amprenavir amprenavir amprenavir (original brand name agenerase, glaxosmithkline) is a protease inhibitor used to treat hiv infection. it was approved by the food and drug administration on april 15, 1999, for twice-a-day dosing instead of needing to be taken every eight hours. the convenient dosing came at a price, as the dose required is 1,200 mg, delivered in 8 (eight) very large 150 mg gel capsules or 24 (twenty-four) 50 mg gel capsules twice daily. amprenavirclinical datatrade namesageneraseahfs/drugs.commonographmedlineplusa699051license data eu ema: by inn us fda: amprenavir routes ofadministrationoral (capsules)atc codej05ae05 (who) legal statuslegal status in general: ℞ (prescription only) pharmacokinetic dataprotein binding90%metabolismhepaticelimination half-life7.1–10.6 hoursexcretion<3% renalidentifiers iupac name (3s)-oxolan-3-yl n--1-phenylbutan-2-yl]carbamate cas number161814-49-9 ypubchem cid65016drugbankdb00701 ychemspider58532 yunii5s0w860xnrkeggd00894 ychebichebi:40050 ychemblchembl116 yniaid chemdb006080comptox dashboard (epa)dtxsid5046061 echa infocard100.262.589 chemical and physical dataformulac25h35n3o6smolar mass505.63 g·mol−13d model (jsmol)interactive image smiles o=c(o1ccoc1)n(cc2ccccc2)(o)cn(cc(c)c)s(=o)(=o)c3ccc(n)cc3 inchi inchi=1s/c25h35n3o6s/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29h,12-17,26h2,1-2h3,(h,27,30)/t21-,23-,24+/m0/s1 ykey:ymarzqaqmvyckc-oemfjlhtsa-n y (verify) it was patented in 1992 and approved for medical use in 1999. production of amprenavir was discontinued by the manufacturer on december 31, 2004; a prodrug version (fosamprenavir), is available. background hiv-1 protease dimer with amprenavir (sticks) bound in the active site. pdb entry 3nu3 research aimed at development of renin inhibitors as potential antihypertensive agents had led to the discovery of compounds that blocked the action of this peptide cleaving enzyme. the amino acid sequence cleaved by renin was found to be fortuitously the same as that required to produce the hiv peptide coat. structure–activity studies on renin inhibitors proved to be of great value for developing hiv protease inhibitors. incorporation of an amino alcohol moiety proved crucial to inhibitory activity for many of these agents. this unit is closely related to the one found in the statine, an unusual amino acid that forms part of the pepstatin, a fermentation product that inhibits protease enzymes.