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Identification
NameFosamprenavir
Accession NumberDB01319
TypeSmall Molecule
GroupsApproved
Description

Fosamprenavir is a prodrug of amprenavir, an inhibitor of human immunodeficiency virus (HIV) protease.

Structure
Thumb
Synonyms
Fosamprenavir
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Lexivatablet, film coated700 mg/1oralREMEDYREPACK INC.2013-05-09Not applicableUs
Lexivatablet, film coated700 mg/1oralState of Florida DOH Central Pharmacy2014-11-01Not applicableUs
Lexivatablet, film coated700 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
Lexivasuspension50 mg/mLoralVii V Healthcare Company2010-10-04Not applicableUs
Lexivatablet, film coated700 mg/1oralVii V Healthcare Company2010-10-04Not applicableUs
Telzirsuspension50 mgoralViiv Healthcare Ulc2005-02-23Not applicableCanada
Telzirtablet700 mgoralViiv Healthcare Ulc2004-12-22Not applicableCanada
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
Fosamprenavir calcium
ThumbNot applicableDBSALT001228
Categories
UNIIWOU1621EEG
CAS number226700-79-4
WeightAverage: 585.607
Monoisotopic: 585.190986967
Chemical FormulaC25H36N3O9PS
InChI KeyInChIKey=MLBVMOWEQCZNCC-OEMFJLHTSA-N
InChI
InChI=1S/C25H36N3O9PS/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32)/t21-,23-,24+/m0/s1
IUPAC Name
{[(2R,3S)-1-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid
SMILES
CC(C)CN(C[C@@H](OP(O)(O)=O)[[email protected]](CC1=CC=CC=C1)NC(=O)O[[email protected]]1CCOC1)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
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Aniline
  • Alkyl phosphate
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Oxolane
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationIndicated in combination with other antiretroviral agents for the treatment of human immunodeficiency virus (HIV-1) infection, as well as postexposure prophylaxis of HIV infection in individuals who have had occupational or nonoccupational exposure to potentially infectious body fluids of a person known to be infected with HIV when that exposure represents a substantial risk for HIV transmission. The use of fosamprenavir is pending revision due to a potential association between the drug and myocardial infarction and dyslipidemia in HIV infected adults.
PharmacodynamicsFosamprenavir is a pro-drug of the protease inhibitor and antiretroviral drug amprenavir. It has little or no antiviral activity until it is hydrolyzed by cellular phosphatases into amprenavir, which is the active ingredient. That metabolization increases the duration that amprenavir is available, making fosamprenavir a slow-release version of amprenavir and thus reducing the number of pills required versus standard amprenavir.
Mechanism of actionFosamprenavir is a prodrug that is rapidly hydrolyzed to amprenavir by cellular phosphatases in the gut epithelium as it is absorbed. Amprenavir is an inhibitor of HIV-1 protease. During HIV replication, HIV protease cleaves viral polypeptide products of the Gag and Gag-Pol genes to form structural proteins of the virion core and essential viral enzymes. Amprenavir interferes with this process by binding to the active site of HIV-1 protease, thereby preventing the processing of viral Gag and Gag-Pol polyprotein precursors, resulting in the formation of immature non-infectious viral particles.
Related Articles
AbsorptionThe absolute oral bioavailability of amprenavir after administration of fosamprenavir in humans has not been established. After administration of a single 1,400 mg dose in the fasted state, fosamprenavir oral suspension (50 mg/mL) and fosamprenavir tablets (700 mg) provided similar amprenavir exposures (AUC), however, the Cmax of amprenavir after administration of the suspension formulation was 14.5 % higher compared with the tablet.
Volume of distributionNot Available
Protein bindingVery high (approximately 90%); primarily bound to alpha 1 -acid glycoprotein. Higher amounts of unbound amprenavir present as amprenavir serum concentrations increase.
