DARUNAVIR DIHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H37N3O7S.2H2O
Molecular Weight	583.694
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.[H][C@]12OCC[C@@]1([H])[C@H](CO2)OC(=O)N[C@@H](CC3=CC=CC=C3)[C@H](O)CN(CC(C)C)S(=O)(=O)C4=CC=C(N)C=C4

InChI

InChIKey=QBRFTVBGMDIHGZ-OCMLJPQKSA-N

InChI=1S/C27H37N3O7S.2H2O/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);2*1H2/t22-,23-,24+,25-,26+;;/m0../s1

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23708741 | http://adisinsight.springer.com/drugs/800016726

Darunavir (trade name Prezista) is an orally active bis-furan-sulfonamide inhibitor of human immunodeficiency virus (HIV-1) protease. Darunavir was developed by Tibotec Pharmaceuticals (now Janssen R&D Ireland). Darunavir is indicated for the treatment of HIV-1 infection in adult and pediatric patients 3 years of age and older. The drug is co-administered with low-dose ritonavir and other anti-HIV agents. It is the only antiretroviral that has been registered at two different doses, 800/100 mg once-daily or 600/100 mg twice-daily, allowing its administration throughout the entire course of HIV disease, from naive subjects without any HIV-1 resistance to heavily treatment-experienced subjects with widespread triple-class family resistance.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 protease 35 Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15479840	Inhibitor 8297		4.5 pM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 151 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf	Primary		Approved 8429	PREZISTA Approved Use PREZISTA is a human immunodeficiency virus (HIV-1) protease inhibitor indicated for the treatment of HIV-1 infection in adult patients. PREZISTA is also indicated for the treatment of HIV-1 infection in pediatric patients 3 years of age and older. PREZISTA must be co-administered with ritonavir (PREZISTA/ritonavir) and with other antiretroviral agents. Launch Date 2006

C_max

Value	Dose	Co-administered	Analyte	Population
5272 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21926632/	800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir	Ritonavir	DARUNAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
93026 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf	800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir	Ritonavir	DARUNAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
124698 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir	Ritonavir	DARUNAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
57055 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21926632/	800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir	Ritonavir	DARUNAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
126377 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir	Ritonavir	DARUNAVIR plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
15 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf	800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir	Ritonavir	DARUNAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
15 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir	Ritonavir	DARUNAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf	800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir	Ritonavir	DARUNAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf	600 mg 2 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Ritonavir	Ritonavir	DARUNAVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://pubmed.ncbi.nlm.nih.gov/20010070 Page: p.227	unhealthy, 43 n = 127 Health Status: unhealthy Condition: HIV-1 infection Age Group: 43 Sex: M+F Population Size: 127 Sources: https://pubmed.ncbi.nlm.nih.gov/20010070 Page: p.227	Disc. AE: Headache, Gastrointestinal disorder NOS... AEs leading to discontinuation/dose reduction: Headache (grade 3, 0.79%) Gastrointestinal disorder NOS (5.51%) Sources: https://pubmed.ncbi.nlm.nih.gov/20010070 Page: p.227
3200 mg single, oral Overdose Dose: 3200 mg Route: oral Route: single Dose: 3200 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.22	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.22	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.22
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	Disc. AE: Drug-induced hepatitis, Hepatitis acute... AEs leading to discontinuation/dose reduction: Drug-induced hepatitis Hepatitis acute Cytolytic hepatitis Reaction skin (grade 1-3) Stevens-Johnson syndrome Toxic epidermal necrolysis Diabetes mellitus Hyperglycemia Fat redistribution Fat tissue increased Immune reconstitution syndrome Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.8	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.8	Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (grade 1-2, 0.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.8

AEs

AE	Significance	Dose	Population
Gastrointestinal disorder NOS	5.51% Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://pubmed.ncbi.nlm.nih.gov/20010070 Page: p.227	unhealthy, 43 n = 127 Health Status: unhealthy Condition: HIV-1 infection Age Group: 43 Sex: M+F Population Size: 127 Sources: https://pubmed.ncbi.nlm.nih.gov/20010070 Page: p.227
Headache	grade 3, 0.79% Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://pubmed.ncbi.nlm.nih.gov/20010070 Page: p.227	unhealthy, 43 n = 127 Health Status: unhealthy Condition: HIV-1 infection Age Group: 43 Sex: M+F Population Size: 127 Sources: https://pubmed.ncbi.nlm.nih.gov/20010070 Page: p.227
Cytolytic hepatitis	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Diabetes mellitus	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Drug-induced hepatitis	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Fat redistribution	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Fat tissue increased	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Hepatitis acute	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Hyperglycemia	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Immune reconstitution syndrome	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Stevens-Johnson syndrome	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Toxic epidermal necrolysis	Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Reaction skin	grade 1-3 Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.1
Rash	grade 1-2, 0.5% Disc. AE	800 mg 1 times / day multiple, oral Recommended Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Co-administed with:: ritonavir, oral(100 mg; qd) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.8	unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021976s021lbl.pdf Page: p.8

