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Identification
NameTipranavir
Accession NumberDB00932  (APRD01306)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Tipranavir is a sulfonamide-containing dyhydropyrone and a nonpeptidic protease inhibitor that targets the HIV protease. It is administered with ritonavir in combination therapy to treat HIV infections.

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aptivussolution100 mg/mLoralBoehringer Ingelheim Pharmaceuticals, Inc.2008-09-01Not applicableUs
Aptivuscapsule250 mgoralBoehringer Ingelheim (Canada) Ltd Ltee2005-12-01Not applicableCanada
Aptivuscapsule, liquid filled250 mg/1oralBoehringer Ingelheim Pharmaceuticals, Inc.2005-07-01Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Tipranavir disodium
191150-83-1
Thumb
  • InChI Key: ZBWMQTUSVWBMQE-KPHXKKTMSA-M
  • Monoisotopic Mass: 646.17011633
  • Average Mass: 646.63
DBSALT001882
Categories
UNIIZZT404XD09
CAS number174484-41-4
WeightAverage: 602.664
Monoisotopic: 602.206227481
Chemical FormulaC31H33F3N2O5S
InChI KeySUJUHGSWHZTSEU-FYBSXPHGSA-N
InChI
InChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1
IUPAC Name
N-{3-[(1R)-1-[(6R)-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-5,6-dihydro-2H-pyran-3-yl]propyl]phenyl}-5-(trifluoromethyl)pyridine-2-sulfonamide
SMILES
[H][C@@](CC)(C1=CC(NS(=O)(=O)C2=NC=C(C=C2)C(F)(F)F)=CC=C1)C1=C(O)C[C@@](CCC)(CCC2=CC=CC=C2)OC1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentLinear diarylheptanoids
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
  • Sulfanilide
  • Pyridine-2-sulfonamide
  • Phenylpropane
  • Dihydropyranone
  • Benzenoid
  • Pyridine
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor combination antiretroviral treatment of HIV-1 infected adult patients with evidence of viral replication, who are highly treatment-experienced or have HIV-1 strains resistant to multiple protease inhibitors.
PharmacodynamicsTipranavir is a non-peptidic protease inhibitor (PI) of HIV. Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Nelfinavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.
Mechanism of actionTipranavir (TPV) is a non-peptidic HIV-1 protease inhibitor that inhibits the processing of the viral Gag and Gag-Pol polyproteins in HIV-1 infected cells, thus preventing formation of mature virions. Two mechanisms are suggested in regards to the potency of tipranavir: 1. Tipravanir may bind to the active site of the protease enzyme with fewer hydrogen bonds than peptidic protease inhibitors, which results in increased flexibility, allowing it to fit into the active site of the enzyme in viruses that have become resistance to other protease inhibitors. This also enables tipranavir to adjust to amino acid substitutions at the active site. 2. Tipranavir's strong hydrogen bonding interaction with the amide backbone of the protease active site Asp30 may lead to its activity against resistant viruses.
Related Articles
AbsorptionAbsorption is limited, although no absolute quantification of absorption is available.
Volume of distributionNot Available
Protein bindingExtensive (> 99.9%), to both human serum albumin and α-1-acid glycoprotein.
Metabolism

Hepatic. In vitro metabolism studies with human liver microsomes indicated that CYP 3A4 is the predominant CYP enzyme involved in tipranavir metabolism.

Route of eliminationNot Available
Half life5-6 hours
ClearanceNot Available
ToxicityOral LD50 in rat is over 5,000 mg/kg. Side effects include thirst and hunger, unexplained weight loss, increased urination, fatigue, and dry, itchy skin.
