Darunavir

Darunavir
Clinical data


Trade names	Prezista, Prezcobix, others
AHFS/Drugs.com	Monograph
MedlinePlus	a607042
Pregnancy category	AU: B2 US: C (Risk not ruled out)
Routes of administration	by mouth
ATC code	J05AE10 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	37% (without ritonavir), 82% (with ritonavir)
Protein binding	95%
Metabolism	hepatic (CYP3A4)
Biological half-life	15 hours
Excretion	Faeces (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
Synonyms	TMC114
CAS Number	206361-99-1^Y
PubChem CID	213039
DrugBank	DB01264^Y
ChemSpider	184733^Y
UNII	YO603Y8113
KEGG	D03656^Y
ChEBI	CHEBI:367163^Y
ChEMBL	CHEMBL1323^N
NIAID ChemDB	073035
ECHA InfoCard	100.111.730
Chemical and physical data
Formula	C₂₇H₃₇N₃O₇S
Molar mass	547.665 g/mol
3D model (Jmol)	Interactive image
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?)

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, and rash. 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.

Darunavir was approved for medical use in the United States in 2006. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. As of 2015 it is not available as a generic medication. The wholesale cost in the developing world is about 66 USD per month. In the United States it costs more than 200 USD per month.

Darunavir is an OARAC (DHHS) recommended treatment option for adults and adolescents, regardless of whether they have received HIV treatment in the past. In a study of patients that had never received HIV treatment, darunavir was as effective as lopinavir/ritonavir at 96 weeks with a once-daily dosing. It was approved by the FDA on October 21, 2008 for people not previously treated for HIV. As with other antiretrovirals, darunavir does not cure HIV/AIDS.

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