Metabolism

In the gut epithelium during absorption, fosamprenavir is rapidly and almost completely hydrolyzed to amprenavir and inorganic phosphate prior to reaching the systemic circulation. Amprenavir is metabolized in the liver by the cytochrome P450 3A4 (CYP3A4) enzyme system.

Route of eliminationExcretion of unchanged amprenavir in urine and feces is minimal. The renal elimination of unchanged amprenavir represents approximately 1% of the administered dose; therefore, renal impairment is not expected to significantly impact the elimination of amprenavir. Amprenavir, the active metabolite of fosamprenavir, is metabolized in the liver by the cytochrome P450 enzyme system.
Half lifeThe plasma elimination half-life of amprenavir (the active metabolite) is approximately 7.7 hours.
ClearanceNot Available
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+0.6363
Blood Brain Barrier+0.5379
Caco-2 permeable+0.6992
P-glycoprotein substrateSubstrate0.6482
P-glycoprotein inhibitor IInhibitor0.7374
P-glycoprotein inhibitor IINon-inhibitor0.7819
Renal organic cation transporterNon-inhibitor0.8671
CYP450 2C9 substrateSubstrate0.5877
CYP450 2D6 substrateSubstrate0.6061
CYP450 3A4 substrateSubstrate0.5805
CYP450 1A2 substrateNon-inhibitor0.7454
CYP450 2C9 inhibitorNon-inhibitor0.6627
CYP450 2D6 inhibitorNon-inhibitor0.8835
CYP450 2C19 inhibitorNon-inhibitor0.6591
CYP450 3A4 inhibitorNon-inhibitor0.6317
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6969
Ames testNon AMES toxic0.598
CarcinogenicityNon-carcinogens0.78
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5018 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9846
hERG inhibition (predictor II)Non-inhibitor0.8356
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Suspensionoral50 mg/mL
Tablet, film coatedoral700 mg/1
Suspensionoral50 mg
Tabletoral700 mg
Prices
Unit descriptionCostUnit
Lexiva 700 mg tablet14.78USD 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
CA2231700 No2005-08-092018-03-10Canada
US6436989 Yes1998-06-242018-06-24Us
US6514953 Yes2000-01-152020-01-15Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.685 mg/mLALOGPS
logP0.84ALOGPS
logP1.92ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)2.45ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area177.72 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity144.95 m3·mol-1ChemAxon
Polarizability57.77 Å3ChemAxon
Number of Rings3ChemAxon
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

US6559815
General References
  1. Smith KY, Weinberg WG, Dejesus E, Fischl MA, Liao Q, Ross LL, Pakes GE, Pappa KA, Lancaster CT: Fosamprenavir or atazanavir once daily boosted with ritonavir 100 mg, plus tenofovir/emtricitabine, for the initial treatment of HIV infection: 48-week results of ALERT. AIDS Res Ther. 2008 Mar 28;5:5. doi: 10.1186/1742-6405-5-5. [PubMed:18373851 ]
  2. Hoffman RM, Umeh OC, Garris C, Givens N, Currier JS: Evaluation of sex differences of fosamprenavir (with and without ritonavir) in HIV-infected men and women. HIV Clin Trials. 2007 Nov-Dec;8(6):371-80. [PubMed:18042502 ]
  3. Chapman TM, Plosker GL, Perry CM: Fosamprenavir: a review of its use in the management of antiretroviral therapy-naive patients with HIV infection. Drugs. 2004;64(18):2101-24. [PubMed:15341507 ]
  4. Furfine ES, Baker CT, Hale MR, Reynolds DJ, Salisbury JA, Searle AD, Studenberg SD, Todd D, Tung RD, Spaltenstein A: Preclinical pharmacology and pharmacokinetics of GW433908, a water-soluble prodrug of the human immunodeficiency virus protease inhibitor amprenavir. Antimicrob Agents Chemother. 2004 Mar;48(3):791-8. [PubMed:14982766 ]
  5. Sension M: Initial therapy for human immunodeficiency virus: broadening the options. HIV Clin Trials. 2004 Mar-Apr;5(2):99-111. [PubMed:15116286 ]
  6. Wood R, Arasteh K, Stellbrink HJ, Teofilo E, Raffi F, Pollard RB, Eron J, Yeo J, Millard J, Wire MB, Naderer OJ: Six-week randomized controlled trial to compare the tolerabilities, pharmacokinetics, and antiviral activities of GW433908 and amprenavir in human immunodeficiency virus type 1-infected patients. Antimicrob Agents Chemother. 2004 Jan;48(1):116-23. [PubMed:14693528 ]
  7. Falcoz C, Jenkins JM, Bye C, Hardman TC, Kenney KB, Studenberg S, Fuder H, Prince WT: Pharmacokinetics of GW433908, a prodrug of amprenavir, in healthy male volunteers. J Clin Pharmacol. 2002 Aug;42(8):887-98. [PubMed:12162471 ]
  8. Wire MB, Shelton MJ, Studenberg S: Fosamprenavir : clinical pharmacokinetics and drug interactions of the amprenavir prodrug. Clin Pharmacokinet. 2006;45(2):137-68. [PubMed:16485915 ]
