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Identification
NameDarunavir
Accession NumberDB01264  (EXPT00002)
TypeSmall Molecule
GroupsApproved
Description

Darunavir is a protease inhibitor used to treat HIV. It acts on the HIV aspartyl protease which the virus needs to cleave the HIV polyprotein into its functional fragments.

Structure
Thumb
Synonyms
(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)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamate
(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)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate
[(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
{(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
Darunavirum
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
TMC-114
TMC114
External Identifiers
  • AIDS073035
  • TMC114
  • UIC-94017
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pat-darunavirtablet150 mgoralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-darunavirtablet800 mgoralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-darunavirtablet600 mgoralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-darunavirtablet400 mgoralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-darunavirtablet75 mgoralPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Prezistatablet, film coated400 mg/1oralREMEDYREPACK INC.2013-05-09Not applicableUs
Prezistatablet300 mgoralJanssen Inc2006-08-092011-07-27Canada
Prezistatablet, film coated150 mg/1oralJanssen Products LP2009-04-27Not applicableUs
Prezistatablet800 mgoralJanssen Inc2012-11-09Not applicableCanada
Prezistatablet, film coated75 mg/1oralJanssen Products LP2009-01-14Not applicableUs
Prezistatablet150 mgoralJanssen Inc2012-04-16Not applicableCanada
Prezistatablet, film coated600 mg/1oralJanssen Products LP2008-03-08Not applicableUs
Prezistasuspension100 mgoralJanssen Inc2014-08-06Not applicableCanada
Prezistatablet75 mgoralJanssen Inc2009-12-16Not applicableCanada
Prezistatablet, film coated600 mg/1oralPhysicians Total Care, Inc.2012-10-16Not applicableUs
Prezistatablet600 mgoralJanssen Inc2009-03-17Not applicableCanada
Prezistatablet, film coated400 mg/1oralPhysicians Total Care, Inc.2008-12-09Not applicableUs
Prezistatablet400 mgoralJanssen Inc2009-04-01Not applicableCanada
Prezistatablet, film coated600 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Prezistatablet, film coated800 mg/1oralJanssen Products LP2012-11-09Not applicableUs
Prezistatablet, film coated400 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Prezistasuspension100 mg/mLoralJanssen Products LP2011-12-16Not applicableUs
Prezistatablet, film coated800 mg/1oralREMEDYREPACK INC.2013-05-29Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
PrezcobixJanssen Inc
Salts
Name/CASStructureProperties
Darunavir ethanolate
ThumbNot applicableDBSALT001338
Categories
UNIIYO603Y8113
CAS number206361-99-1
WeightAverage: 547.664
Monoisotopic: 547.235221243
Chemical FormulaC27H37N3O7S
InChI KeyInChIKey=CJBJHOAVZSMMDJ-HEXNFIEUSA-N
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
IUPAC Name
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
SMILES
[H][C@@]12CCO[C@]1([H])OC[C@@H]2OC(=O)N[C@@H](CC1=CC=CC=C1)[[email protected]](O)CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Phenylbutylamine
  • Aminobenzenesulfonamide
  • Sulfonylaniline
  • Amphetamine or derivatives
  • Substituted aniline
  • Furofuran
  • Aniline
  • Primary aromatic amine
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Oxolane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationDarunavir, co-administered with ritonavir, and with other antiretroviral agents, is indicated for the treatment of human immunodeficiency virus (HIV) infection in antiretroviral treatment-experienced adult patients, such as those with HIV-1 strains resistant to more than one protease inhibitor.
PharmacodynamicsDarunavir is an inhibitor of the human immunodeficiency virus (HIV) protease. In studies, the drug, co-administered with ritonavir in combination therapy, significantly reduced viral load and increased CD4 cell counts in this treatment-experienced patient population (Tibotec, 2006, Product Monograph, Prezista 2006). Darunavir is used as an adjunct therapy with low dose ritonavir, which inhibits cytochrome P450 3A (CYP3A) which increases the bioavailability and half life of darunavir.