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+0.9066
Blood Brain Barrier-0.6801
Caco-2 permeable-0.6103
P-glycoprotein substrateSubstrate0.5277
P-glycoprotein inhibitor INon-inhibitor0.5057
P-glycoprotein inhibitor IINon-inhibitor0.9249
Renal organic cation transporterNon-inhibitor0.9277
CYP450 2C9 substrateNon-substrate0.8364
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5143
CYP450 1A2 substrateNon-inhibitor0.6708
CYP450 2C9 inhibitorNon-inhibitor0.5711
CYP450 2D6 inhibitorNon-inhibitor0.8485
CYP450 2C19 inhibitorNon-inhibitor0.5383
CYP450 3A4 inhibitorNon-inhibitor0.5442
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5317
Ames testNon AMES toxic0.6078
CarcinogenicityNon-carcinogens0.728
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5773 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8277
hERG inhibition (predictor II)Non-inhibitor0.702
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Boehringer ingelheim pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral250 mg
Capsule, liquid filledoral250 mg/1
Solutionoral100 mg/mL
Prices
Unit descriptionCostUnit
Aptivus 120 250 mg capsule Bottle1271.8USD bottle
Aptivus 250 mg capsule10.19USD capsule
Aptivus 100 mg/ml solution4.29USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2187523 No2006-11-212015-05-04Canada
CA2294033 No2007-01-092018-07-27Canada
US5852195 Yes1999-12-222019-12-22Us
US6147095 Yes2000-04-292020-04-29Us
US6169181 No1994-05-062014-05-06Us
US6231887 Yes1999-01-272019-01-27Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityInsolubleNot Available
logP6.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000205 mg/mLALOGPS
logP6.29ALOGPS
logP7.14ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)5.92ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.59 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity154.57 m3·mol-1ChemAxon
Polarizability60.87 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Franz Klingler, “Enantioselective hydrogenation of intermediates in the synthesis of tipranavir.” U.S. Patent US20040224990, issued November 11, 2004.

US20040224990
General References
  1. Doyon L, Tremblay S, Bourgon L, Wardrop E, Cordingley MG: Selection and characterization of HIV-1 showing reduced susceptibility to the non-peptidic protease inhibitor tipranavir. Antiviral Res. 2005 Oct;68(1):27-35. [PubMed:16122817 ]
  2. Authors unspecified: Tipranavir: PNU 140690, tipranivir. Drugs R D. 2006;7(1):55-62. [PubMed:16620137 ]
  3. Temesgen Z, Feinberg J: Tipranavir: a new option for the treatment of drug-resistant HIV infection. Clin Infect Dis. 2007 Sep 15;45(6):761-9. Epub 2007 Aug 7. [PubMed:17712762 ]
  4. Luna B, Townsend MU: Tipranavir: the first nonpeptidic protease inhibitor for the treatment of protease resistance. Clin Ther. 2007 Nov;29(11):2309-18. [PubMed:18158073 ]
External Links
ATC CodesJ05AE09
AHFS Codes
  • 08:18.08.08
PDB EntriesNot Available
FDA labelDownload (388 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Tipranavir.
AbciximabTipranavir may increase the antiplatelet activities of Abciximab.
AcenocoumarolTipranavir may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Tipranavir.
Acetylsalicylic acidTipranavir may increase the antiplatelet activities of Acetylsalicylic acid.
AfatinibThe serum concentration of Afatinib can be decreased when it is combined with Tipranavir.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Tipranavir.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Tipranavir.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Tipranavir.
AmiodaroneThe serum concentration of Amiodarone can be increased when it is combined with Tipranavir.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Tipranavir.
AnagrelideTipranavir may increase the antiplatelet activities of Anagrelide.
ApixabanTipranavir may increase the anticoagulant activities of Apixaban.
ArgatrobanTipranavir may increase the anticoagulant activities of Argatroban.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Tipranavir.
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Tipranavir.
AtomoxetineThe serum concentration of Atomoxetine can be increased when it is combined with Tipranavir.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Tipranavir.
BatimastatThe serum concentration of Batimastat can be decreased when it is combined with Tipranavir.
BepridilThe serum concentration of Bepridil can be increased when it is combined with Tipranavir.
BexaroteneThe serum concentration of Tipranavir can be decreased when it is combined with Bexarotene.
BivalirudinTipranavir may increase the anticoagulant activities of Bivalirudin.
BoceprevirThe serum concentration of Boceprevir can be decreased when it is combined with Tipranavir.
BosentanThe serum concentration of Tipranavir can be decreased when it is combined with Bosentan.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Tipranavir.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Tipranavir.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Tipranavir.
CangrelorTipranavir may increase the antiplatelet activities of Cangrelor.
