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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01319
rdf:type
n3:Drug
n3:description
Fosamprenavir is a prodrug of amprenavir, an inhibitor of human immunodeficiency virus (HIV) protease.
n3:dosage
n5:271B64B2-363D-11E5-9242-09173F13E4C5 n5:271B64B3-363D-11E5-9242-09173F13E4C5 n5:271B64B4-363D-11E5-9242-09173F13E4C5 n5:271B64B5-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# 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. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18373851 # 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":http://www.ncbi.nlm.nih.gov/pubmed/18042502 # 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":http://www.ncbi.nlm.nih.gov/pubmed/15341507 # 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":http://www.ncbi.nlm.nih.gov/pubmed/14982766 # Sension M: Initial therapy for human immunodeficiency virus: broadening the options. HIV Clin Trials. 2004 Mar-Apr;5(2):99-111. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15116286 # 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":http://www.ncbi.nlm.nih.gov/pubmed/14693528 # 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":http://www.ncbi.nlm.nih.gov/pubmed/12162471 # Wire MB, Shelton MJ, Studenberg S: Fosamprenavir : clinical pharmacokinetics and drug interactions of the amprenavir prodrug. Clin Pharmacokinet. 2006;45(2):137-68. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16485915
n3:group
approved
n3:halfLife
The plasma elimination half-life of amprenavir (the active metabolite) is approximately 7.7 hours.
n3:indication
Indicated 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.
owl:sameAs
n17:DB01319 n20:DB01319
dcterms:title
Fosamprenavir
adms:identifier
n7:DB01319 n9:116245 n10:131536 n13:46504901 n14:0173-0721-00 n15:PA10084 n24:Fosamprenavir
n3:mechanismOfAction
Fosamprenavir 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.
n3:packager
n21:271B64B0-363D-11E5-9242-09173F13E4C5 n21:271B64AE-363D-11E5-9242-09173F13E4C5 n21:271B64AF-363D-11E5-9242-09173F13E4C5 n21:271B64AC-363D-11E5-9242-09173F13E4C5 n21:271B64AD-363D-11E5-9242-09173F13E4C5 n21:271B64AB-363D-11E5-9242-09173F13E4C5
n3:patent
n8:6436989 n8:2224738 n8:2231700 n8:6514953
n3:routeOfElimination
Excretion 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.
n3:synonym
Fosamprenavir
n11:hasAHFSCode
n12:08-18-08-08
n3:foodInteraction
Vitamin E increases fosamprenavir bioavailability. 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.
n3:proteinBinding
Very high (approximately 90%); primarily bound to alpha 1 -acid glycoprotein. Higher amounts of unbound amprenavir present as amprenavir serum concentrations increase.
n3:synthesisReference
"DrugSyn.org":http://www.drugsyn.org/Fosamprenavir.htm
foaf:page
n19:fosamprenavir.html n23:lexiva.htm
n3:IUPAC-Name
n4:271B64BA-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B64C0-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B64BF-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B64BC-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B64BD-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B64BE-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B64B8-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B64B6-363D-11E5-9242-09173F13E4C5 n4:271B64B9-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B64B7-363D-11E5-9242-09173F13E4C5
n11:hasATCCode
n25:J05AE07
n3:H-Bond-Acceptor-Count
n4:271B64C6-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B64C7-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B64C1-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B64C2-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B64C4-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B64C3-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B64C5-363D-11E5-9242-09173F13E4C5
n3:absorption
The 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 C<sub>max</sub> of amprenavir after administration of the suspension formulation was 14.5 % higher compared with the tablet.
n3:affectedOrganism
Human Immunodeficiency Virus
n3:casRegistryNumber
226700-79-4
n3:category
n3:containedIn
n26:271B64B1-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B64CC-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B64CE-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B64CF-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B64CB-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B64CA-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B64CD-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B64BB-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B64C8-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B64C9-363D-11E5-9242-09173F13E4C5