Mechanism of actionDarunavir is a HIV protease inhibitor which prevents HIV replication by binding to the enzyme's active site, thereby preventing the dimerization and the catalytic activity of the HIV-1 protease. Darunavir selectively inhibits the cleavage of HIV encoded Gag-Pol polyproteins in virus-infected cells, which prevents the formation of mature infectious virus particles. Structual analyses suggests that the close contact that darunavir has with the main chains of the protease active site amino acids (Asp-29 and Asp-30) is an important contributing factor to its potency and wide spectrum of activity against multi-protease inhibitor resistant HIV-1 variants. Darunavir can also adapt to the changing shape of a protease enzyme because of its molecular flexibility. Darunavir is known to bind to two distinct sites on the enzyme: the active site cavity and the surface of one of the flexible flaps in the protease dimer.
Related Articles
AbsorptionThe absolute oral bioavailability of a single 600 mg dose of darunavir alone and after co-administration with 100 mg ritonavir twice daily was 37% and 82%, respectively.
Volume of distributionNot Available
Protein bindingDarunavir is approximately 95% bound to plasma proteins. Darunavir binds primarily to plasma alpha 1-acid glycoprotein (AAG).
Metabolism

Hepatic. Darunavir is extensively metabolized by CYP enzymes, primarily by CYP3A.

Route of eliminationDarunavir is primarily metabolized by CYP3A. Darunavir is extensively metabolized by CYP enzymes, primarily by CYP3A. A mass balance study in healthy volunteers showed that after single dose administration of 400 mg 14C-darunavir, co-administered with 100 mg ritonavir, approximately 79.5% and 13.9% of the administered dose of 14C-darunavir was recovered in the feces and urine, respectively.
Half lifeThe terminal elimination half-life of darunavir was approximately 15 hours when combined with ritonavir.
Clearance
  • 32.8 L/hr [Healthy volunteers receiving intravenous administration of 400 mg of darunavir]
  • 5.9 L/hr [Healthy volunteers receiving intravenous administrations of 400 mg of darunavir and 100 mg of ritonavir twice daily]
ToxicityNot Available
Affected organisms
  • Human Immunodeficiency Virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9636
Blood Brain Barrier-0.5518
Caco-2 permeable+0.7274
P-glycoprotein substrateSubstrate0.7464
P-glycoprotein inhibitor IInhibitor0.7588
P-glycoprotein inhibitor IINon-inhibitor0.8683
Renal organic cation transporterNon-inhibitor0.8847
CYP450 2C9 substrateNon-substrate0.5747
CYP450 2D6 substrateSubstrate0.6809
CYP450 3A4 substrateSubstrate0.6496
CYP450 1A2 substrateNon-inhibitor0.7328
CYP450 2C9 inhibitorNon-inhibitor0.6999
CYP450 2D6 inhibitorNon-inhibitor0.8784
CYP450 2C19 inhibitorNon-inhibitor0.6587
CYP450 3A4 inhibitorNon-inhibitor0.5076
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7132
Ames testNon AMES toxic0.5933
CarcinogenicityNon-carcinogens0.7991
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5482 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9824
hERG inhibition (predictor II)Non-inhibitor0.857
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral
Tablet, film coatedoral
Suspensionoral100 mg
Suspensionoral100 mg/mL
Tabletoral150 mg
Tabletoral300 mg
Tabletoral400 mg
Tabletoral600 mg
Tabletoral75 mg
Tabletoral800 mg
Tablet, film coatedoral150 mg/1
Tablet, film coatedoral400 mg/1
Tablet, film coatedoral600 mg/1
Tablet, film coatedoral75 mg/1
Tablet, film coatedoral800 mg/1
Prices
Unit descriptionCostUnit
Prezista 600 mg tablet25.75USD tablet
Prezista 400 mg tablet18.74USD tablet
Prezista 300 mg tablet16.2USD tablet
Prezista 150 mg tablet4.59USD tablet
Prezista 75 mg tablet2.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2224738 No2002-08-272016-06-28Canada
CA2469343 No2008-05-132022-12-12Canada
US5843946 Yes1996-06-012016-06-01Us