External Links
ATC CodesJ05AE07
AHFS Codes
  • 08:18.08.08
PDB EntriesNot Available
FDA labelDownload (374 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Fosamprenavir.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Fosamprenavir.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Fosamprenavir.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Fosamprenavir.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Fosamprenavir.
AmiodaroneThe serum concentration of Amiodarone can be increased when it is combined with Fosamprenavir.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Fosamprenavir.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Fosamprenavir.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Fosamprenavir.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Fosamprenavir.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Fosamprenavir.
BatimastatThe serum concentration of Fosamprenavir can be increased when it is combined with Batimastat.
BepridilThe metabolism of Bepridil can be decreased when combined with Fosamprenavir.
BexaroteneThe serum concentration of Fosamprenavir can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Fosamprenavir can be decreased when it is combined with Boceprevir.
BosentanThe serum concentration of Fosamprenavir can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Fosamprenavir.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Fosamprenavir.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Fosamprenavir.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Fosamprenavir.
CarbamazepineThe metabolism of Fosamprenavir can be increased when combined with Carbamazepine.
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Fosamprenavir.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Fosamprenavir.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Fosamprenavir.
CimetidineThe serum concentration of Fosamprenavir can be decreased when it is combined with Cimetidine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Fosamprenavir.
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Fosamprenavir.
ClorazepateThe serum concentration of Clorazepate can be increased when it is combined with Fosamprenavir.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Fosamprenavir.
CyclophosphamideThe risk or severity of adverse effects can be increased when Fosamprenavir is combined with Cyclophosphamide.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Fosamprenavir.
DabrafenibThe serum concentration of Fosamprenavir can be decreased when it is combined with Dabrafenib.
DapoxetineThe serum concentration of Dapoxetine can be increased when it is combined with Fosamprenavir.
DeferasiroxThe serum concentration of Fosamprenavir can be decreased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Fosamprenavir.
DexamethasoneThe serum concentration of Fosamprenavir can be decreased when it is combined with Dexamethasone.
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Fosamprenavir.
DienogestThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Dienogest resulting in a loss in efficacy.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Fosamprenavir.
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Fosamprenavir.
DolutegravirThe serum concentration of Dolutegravir can be decreased when it is combined with Fosamprenavir.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Fosamprenavir.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Fosamprenavir.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Fosamprenavir.
EfavirenzThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Efavirenz resulting in a loss in efficacy.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Fosamprenavir.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Fosamprenavir.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Fosamprenavir.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Fosamprenavir.
EtonogestrelThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Etonogestrel resulting in a loss in efficacy.
EtravirineThe serum concentration of the active metabolites of Fosamprenavir can be increased when Fosamprenavir is used in combination with Etravirine.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Fosamprenavir.
FamotidineThe serum concentration of Fosamprenavir can be decreased when it is combined with Famotidine.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Fosamprenavir.