CarbamazepineThe metabolism of Tipranavir can be increased when combined with Carbamazepine.
ChlorotrianiseneChlorotrianisene may increase the dermatologic adverse activities of Tipranavir.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Tipranavir.
Cholic AcidTipranavir may decrease the excretion rate of Cholic Acid which could result in a lower serum level and potentially a reduction in efficacy.
CilostazolTipranavir may increase the antiplatelet activities of Cilostazol.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Tipranavir.
CitalopramTipranavir may increase the antiplatelet activities of Citalopram.
Citric AcidTipranavir may increase the anticoagulant activities of Citric Acid.
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Tipranavir.
ClopidogrelTipranavir may increase the antiplatelet activities of Clopidogrel.
CodeineThe therapeutic efficacy of Codeine can be decreased when used in combination with Tipranavir.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Tipranavir.
CyclophosphamideThe risk or severity of adverse effects can be increased when Tipranavir is combined with Cyclophosphamide.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Tipranavir.
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be decreased when it is combined with Tipranavir.
DabrafenibThe serum concentration of Tipranavir can be decreased when it is combined with Dabrafenib.
DalteparinTipranavir may increase the anticoagulant activities of Dalteparin.
DanaparoidTipranavir may increase the anticoagulant activities of Danaparoid.
DarunavirThe serum concentration of Darunavir can be decreased when it is combined with Tipranavir.
DeferasiroxThe serum concentration of Tipranavir can be decreased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Tipranavir.
DesirudinTipranavir may increase the anticoagulant activities of Desirudin.
DesvenlafaxineTipranavir may increase the antiplatelet activities of Desvenlafaxine.
DiclofenacTipranavir may increase the antiplatelet activities of Diclofenac.
DicoumarolTipranavir may increase the anticoagulant activities of Dicoumarol.
DidanosineThe serum concentration of Didanosine can be decreased when it is combined with Tipranavir.
DienogestThe serum concentration of Dienogest can be increased when it is combined with Tipranavir.
DiflunisalTipranavir may increase the antiplatelet activities of Diflunisal.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Tipranavir.
DipyridamoleTipranavir may increase the antiplatelet activities of Dipyridamole.
DisulfiramThe risk or severity of adverse effects can be increased when Disulfiram is combined with Tipranavir.
DolutegravirThe serum concentration of Dolutegravir can be decreased when it is combined with Tipranavir.
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Tipranavir.
DuloxetineTipranavir may increase the antiplatelet activities of Duloxetine.
Edetic AcidTipranavir may increase the anticoagulant activities of Edetic Acid.
EdoxabanTipranavir may increase the anticoagulant activities of Edoxaban.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Tipranavir.
EluxadolineThe serum concentration of Eluxadoline can be increased when it is combined with Tipranavir.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Tipranavir.
EnoxaparinTipranavir may increase the anticoagulant activities of Enoxaparin.
EptifibatideTipranavir may increase the antiplatelet activities of Eptifibatide.
EscitalopramTipranavir may increase the antiplatelet activities of Escitalopram.
EsomeprazoleThe serum concentration of Esomeprazole can be decreased when it is combined with Tipranavir.
EstradiolEstradiol may increase the dermatologic adverse activities of Tipranavir.
Estrone sulfateEstropipate may increase the dermatologic adverse activities of Tipranavir.
Ethyl biscoumacetateTipranavir may increase the anticoagulant activities of Ethyl biscoumacetate.
EtodolacTipranavir may increase the antiplatelet activities of Etodolac.
EtonogestrelThe serum concentration of Etonogestrel can be increased when it is combined with Tipranavir.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Tipranavir.
FenoprofenTipranavir may increase the antiplatelet activities of Fenoprofen.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Tipranavir.
FlecainideThe serum concentration of Flecainide can be increased when it is combined with Tipranavir.
FloctafenineTipranavir may increase the antiplatelet activities of Floctafenine.
FluconazoleThe serum concentration of Tipranavir can be increased when it is combined with Fluconazole.
FlurbiprofenTipranavir may increase the antiplatelet activities of Flurbiprofen.
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Tipranavir.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Tipranavir.
