comMonograph
MedlinePlusa607042
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
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
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=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)

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

Developed by pharmaceutical company Tibotec, darunavir is named after Arun K. Ghosh, the chemistry professor who discovered the molecule at the University of Illinois at Chicago. It was approved by the Food and Drug Administration (FDA) in June 2006. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.

The fixed-dose combination medication darunavir/cobicistat (Prezcobix, Rezolsta) is available as a single pill.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.