Structure via PubChem · Public domain (PubChem)
darunavir
Sign in to saveAlso 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- Darunavir: A comprehensive profile.Profiles of drug substances, excipients, and related methodology · 2021
- Darunavir.Drugs of today (Barcelona, Spain : 1998) · 2007
- Darunavir/Cobicistat/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection.Drugs · 2018
- Darunavir for use in pregnant women with HIV.Expert review of clinical pharmacology · 2017
- Darunavir for the treatment of HIV infection.Expert opinion on pharmacotherapy · 2018
via PubMed
~7 min read
Encyclopedic overview
9 sectionsContents
- 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.