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darunavir

Structure via PubChem · Public domain (PubChem)

EntityQ3765251· pop 25· linked from 196 articles

Also known as MC-114, TMC114, (3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamate, (3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate, (3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamate, [(S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester, N-((1S,2R)-3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-benzylpropyl)((1S,2R,5R)-4,6-dioxabicyclo(3.3.0)oct-2-yloxy)carboxamide, {(1S,2R)-3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester

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.

Key facts

Drug.Verifiedfields
changed
Drug.verifiedrevid
460773860
Drug.image
File:Darunavir structure.svg
Drug.image_class
skin-invert-image
Drug.width
200
Drug.image2
Darunavir-from-xtal-3D-bs-17.png
Drug.image_class2
bg-transparent
Drug.tradename
Prezista, others
Drug.MedlinePlus
a607042
Drug.DailyMedID
Darunavir
Drug.pregnancy_AU
B2
Drug.routes_of_administration
By mouth
Drug.class
HIV protease inhibitor
Drug.ATC_prefix
J05
Drug.ATC_suffix
AE10
Drug.legal_AU
S4
Drug.legal_CA
Rx-only
Drug.legal_UK
POM

via Wikipedia infobox

Chemical data

Formula
C27H37N3O7S
Molecular weight
547.7 g/mol
IUPAC name
[(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
SMILES
CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CO[C@@H]3[C@H]2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)N
InChIKey
CJBJHOAVZSMMDJ-HEXNFIEUSA-N
XLogP
2.9
Polar surface area
149 Ų
H-bond donors
3
H-bond acceptors
9
Formal charge
0

via PubChem

Research

2,190 papers

via PubMed

~7 min read

Encyclopedic overview

9 sections
Contents
  • Medical uses
  • Adverse effects
  • Drug interactions
  • Mechanism of action
  • Catalytic site
  • History
  • Society and culture
  • Economics
  • References

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.

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.

Excerpted from Wikipedia’s “darunavir” article, available under the CC BY-SA 4.0 licence.

Gallery (3)