US6037157 Yes1996-12-262016-12-26Us
US6335460 No1992-08-252012-08-25Us
US6703403 Yes1996-12-262016-12-26Us
US7470506 Yes1999-12-232019-12-23Us
US7700645 Yes2007-06-262027-06-26Us
US8148374 No2009-09-032029-09-03Us
US8518987 Yes2004-08-162024-08-16Us
US8597876 Yes1999-12-232019-12-23Us
USRE42889 Yes1997-04-192017-04-19Us
USRE43596 Yes1997-11-092017-11-09Us
USRE43802 Yes1997-04-192017-04-19Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityApproximately 0.15 mg/mL at 20 °C as ethanolate saltNot Available
logP1.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0668 mg/mLALOGPS
logP1.76ALOGPS
logP2.82ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.59ChemAxon
pKa (Strongest Basic)2.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area140.42 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity142.34 m3·mol-1ChemAxon
Polarizability57.24 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US05158713
General References
  1. Back D, Sekar V, Hoetelmans RM: Darunavir: pharmacokinetics and drug interactions. Antivir Ther. 2008;13(1):1-13. [PubMed:18389894 ]
  2. Tremblay CL: Combating HIV resistance - focus on darunavir. Ther Clin Risk Manag. 2008 Aug;4(4):759-66. [PubMed:19209258 ]
  3. Koh Y, Matsumi S, Das D, Amano M, Davis DA, Li J, Leschenko S, Baldridge A, Shioda T, Yarchoan R, Ghosh AK, Mitsuya H: Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization. J Biol Chem. 2007 Sep 28;282(39):28709-20. Epub 2007 Jul 17. [PubMed:17635930 ]
  4. Kovalevsky AY, Tie Y, Liu F, Boross PI, Wang YF, Leshchenko S, Ghosh AK, Harrison RW, Weber IT: Effectiveness of nonpeptide clinical inhibitor TMC-114 on HIV-1 protease with highly drug resistant mutations D30N, I50V, and L90M. J Med Chem. 2006 Feb 23;49(4):1379-87. [PubMed:16480273 ]
  5. De Meyer S, Azijn H, Surleraux D, Jochmans D, Tahri A, Pauwels R, Wigerinck P, de Bethune MP: TMC114, a novel human immunodeficiency virus type 1 protease inhibitor active against protease inhibitor-resistant viruses, including a broad range of clinical isolates. Antimicrob Agents Chemother. 2005 Jun;49(6):2314-21. [PubMed:15917527 ]
  6. Link [Link]
External Links
ATC CodesJ05AE10J05AR14
AHFS Codes
  • 08:18.08.08
PDB EntriesNot Available
FDA labelDownload (281 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Darunavir.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Darunavir.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Darunavir.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Darunavir.
AlmotriptanThe serum concentration of Almotriptan can be increased when it is combined with Darunavir.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Darunavir.
AlosetronThe serum concentration of Alosetron can be increased when it is combined with Darunavir.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Darunavir.
AmiodaroneThe serum concentration of Amiodarone can be increased when it is combined with Darunavir.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Darunavir.
AmoxapineThe serum concentration of Amoxapine can be increased when it is combined with Darunavir.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Darunavir.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Darunavir.
AstemizoleThe serum concentration of Astemizole can be increased when it is combined with Darunavir.
AtomoxetineThe serum concentration of Atomoxetine can be increased when it is combined with Darunavir.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Darunavir.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Darunavir.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Darunavir.
BarnidipineThe serum concentration of Barnidipine can be increased when it is combined with Darunavir.
BatimastatThe serum concentration of Darunavir can be increased when it is combined with Batimastat.
BedaquilineThe serum concentration of Bedaquiline can be increased when it is combined with Darunavir.
