Fosamprenavir

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Fosamprenavir
Systematic (IUPAC) name
[(2R,3S)-1-[(4-aminophenyl)sulfonyl-(2-methyl propyl)amino]-3-{[(3S)-oxolan-3-yl]oxycarbonylamino}- 4-phenyl-butan-2-yl]oxyphosphonic acid
Identifiers
CAS number	226700-81-8
ATC code	J05AE07
PubChem	131536
Chemical data
Formula	C25H36N3O9PS
Mol. mass	585.608 g/mol 623.700 g/mol (calcium salt)
Pharmacokinetic data
Bioavailability	Unknown
Protein binding	90%
Metabolism	Hydrolysed to amprenavir and phosphate in GI tract epithelium
Half life	7.7 hours
Excretion	Fecal (as metabolites of amprenavir)
Therapeutic considerations
Pregnancy cat.	C (U.S.)
Legal status	℞-only (U.S.), POM (UK)
Routes	Oral

Fosamprenavir (marketed by GlaxoSmithKline as fosamprenavir calcium, under the trade names Lexiva and Telzir) 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. Although fosamprenavir does not itself require refrigeration, it is usually given with ritonavir which does.

[edit] References

1. ^ Eron J Jr, Yeni P, Gathe J Jr, et al. (2006). "The KLEAN study of fosamprenavir-ritonavir versus lopinavir-ritonavir, each in combination with abacavir-lamivudine, for initial treatment of HIV infection over 48 weeks: a randomised non-inferiority trial". Lancet 368: 476–82. doi:10.1016/S0140-6736(06)69155-1. 

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