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Tipranavir.
Fondaparinux sodiumTipranavir may increase the anticoagulant activities of Fondaparinux sodium.
FosamprenavirThe serum concentration of Fosamprenavir can be decreased when it is combined with Tipranavir.
FosphenytoinThe serum concentration of Tipranavir can be decreased when it is combined with Fosphenytoin.
GarlicThe serum concentration of Tipranavir can be decreased when it is combined with Garlic.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Tipranavir.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Tipranavir.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Tipranavir.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Tipranavir.
HeparinTipranavir may increase the anticoagulant activities of Heparin.
HydrocodoneThe serum concentration of the active metabolites of Hydrocodone can be reduced when Hydrocodone is used in combination with Tipranavir resulting in a loss in efficacy.
IbuprofenTipranavir may increase the antiplatelet activities of Ibuprofen.
IloperidoneThe serum concentration of the active metabolites of Iloperidone can be increased when Iloperidone is used in combination with Tipranavir.
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Tipranavir.
IndomethacinTipranavir may increase the antiplatelet activities of Indomethacin.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Tipranavir.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Tipranavir.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Tipranavir.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Tipranavir.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Tipranavir.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Tipranavir.
IsoflurophateThe serum concentration of Isoflurophate can be decreased when it is combined with Tipranavir.
ItraconazoleThe serum concentration of Itraconazole can be increased when it is combined with Tipranavir.
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Tipranavir.
KetoprofenTipranavir may increase the antiplatelet activities of Ketoprofen.
KetorolacTipranavir may increase the antiplatelet activities of Ketorolac.
LansoprazoleThe serum concentration of Lansoprazole can be decreased when it is combined with Tipranavir.
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Tipranavir.
LevomilnacipranTipranavir may increase the antiplatelet activities of Levomilnacipran.
LevonorgestrelThe serum concentration of Levonorgestrel can be increased when it is combined with Tipranavir.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Tipranavir.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Tipranavir.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Tipranavir.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be increased when it is combined with Tipranavir.
Mefenamic acidTipranavir may increase the antiplatelet activities of Mefenamic acid.
MeloxicamTipranavir may increase the antiplatelet activities of Meloxicam.
MequitazineThe serum concentration of Mequitazine can be increased when it is combined with Tipranavir.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Tipranavir.
MethadoneThe serum concentration of Methadone can be decreased when it is combined with Tipranavir.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Tipranavir.
MetronidazoleThe risk or severity of adverse effects can be increased when Metronidazole is combined with Tipranavir.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Tipranavir.
MilnacipranTipranavir may increase the antiplatelet activities of Milnacipran.
MitotaneThe serum concentration of Tipranavir can be decreased when it is combined with Mitotane.
NabumetoneTipranavir may increase the antiplatelet activities of Nabumetone.
NadroparinTipranavir may increase the anticoagulant activities of Nadroparin.
NaproxenTipranavir may increase the antiplatelet activities of Naproxen.
NebivololThe serum concentration of Nebivolol can be increased when it is combined with Tipranavir.
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Tipranavir.
NelfinavirThe serum concentration of Nelfinavir can be decreased when it is combined with Tipranavir.
NorethisteroneThe serum concentration of Norethindrone can be increased when it is combined with Tipranavir.
OmeprazoleThe serum concentration of Omeprazole can be decreased when it is combined with Tipranavir.
OxaprozinTipranavir may increase the antiplatelet activities of Oxaprozin.
PantoprazoleThe serum concentration of Pantoprazole can be decreased when it is combined with Tipranavir.
PethidineThe risk or severity of adverse effects can be increased when Tipranavir is combined with Pethidine.
PhenindioneTipranavir may increase the anticoagulant activities of Phenindione.
PhenobarbitalThe serum concentration of Tipranavir can be decreased when it is combined with Phenobarbital.
PhenprocoumonTipranavir may increase the anticoagulant activities of Phenprocoumon.
PhenytoinThe serum concentration of Tipranavir can be decreased when it is combined with Phenytoin.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Tipranavir.
PiroxicamTipranavir may increase the antiplatelet activities of Piroxicam.
PrasugrelTipranavir may increase the antiplatelet activities of Prasugrel.