BepridilThe metabolism of Bepridil can be decreased when combined with Darunavir.
BexaroteneThe serum concentration of Darunavir can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Darunavir can be decreased when it is combined with Boceprevir.
BortezomibThe serum concentration of Bortezomib can be increased when it is combined with Darunavir.
BosentanThe serum concentration of Darunavir can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Darunavir.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Darunavir.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Darunavir.
BrinzolamideThe serum concentration of Brinzolamide can be increased when it is combined with Darunavir.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Darunavir.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Darunavir.
CabozantinibThe serum concentration of Cabozantinib can be increased when it is combined with Darunavir.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Darunavir.
CaptoprilThe serum concentration of Captopril can be increased when it is combined with Darunavir.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Darunavir.
CarvedilolThe serum concentration of Carvedilol can be increased when it is combined with Darunavir.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Darunavir.
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Darunavir.
ChlorphenamineThe serum concentration of Chlorphenamine can be increased when it is combined with Darunavir.
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Darunavir.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Darunavir.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Darunavir.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Darunavir.
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Darunavir.
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Darunavir.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Darunavir.
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Darunavir.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Darunavir.
CyclophosphamideThe risk or severity of adverse effects can be increased when Darunavir is combined with Cyclophosphamide.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Darunavir.
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Darunavir.
DabrafenibThe serum concentration of Darunavir can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be increased when it is combined with Darunavir.
DapoxetineThe serum concentration of Dapoxetine can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Darunavir.
DeferasiroxThe serum concentration of Darunavir can be decreased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Darunavir.
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Darunavir.
DextromethorphanThe serum concentration of Dextromethorphan can be increased when it is combined with Darunavir.
DidanosineThe serum concentration of Didanosine can be decreased when it is combined with Darunavir.
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Darunavir.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Darunavir.
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Darunavir.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Darunavir.
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Darunavir.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Darunavir.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Darunavir.
DronedaroneThe serum concentration of Dronedarone can be increased when it is combined with Darunavir.
DutasterideThe serum concentration of Dutasteride can be increased when it is combined with Darunavir.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Darunavir.
EfavirenzThe serum concentration of Efavirenz can be increased when it is combined with Darunavir.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Darunavir.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Darunavir.
ElvitegravirThe serum concentration of Elvitegravir can be increased when it is combined with Darunavir.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Darunavir.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Darunavir.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Darunavir.
EstazolamThe serum concentration of Estazolam can be increased when it is combined with Darunavir.
EtizolamThe serum concentration of Etizolam can be increased when it is combined with Darunavir.
EtonogestrelThe serum concentration of Etonogestrel can be decreased when it is combined with Darunavir.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Darunavir.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Darunavir.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Darunavir.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Darunavir.
FlecainideThe serum concentration of Flecainide can be increased when it is combined with Darunavir.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Darunavir.
FluconazoleThe metabolism of Darunavir can be decreased when combined with Fluconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Darunavir.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Darunavir.
FluoxetineThe serum concentration of Fluoxetine can be increased when it is combined with Darunavir.
FluphenazineThe serum concentration of Fluphenazine can be increased when it is combined with Darunavir.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Darunavir.
FluvoxamineThe serum concentration of Fluvoxamine can be increased when it is combined with Darunavir.
FosphenytoinThe serum concentration of Darunavir can be decreased when it is combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Darunavir can be increased when it is combined with Fusidic Acid.
GarlicThe serum concentration of Darunavir can be decreased when it is combined with Garlic.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Darunavir.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Darunavir.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Darunavir.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Darunavir.
GuanfacineThe serum concentration of Guanfacine can be increased when it is combined with Darunavir.
HalofantrineThe serum concentration of Halofantrine can be increased when it is combined with Darunavir.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Darunavir.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Darunavir.
IdelalisibThe serum concentration of Darunavir can be increased when it is combined with Idelalisib.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Darunavir resulting in a loss in efficacy.