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:367163	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:367163
ChemicalBook	CB51176244	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB51176244
MolPort	MolPort-003-846-141	https://www.molport.com/shop/molecule-link/MolPort-003-846-141
ZINC	ZINC000003955219	http://zinc15.docking.org/substances/ZINC000003955219
eMolecules	35833368	https://www.emolecules.com/cgi-bin/more?vid=35833368
eMolecules	36557635	https://www.emolecules.com/cgi-bin/more?vid=36557635

PubMed

Title	Date	PubMed
New HIV treatment.	2006 Sep-Oct	17326304
Clinical pharmacokinetics of darunavir.	2007	17713972
Pharmacokinetics of darunavir/ritonavir and TMC125 alone and coadministered in HIV-negative volunteers.	2007	17713162
Pharmacokinetic interaction between TMC114/r and efavirenz in healthy volunteers.	2007	17668559
Fast and simultaneous determination of darunavir and eleven other antiretroviral drugs for therapeutic drug monitoring: method development and validation for the determination of all currently approved HIV protease inhibitors and non-nucleoside reverse transcriptase inhibitors in human plasma by liquid chromatography coupled with electrospray ionization tandem mass spectrometry.	2007	17610214
Pharmacokinetics of darunavir (TMC114) and atazanavir during coadministration in HIV-negative, healthy volunteers.	2007	17596110
Antiretroviral treatment of HIV infection: Swedish recommendations 2007.	2007	17577810
Anti-HIV drugs.	2007	17550060
AIDS in the Third World: how to stop the HIV infection?	2007	17550059
Key reports from the XV International HIV Drug Resistance Workshop 2006.	2007	17503758
When and how to use tipranavir and darunavir.	2007 Apr	17479503
The effect of different meal types on the pharmacokinetics of darunavir (TMC114)/ritonavir in HIV-negative healthy volunteers.	2007 Apr	17389557
Efficacy and safety of darunavir-ritonavir at week 48 in treatment-experienced patients with HIV-1 infection in POWER 1 and 2: a pooled subgroup analysis of data from two randomised trials.	2007 Apr 7	17416261
Darunavir: promising initial results.	2007 Apr 7	17416241
Darunavir (TMC114): a new HIV-1 protease inhibitor.	2007 Aug	17696796
Development of therapeutics for AIDS: structure-based molecular targeting.	2007 Aug	17625972
Darunavir: a second-generation protease inhibitor.	2007 Aug 1	17646561
Overview of boosted protease inhibitors in treatment-experienced HIV-infected patients.	2007 Dec	17890281
Darunavir, a conceptually new HIV-1 protease inhibitor for the treatment of drug-resistant HIV.	2007 Dec 15	17900913
Darunavir (TMC114) approved by the FDA.	2007 Feb	17763549
Efficacy and safety of TMC114/ritonavir in treatment-experienced HIV patients: 24-week results of POWER 1.	2007 Feb 19	17301557
48-week study results show DRV's staying power.	2007 Jan	17523243
Anti-HIV agents. Darunavir and some antidepressants.	2007 Jan	17390480
Pharmacokinetics and antiretroviral response to darunavir/ritonavir and etravirine combination in patients with high-level viral resistance.	2007 Jul 11	17589191
Efficacy and safety of darunavir-ritonavir compared with that of lopinavir-ritonavir at 48 weeks in treatment-experienced, HIV-infected patients in TITAN: a randomised controlled phase III trial.	2007 Jul 7	17617272
Efficacy and safety of TMC125 (etravirine) in treatment-experienced HIV-1-infected patients in DUET-1: 24-week results from a randomised, double-blind, placebo-controlled trial.	2007 Jul 7	17617270
No patient left behind--better treatments for resistant HIV infection.	2007 Jul 7	17617250
Safety, tolerability, and efficacy of darunavir (TMC114) with low-dose ritonavir in treatment-experienced, hepatitis B or C co-infected patients in POWER 1 and 3.	2007 Jul-Aug	17720661
A novel bis-tetrahydrofuranylurethane-containing nonpeptidic protease inhibitor (PI), GRL-98065, is potent against multiple-PI-resistant human immunodeficiency virus in vitro.	2007 Jun	17371811
Prezista gets EU approval.	2007 Mar	17428190
Editorial comment: impact of darunavir for salvage therapy.	2007 Mar	17396333
Darunavir: an overview of an HIV protease inhibitor developed to overcome drug resistance.	2007 Mar	17396332
Consensus recommendation from a group of German experts for the use of enfuvirtide in heavily pretreated HIV patients.	2007 Mar 26	17507306
Tibotec and Aspen collaborate on Prezista.	2007 May	17546795
HIV-1 subtype B protease and reverse transcriptase amino acid covariation.	2007 May	17500586
Relative antiviral efficacy of ritonavir-boosted darunavir and ritonavir-boosted tipranavir vs. control protease inhibitor in the POWER and RESIST trials.	2007 May	17461854
Prediction of clinical benefits of ritonavir-boosted TMC114 from treatment effects on CD4 counts and HIV RNA.	2007 May	17461851
Key amprenavir resistance mutations counteract dramatic efficacy of darunavir in highly experienced patients.	2007 May 31	17502734
Analysis of treatment costs for HIV RNA reductions and CD4 increases for darunavir versus other antiretrovirals in treatment-experienced, HIV-infected patients.	2007 May-Jun	17621459
Prevalence of darunavir resistance mutations in HIV-1-infected patients failing other protease inhibitors.	2007 Oct	17646201
Quantification of darunavir (TMC114) in human plasma by high-performance liquid chromatography with ultra-violet detection.	2007 Oct 1	17706473
Predicting HIV care costs using CD4 counts from clinical trials.	2007 Sep	17803366
Lessons Learned From 2 Patients With Multidrug-Resistant HIV-1 Infection Successfully Treated With a Darunavir-Containing Antiretroviral Treatment Regimen.	2007 Sep	17641132
Safety and efficacy of darunavir (TMC114) with low-dose ritonavir in treatment-experienced patients: 24-week results of POWER 3.	2007 Sep 1	17621237
Tipranavir: a new option for the treatment of drug-resistant HIV infection.	2007 Sep 15	17712762
Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization.	2007 Sep 28	17635930
Potent new antiviral compound shows similar inhibition and structural interactions with drug resistant mutants and wild type HIV-1 protease.	2007 Sep 6	17696515
Darunavir offers potent new combo when used with enfuvirtide in ritonavir-boosted regimen.	2007 Winter	17405221
Design of HIV protease inhibitors targeting protein backbone: an effective strategy for combating drug resistance.	2008 Jan	17722874
Quality control of protease inhibitors.	2008 Jun	17828738