PropafenoneThe serum concentration of Propafenone can be increased when it is combined with Tipranavir.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Tipranavir.
RabeprazoleThe serum concentration of Rabeprazole can be decreased when it is combined with Tipranavir.
RaltegravirThe serum concentration of Raltegravir can be decreased when it is combined with Tipranavir.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Tipranavir.
RifabutinThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Tipranavir.
RifampicinThe serum concentration of Tipranavir can be decreased when it is combined with Rifampicin.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Tipranavir.
RivaroxabanTipranavir may increase the anticoagulant activities of Rivaroxaban.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Tipranavir.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Tipranavir.
SaquinavirThe serum concentration of Saquinavir can be decreased when it is combined with Tipranavir.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Tipranavir.
SertralineTipranavir may increase the antiplatelet activities of Sertraline.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Tipranavir.
SiltuximabThe serum concentration of Tipranavir can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Tipranavir.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Tipranavir.
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Tipranavir.
St. John's WortThe serum concentration of Tipranavir can be decreased when it is combined with St. John's Wort.
SulindacTipranavir may increase the antiplatelet activities of Sulindac.
SulodexideTipranavir may increase the anticoagulant activities of Sulodexide.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Tipranavir.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Tipranavir.
TamoxifenThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Tipranavir resulting in a loss in efficacy.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Tipranavir.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Tipranavir.
TemsirolimusThe risk or severity of adverse effects can be increased when Tipranavir is combined with Temsirolimus.
TenofovirThe serum concentration of Tipranavir can be decreased when it is combined with Tenofovir.
TetrabenazineThe serum concentration of Tetrabenazine can be increased when it is combined with Tipranavir.
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Tipranavir.
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Tipranavir.
Tiaprofenic acidTipranavir may increase the antiplatelet activities of Tiaprofenic acid.
TicagrelorTipranavir may increase the antiplatelet activities of Ticagrelor.
TiclopidineTipranavir may increase the antiplatelet activities of Ticlopidine.
TinzaparinTipranavir may increase the anticoagulant activities of Tinzaparin.
TirofibanTipranavir may increase the antiplatelet activities of Tirofiban.
TocilizumabThe serum concentration of Tipranavir can be decreased when it is combined with Tocilizumab.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Tipranavir.
TolmetinTipranavir may increase the antiplatelet activities of Tolmetin.
TramadolThe therapeutic efficacy of Tramadol can be decreased when used in combination with Tipranavir.
TrazodoneThe serum concentration of Trazodone can be increased when it is combined with Tipranavir.
TreprostinilTipranavir may increase the anticoagulant activities of Treprostinil.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Tipranavir.
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Tipranavir.
VerapamilThe serum concentration of Verapamil can be decreased when it is combined with Tipranavir.
VilazodoneTipranavir may increase the antiplatelet activities of Vilazodone.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Tipranavir.
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Tipranavir.
Vitamin EThe risk or severity of adverse effects can be increased when Tipranavir is combined with Vitamin E.
VorapaxarTipranavir may increase the antiplatelet activities of Vorapaxar.
VortioxetineThe serum concentration of Vortioxetine can be increased when it is combined with Tipranavir.
WarfarinTipranavir may increase the anticoagulant activities of Warfarin.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Tipranavir.