IloperidoneThe serum concentration of the active metabolites of Iloperidone can be increased when Iloperidone is used in combination with Darunavir.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Darunavir.
ImidafenacinThe serum concentration of Imidafenacin can be increased when it is combined with Darunavir.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Darunavir.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Darunavir.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Darunavir.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Darunavir.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Darunavir.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Darunavir.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Darunavir.
IrinotecanThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Darunavir.
IsavuconazoniumThe serum concentration of the active metabolites of Isavuconazonium can be increased when Isavuconazonium is used in combination with Darunavir.
IsoflurophateThe serum concentration of Darunavir can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Itraconazole can be increased when it is combined with Darunavir.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Darunavir.
IvacaftorThe serum concentration of Ivacaftor can be increased when it is combined with Darunavir.
IxabepiloneThe serum concentration of Ixabepilone can be increased when it is combined with Darunavir.
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Darunavir.
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Darunavir.
LapatinibThe serum concentration of Lapatinib can be increased when it is combined with Darunavir.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Darunavir.
LercanidipineThe serum concentration of Lercanidipine can be increased when it is combined with Darunavir.
LevobupivacaineThe serum concentration of Levobupivacaine can be increased when it is combined with Darunavir.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Darunavir.
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Darunavir.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Darunavir.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Darunavir.
LopinavirThe serum concentration of Darunavir can be decreased when it is combined with Lopinavir.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Darunavir.
LuliconazoleThe serum concentration of Darunavir can be increased when it is combined with Luliconazole.
LumefantrineThe serum concentration of Lumefantrine can be increased when it is combined with Darunavir.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Darunavir.
MacitentanThe serum concentration of MACITENTAN can be increased when it is combined with Darunavir.
MaprotilineThe serum concentration of Maprotiline can be increased when it is combined with Darunavir.
MaravirocThe serum concentration of Maraviroc can be increased when it is combined with Darunavir.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be decreased when it is combined with Darunavir.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Darunavir.
MethadoneThe serum concentration of Methadone can be decreased when it is combined with Darunavir.
MethamphetamineThe serum concentration of Methamphetamine can be increased when it is combined with Darunavir.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Darunavir.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Darunavir.
MexiletineThe serum concentration of Mexiletine can be increased when it is combined with Darunavir.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Darunavir.
MifepristoneThe serum concentration of Mifepristone can be increased when it is combined with Darunavir.
MitotaneThe serum concentration of Darunavir can be decreased when it is combined with Mitotane.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Darunavir.
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Darunavir.
NelfinavirThe metabolism of Darunavir can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Darunavir can be increased when it is combined with Netupitant.
NevirapineThe serum concentration of Nevirapine can be increased when it is combined with Darunavir.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Darunavir.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Darunavir.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Darunavir.
NisoldipineThe serum concentration of Nisoldipine can be increased when it is combined with Darunavir.
NorethisteroneThe serum concentration of Norethindrone can be decreased when it is combined with Darunavir.
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Darunavir.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Darunavir.
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Darunavir.
OxybutyninThe serum concentration of Oxybutynin can be increased when it is combined with Darunavir.
OxycodoneThe risk or severity of adverse effects can be increased when Darunavir is combined with Oxycodone.
PalbociclibThe serum concentration of Palbociclib can be increased when it is combined with Darunavir.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Darunavir.
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Darunavir.
ParicalcitolThe serum concentration of Paricalcitol can be increased when it is combined with Darunavir.
ParoxetineThe serum concentration of Paroxetine can be decreased when it is combined with Darunavir.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Darunavir.
PerphenazineThe serum concentration of Perphenazine can be increased when it is combined with Darunavir.
PethidineThe risk or severity of adverse effects can be increased when Darunavir is combined with Pethidine.
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Darunavir.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Darunavir.
PimecrolimusThe metabolism of Pimecrolimus can be decreased when combined with Darunavir.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Darunavir.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Darunavir.
PranlukastThe serum concentration of Pranlukast can be increased when it is combined with Darunavir.
PrasugrelThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Darunavir resulting in a loss in efficacy.
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Darunavir.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Darunavir.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Darunavir.
PrimaquineThe serum concentration of Primaquine can be increased when it is combined with Darunavir.
ProcainamideThe serum concentration of Procainamide can be increased when it is combined with Darunavir.
PromazineThe serum concentration of Promazine can be increased when it is combined with Darunavir.
PromethazineThe serum concentration of Promethazine can be increased when it is combined with Darunavir.
PropafenoneThe serum concentration of Propafenone can be increased when it is combined with Darunavir.
PropranololThe serum concentration of Propranolol can be increased when it is combined with Darunavir.
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Darunavir.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Darunavir.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Darunavir.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Darunavir.
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Darunavir.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Darunavir.
RegorafenibThe serum concentration of Regorafenib can be increased when it is combined with Darunavir.
RepaglinideThe serum concentration of Repaglinide can be increased when it is combined with Darunavir.
RetapamulinThe serum concentration of Retapamulin can be increased when it is combined with Darunavir.
RifabutinThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Darunavir.
RifampicinThe serum concentration of Darunavir can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Darunavir can be decreased when it is combined with Rifapentine.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Darunavir.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Darunavir.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Darunavir.
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Darunavir.
RitonavirThe serum concentration of Darunavir can be decreased when it is combined with Ritonavir.
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Darunavir.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Darunavir.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Darunavir.
RuxolitinibThe serum concentration of Ruxolitinib can be increased when it is combined with Darunavir.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Darunavir.
SaquinavirThe serum concentration of Darunavir can be decreased when it is combined with Saquinavir.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Darunavir.
SertralineThe serum concentration of Sertraline can be decreased when it is combined with Darunavir.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Darunavir.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Darunavir.
SiltuximabThe serum concentration of Darunavir can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Darunavir.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Darunavir.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Darunavir.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Darunavir.
St. John's WortThe metabolism of Darunavir can be increased when combined with St. John's Wort.
StiripentolThe serum concentration of Darunavir can be increased when it is combined with Stiripentol.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Darunavir.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Darunavir.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Darunavir.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Darunavir.
TasimelteonThe serum concentration of Tasimelteon can be increased when it is combined with Darunavir.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Darunavir.
TemsirolimusThe risk or severity of adverse effects can be increased when Darunavir is combined with Temsirolimus.
TenofovirThe serum concentration of Darunavir can be increased when it is combined with Tenofovir.
TerfenadineThe serum concentration of Terfenadine can be increased when it is combined with Darunavir.
TetrabenazineThe serum concentration of Tetrabenazine can be increased when it is combined with Darunavir.
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Darunavir.
TicagrelorThe serum concentration of the active metabolites of Ticagrelor can be reduced when Ticagrelor is used in combination with Darunavir resulting in a loss in efficacy.
TimololThe serum concentration of Timolol can be increased when it is combined with Darunavir.
TipranavirThe serum concentration of Darunavir can be decreased when it is combined with Tipranavir.
TocilizumabThe serum concentration of Darunavir can be decreased when it is combined with Tocilizumab.
TofacitinibThe serum concentration of Tofacitinib can be increased when it is combined with Darunavir.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Darunavir.
TolterodineThe serum concentration of Tolterodine can be increased when it is combined with Darunavir.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Darunavir.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Darunavir.
ToremifeneThe risk or severity of adverse effects can be increased when Darunavir is combined with Toremifene.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Darunavir.
TramadolThe serum concentration of Tramadol can be increased when it is combined with Darunavir.
Trastuzumab emtansineThe serum concentration of the active metabolites of ado-trastuzumab emtansine can be increased when ado-trastuzumab emtansine is used in combination with Darunavir.
TrazodoneThe serum concentration of Trazodone can be increased when it is combined with Darunavir.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Darunavir.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Darunavir.
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Darunavir.
VardenafilThe serum concentration of Vardenafil can be increased when it is combined with Darunavir.