Patents

Sample Use Guides

In Vivo Use Guide

Treatment-naïve adult patients and treatment-experienced adult patients with no darunavir resistance associated substitutions: 800 mg (two 400 mg tablets) taken with ritonavir 100 mg once daily and with food. Treatment-experienced adult patients with at least one darunavir resistance associated substitution: 600 mg (one 600 mg tablet) taken with ritonavir 100 mg twice daily and with food. Pediatric patients (3 to less than 18 years of age and weighing at least 10 kg): dosage of PREZISTA and ritonavir is based on body weight and should not exceed the treatmentexperienced adult dose. Do not use once daily dosing in pediatric patients. PREZISTA should be taken with ritonavir twice daily and with food.

Route of Administration: Oral

In Vitro Use Guide

Darunavir exhibits activity against laboratory strains and clinical isolates of HIV-1 and laboratory strains of HIV-2 in acutely infected T-cell lines, human peripheral blood mononuclear cells and human monocytes/macrophages with median EC50 values ranging from 1.2 to 8.5 nM (0.7 to 5.0 ng/mL). Darunavir demonstrates antiviral activity in cell culture against a broad panel of HIV-1 group M (A, B, C, D, E, F, G), and group O primary isolates with EC50 values ranging from less than 0.1 to 4.3 nM.

Name

Type

Language

DARUNAVIR DIHYDRATE

Common Name

English

DARUNAVIR HYDRATE

Preferred Name

English

CARBAMIC ACID, N-((1S,2R)-3-(((4-AMINOPHENYL)SULFONYL)(2-METHYLPROPYL)AMINO)-2-HYDROXY-1-(PHENYLMETHYL)PROPYL)-, (3R,3AS,6AR)-HEXAHYDROFURO(2,3-B)FURAN-3-YL ESTER, HYDRATE (1:2)

Systematic Name

English

TMC-114 HYDRATE

Common Name

English

TMC114 HYDRATE

Common Name

English

Code System Code Type Description

CAS

2281870-65-1