Fosamprenavir
File:Fosamprenavir structure.svg | |
File:Fosamprenavir ball-and-stick.png | |
Systematic (IUPAC) name | |
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{[(2R,3S)-1-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid
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Clinical data | |
Trade names | Lexiva |
AHFS/Drugs.com | monograph |
MedlinePlus | a604012 |
Pregnancy category |
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Legal status |
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Routes of administration |
Oral |
Pharmacokinetic data | |
Bioavailability | Unknown |
Protein binding | 90% |
Metabolism | Hydrolysed to amprenavir and phosphate in GI tract epithelium |
Biological half-life | 7.7 hours |
Excretion | Fecal (as metabolites of amprenavir) |
Identifiers | |
CAS Number | 226700-81-8 |
ATC code | J05AE07 (WHO) |
PubChem | CID: 131536 |
DrugBank | DB01319 |
ChemSpider | 116245 |
UNII | WOU1621EEG |
ChEMBL | CHEMBL1664 |
NIAID ChemDB | 082186 |
Chemical data | |
Formula | C25H36N3O9PS |
Molecular mass | 585.608 g/mol 623.700 g/mol (calcium salt) |
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Fosamprenavir (marketed by ViiV Healthcare as the calcium salt), under the trade names Lexiva (U.S.) and Telzir (Europe) is a pro-drug of the protease inhibitor and antiretroviral drug amprenavir. The FDA approved it October 20, 2003, while the EMEA approved it on July 12, 2004. The human body metabolizes fosamprenavir in order to form 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.
A head-to-head study with lopinavir[1] showed the two drugs to have comparable potency, but patients on fosamprenavir tended to have a higher serum cholesterol. Fosamprenavir's main advantage over lopinavir is that it is cheaper.
References
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