VemurafenibThe serum concentration of Vemurafenib can be increased when it is combined with Darunavir.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Darunavir.
VilazodoneThe serum concentration of Vilazodone can be increased when it is combined with Darunavir.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Darunavir.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Darunavir.
VindesineThe serum concentration of Vindesine can be increased when it is combined with Darunavir.
VorapaxarThe serum concentration of Vorapaxar can be increased when it is combined with Darunavir.
VoriconazoleThe serum concentration of Voriconazole can be decreased when it is combined with Darunavir.
VortioxetineThe serum concentration of Vortioxetine can be increased when it is combined with Darunavir.
WarfarinThe serum concentration of Warfarin can be decreased when it is combined with Darunavir.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Darunavir.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Darunavir.
ZuclopenthixolThe serum concentration of Zuclopenthixol can be increased when it is combined with Darunavir.
Food Interactions
  • Take with food - better absorption (+30%).

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
yes
Actions
inhibitor
General Function:
Aspartic-type endopeptidase activity
Specific Function:
Not Available
Gene Name:
pol
Uniprot ID:
Q72874
Molecular Weight:
10778.7 Da
References
  1. Dierynck I, De Wit M, Gustin E, Keuleers I, Vandersmissen J, Hallenberger S, Hertogs K: Binding kinetics of darunavir to human immunodeficiency virus type 1 protease explain the potent antiviral activity and high genetic barrier. J Virol. 2007 Dec;81(24):13845-51. Epub 2007 Oct 10. [PubMed:17928344 ]
  2. Ghosh AK, Dawson ZL, Mitsuya H: Darunavir, a conceptually new HIV-1 protease inhibitor for the treatment of drug-resistant HIV. Bioorg Med Chem. 2007 Dec 15;15(24):7576-80. Epub 2007 Sep 14. [PubMed:17900913 ]
  3. Wang YF, Tie Y, Boross PI, Tozser J, Ghosh AK, Harrison RW, Weber IT: Potent new antiviral compound shows similar inhibition and structural interactions with drug resistant mutants and wild type HIV-1 protease. J Med Chem. 2007 Sep 6;50(18):4509-15. Epub 2007 Aug 16. [PubMed:17696515 ]
  4. McKeage K, Perry CM, Keam SJ: Darunavir: a review of its use in the management of HIV infection in adults. Drugs. 2009;69(4):477-503. doi: 10.2165/00003495-200969040-00007. [PubMed:19323590 ]
  5. Tremblay CL: Combating HIV resistance - focus on darunavir. Ther Clin Risk Manag. 2008 Aug;4(4):759-66. [PubMed:19209258 ]
  6. Kovalevsky AY, Tie Y, Liu F, Boross PI, Wang YF, Leshchenko S, Ghosh AK, Harrison RW, Weber IT: Effectiveness of nonpeptide clinical inhibitor TMC-114 on HIV-1 protease with highly drug resistant mutations D30N, I50V, and L90M. J Med Chem. 2006 Feb 23;49(4):1379-87. [PubMed:16480273 ]
  7. De Meyer S, Azijn H, Surleraux D, Jochmans D, Tahri A, Pauwels R, Wigerinck P, de Bethune MP: TMC114, a novel human immunodeficiency virus type 1 protease inhibitor active against protease inhibitor-resistant viruses, including a broad range of clinical isolates. Antimicrob Agents Chemother. 2005 Jun;49(6):2314-21. [PubMed:15917527 ]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. McKeage K, Perry CM, Keam SJ: Darunavir: a review of its use in the management of HIV infection in adults. Drugs. 2009;69(4):477-503. doi: 10.2165/00003495-200969040-00007. [PubMed:19323590 ]
  2. Tremblay CL: Combating HIV resistance - focus on darunavir. Ther Clin Risk Manag. 2008 Aug;4(4):759-66. [PubMed:19209258 ]
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Drug created on May 16, 2007 11:43 / Updated on June 26, 2016 03:07