FlecainideThe serum concentration of Flecainide can be increased when it is combined with Fosamprenavir.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Fosamprenavir.
FlunisolideThe metabolism of Flunisolide can be decreased when combined with Fosamprenavir.
FlurazepamThe serum concentration of Flurazepam can be increased when it is combined with Fosamprenavir.
FosphenytoinThe serum concentration of Fosamprenavir can be increased when it is combined with Fosphenytoin.
GarlicThe serum concentration of Fosamprenavir can be decreased when it is combined with Garlic.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Fosamprenavir.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Fosamprenavir.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Fosamprenavir.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Fosamprenavir.
HalofantrineThe serum concentration of Halofantrine can be increased when it is combined with Fosamprenavir.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Fosamprenavir.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Fosamprenavir.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Fosamprenavir resulting in a loss in efficacy.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Fosamprenavir.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Fosamprenavir.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Fosamprenavir.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Fosamprenavir.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Fosamprenavir.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Fosamprenavir.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Fosamprenavir.
IsoflurophateThe serum concentration of Fosamprenavir can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of the active metabolites of Fosamprenavir can be increased when Fosamprenavir is used in combination with Itraconazole.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Fosamprenavir.
IvacaftorThe serum concentration of Ivacaftor can be increased when it is combined with Fosamprenavir.
KetoconazoleThe serum concentration of the active metabolites of Fosamprenavir can be increased when Fosamprenavir is used in combination with Ketoconazole.
LevonorgestrelThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Levonorgestrel resulting in a loss in efficacy.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Fosamprenavir.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Fosamprenavir.
LopinavirThe serum concentration of Lopinavir can be decreased when it is combined with Fosamprenavir.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Fosamprenavir.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Fosamprenavir.
Medroxyprogesterone acetateThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Medroxyprogesterone Acetate resulting in a loss in efficacy.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Fosamprenavir.
MethadoneThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Methadone resulting in a loss in efficacy.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Fosamprenavir.
MitotaneThe serum concentration of Fosamprenavir can be decreased when it is combined with Mitotane.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Fosamprenavir.
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Fosamprenavir.
NevirapineThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Nevirapine resulting in a loss in efficacy.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Fosamprenavir.
NizatidineThe serum concentration of Fosamprenavir can be decreased when it is combined with Nizatidine.
NorethisteroneThe serum concentration of the active metabolites of Fosamprenavir can be reduced when Fosamprenavir is used in combination with Norethindrone resulting in a loss in efficacy.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Fosamprenavir.
OxycodoneThe risk or severity of adverse effects can be increased when Fosamprenavir is combined with Oxycodone.
ParoxetineThe serum concentration of Paroxetine can be decreased when it is combined with Fosamprenavir.
PethidineThe risk or severity of adverse effects can be increased when Fosamprenavir is combined with Pethidine.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Fosamprenavir.
PimecrolimusThe metabolism of Pimecrolimus can be decreased when combined with Fosamprenavir.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Fosamprenavir.
PosaconazoleThe serum concentration of the active metabolites of Fosamprenavir can be increased when Fosamprenavir is used in combination with Posaconazole.
PropafenoneThe serum concentration of Propafenone can be increased when it is combined with Fosamprenavir.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Fosamprenavir.
RaltegravirThe serum concentration of Raltegravir can be decreased when it is combined with Fosamprenavir.
RanitidineThe serum concentration of Fosamprenavir can be decreased when it is combined with Ranitidine.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Fosamprenavir.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Fosamprenavir.
RifabutinThe serum concentration of the active metabolites of Rifabutin can be increased when Rifabutin is used in combination with Fosamprenavir.
RifampicinThe serum concentration of Fosamprenavir can be decreased when it is combined with Rifampicin.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Fosamprenavir.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Fosamprenavir.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Fosamprenavir.
SaquinavirThe serum concentration of Fosamprenavir can be increased when it is combined with Saquinavir.