Food InteractionsNot Available

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. 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 ]
  2. Tenore SB, Ferreira PR: The Place of protease inhibitors in antiretroviral treatment. Braz J Infect Dis. 2009 Oct;13(5):371-4. doi: 10.1590/S1413-86702009000500012. [PubMed:20428639 ]
  3. Muzammil S, Armstrong AA, Kang LW, Jakalian A, Bonneau PR, Schmelmer V, Amzel LM, Freire E: Unique thermodynamic response of tipranavir to human immunodeficiency virus type 1 protease drug resistance mutations. J Virol. 2007 May;81(10):5144-54. Epub 2007 Mar 14. [PubMed:17360759 ]
  4. Hsieh SM, Chang SY, Hung CC, Sheng WH, Chen MY, Chang SC: Impact of first-line protease inhibitors on predicted resistance to tipranavir in HIV-1-infected patients with virological failure. BMC Infect Dis. 2009 Sep 14;9:154. doi: 10.1186/1471-2334-9-154. [PubMed:19751502 ]
  5. Temesgen Z, Feinberg J: Tipranavir: a new option for the treatment of drug-resistant HIV infection. Clin Infect Dis. 2007 Sep 15;45(6):761-9. Epub 2007 Aug 7. [PubMed:17712762 ]
  6. Luna B, Townsend MU: Tipranavir: the first nonpeptidic protease inhibitor for the treatment of protease resistance. Clin Ther. 2007 Nov;29(11):2309-18. [PubMed:18158073 ]
  7. Croom KF, Keam SJ: Tipranavir: a ritonavir-boosted protease inhibitor. Drugs. 2005;65(12):1669-77; discussion 1678-9. [PubMed:16060700 ]
  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. Temesgen Z, Feinberg J: Tipranavir: a new option for the treatment of drug-resistant HIV infection. Clin Infect Dis. 2007 Sep 15;45(6):761-9. Epub 2007 Aug 7. [PubMed:17712762 ]
  2. Luna B, Townsend MU: Tipranavir: the first nonpeptidic protease inhibitor for the treatment of protease resistance. Clin Ther. 2007 Nov;29(11):2309-18. [PubMed:18158073 ]
  3. Li F, Wang L, Guo GL, Ma X: Metabolism-mediated drug interactions associated with ritonavir-boosted tipranavir in mice. Drug Metab Dispos. 2010 May;38(5):871-8. doi: 10.1124/dmd.109.030817. Epub 2010 Jan 26. [PubMed:20103582 ]
  4. Dumond JB, Vourvahis M, Rezk NL, Patterson KB, Tien HC, White N, Jennings SH, Choi SO, Li J, Wagner MJ, La-Beck NM, Drulak M, Sabo JP, Castles MA, Macgregor TR, Kashuba AD: A phenotype-genotype approach to predicting CYP450 and P-glycoprotein drug interactions with the mixed inhibitor/inducer tipranavir/ritonavir. Clin Pharmacol Ther. 2010 Jun;87(6):735-42. doi: 10.1038/clpt.2009.253. Epub 2010 Feb 10. [PubMed:20147896 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Li F, Wang L, Guo GL, Ma X: Metabolism-mediated drug interactions associated with ritonavir-boosted tipranavir in mice. Drug Metab Dispos. 2010 May;38(5):871-8. doi: 10.1124/dmd.109.030817. Epub 2010 Jan 26. [PubMed:20103582 ]
  2. Dumond JB, Vourvahis M, Rezk NL, Patterson KB, Tien HC, White N, Jennings SH, Choi SO, Li J, Wagner MJ, La-Beck NM, Drulak M, Sabo JP, Castles MA, Macgregor TR, Kashuba AD: A phenotype-genotype approach to predicting CYP450 and P-glycoprotein drug interactions with the mixed inhibitor/inducer tipranavir/ritonavir. Clin Pharmacol Ther. 2010 Jun;87(6):735-42. doi: 10.1038/clpt.2009.253. Epub 2010 Feb 10. [PubMed:20147896 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Li F, Wang L, Guo GL, Ma X: Metabolism-mediated drug interactions associated with ritonavir-boosted tipranavir in mice. Drug Metab Dispos. 2010 May;38(5):871-8. doi: 10.1124/dmd.109.030817. Epub 2010 Jan 26. [PubMed:20103582 ]
  2. Dumond JB, Vourvahis M, Rezk NL, Patterson KB, Tien HC, White N, Jennings SH, Choi SO, Li J, Wagner MJ, La-Beck NM, Drulak M, Sabo JP, Castles MA, Macgregor TR, Kashuba AD: A phenotype-genotype approach to predicting CYP450 and P-glycoprotein drug interactions with the mixed inhibitor/inducer tipranavir/ritonavir. Clin Pharmacol Ther. 2010 Jun;87(6):735-42. doi: 10.1038/clpt.2009.253. Epub 2010 Feb 10. [PubMed:20147896 ]
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Drug created on June 13, 2005 07:24 / Updated on August 24, 2016 03:05