SaxagliptinThe serum concentration of Saxagliptin can be increased when it is combined with Fosamprenavir.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Fosamprenavir.
SiltuximabThe serum concentration of Fosamprenavir can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Fosamprenavir.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Fosamprenavir.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Fosamprenavir.
St. John's WortThe metabolism of Fosamprenavir can be increased when combined with St. John's Wort.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Fosamprenavir.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Fosamprenavir.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Fosamprenavir.
TemsirolimusThe risk or severity of adverse effects can be increased when Fosamprenavir is combined with Temsirolimus.
TesmilifeneThe serum concentration of Fosamprenavir can be decreased when it is combined with Tesmilifene.
TipranavirThe serum concentration of Fosamprenavir can be decreased when it is combined with Tipranavir.
TocilizumabThe serum concentration of Fosamprenavir can be decreased when it is combined with Tocilizumab.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Fosamprenavir.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Fosamprenavir.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Fosamprenavir.
TrazodoneThe serum concentration of Trazodone can be increased when it is combined with Fosamprenavir.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Fosamprenavir.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Fosamprenavir.
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Fosamprenavir.
VerapamilThe serum concentration of Fosamprenavir can be increased when it is combined with Verapamil.
VilazodoneThe serum concentration of Vilazodone can be increased when it is combined with Fosamprenavir.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Fosamprenavir.
VindesineThe serum concentration of Vindesine can be increased when it is combined with Fosamprenavir.
VoriconazoleThe serum concentration of the active metabolites of Fosamprenavir can be increased when Fosamprenavir is used in combination with Voriconazole.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Fosamprenavir.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Fosamprenavir.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Fosamprenavir.
ZuclopenthixolThe serum concentration of Zuclopenthixol can be increased when it is combined with Fosamprenavir.
Food Interactions
  • Avoid alcohol, especially with the oral solution since it contains propylene glycol which competes with alcohol for alcohol dehydrogenase metabolism.
  • Take with or without food, however avoid lipid-rich meals.
  • Vitamin E increases fosamprenavir bioavailability.

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. Hoffman RM, Umeh OC, Garris C, Givens N, Currier JS: Evaluation of sex differences of fosamprenavir (with and without ritonavir) in HIV-infected men and women. HIV Clin Trials. 2007 Nov-Dec;8(6):371-80. [PubMed:18042502 ]
  2. Furfine ES, Baker CT, Hale MR, Reynolds DJ, Salisbury JA, Searle AD, Studenberg SD, Todd D, Tung RD, Spaltenstein A: Preclinical pharmacology and pharmacokinetics of GW433908, a water-soluble prodrug of the human immunodeficiency virus protease inhibitor amprenavir. Antimicrob Agents Chemother. 2004 Mar;48(3):791-8. [PubMed:14982766 ]
  3. Sension M: Initial therapy for human immunodeficiency virus: broadening the options. HIV Clin Trials. 2004 Mar-Apr;5(2):99-111. [PubMed:15116286 ]
  4. Wood R, Arasteh K, Stellbrink HJ, Teofilo E, Raffi F, Pollard RB, Eron J, Yeo J, Millard J, Wire MB, Naderer OJ: Six-week randomized controlled trial to compare the tolerabilities, pharmacokinetics, and antiviral activities of GW433908 and amprenavir in human immunodeficiency virus type 1-infected patients. Antimicrob Agents Chemother. 2004 Jan;48(1):116-23. [PubMed:14693528 ]
  5. Wire MB, Shelton MJ, Studenberg S: Fosamprenavir : clinical pharmacokinetics and drug interactions of the amprenavir prodrug. Clin Pharmacokinet. 2006;45(2):137-68. [PubMed:16485915 ]
  6. 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. Wire MB, Shelton MJ, Studenberg S: Fosamprenavir : clinical pharmacokinetics and drug interactions of the amprenavir prodrug. Clin Pharmacokinet. 2006;45(2):137-68. [PubMed:16485915 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 30, 2007 11:17 / Updated on July 25, 2016 03:10