Amprenavir

Molecular formula C25H35N3O6S Molecular weight 505.64 CAS Registry No 161814-49-9 Merck Index 13,594 

Sample preparation Condition a CIS SPE cartridge (Baker) with 3 mL MeOH and 3 mL water. Do not allow to run dry. Add 1 mL plasma to the SPE cartridge, wash with 2 mL water, suck dry for 1 min, elute with 2.6 mL MeOH. Evaporate a 1 mL ahquot of the eluate to dr5mess under a stream of nitrogen at 40°, reconstitute the residue with 200 xL mobile phase, inject a 100 pL ahquot. 

Mobile phase MeCN 40 mM disodium hydrogen phosphate containing 4% octanesul-fonic acid 50 50. (At the end of each session, wash column with MeOHiwater 50 50 and MeCN water S0 20.) 

Aymard, G. Legrand, M. Trichereau, N. Diquet, B. Determination of twelve antiretroviral agents in human plasma sample using reversed-phase high-performance liquid chromatography, J.Chromatogr. B, 2000, 744, 227-240. 

Sample preparation Mix 250 tL plasma with 50 p,L MeOH, add 100 p,L 2 p,gfmL IS in MeOH, add 250 p,L 1 M NaOH, add 3 mL hexaneiethyl acetate 50 50, shake at high speed for 25 min, centrifuge at 3000 g for 15 min. Evaporate the organic layer to dryness under a stream of air, reconstitute the residue with 1 mL initial mobile phase, inject a 20 xL aliquot. 

---

The Henry reactions of A, ALdibenzyl-L-phenylalaninal with nitroalkanes using 1.2 equiv of tetrabutylammonium fluoride (TBAF) as the catalyst proceed in ahighly stereoselective manner, as shown in Eqs. 3.82 and 3.83. This reaction provides rapid and stereoselective access to important molecules containing 1,3-diamino-2-hydroxypropyl segments, which are cenhal structural subunit of the HIV protease inhibitor amprenavir (in Scheme 3.21). 

Amprenavir (APV, Agenerase) is the most recently approved HIV protease inhibitor. It is smaller and stereochemically less complex than the other drugs in this class. Adsorption of this compound was found to be impaired by high fat meals. Common side effects of Amprenavir are nausea, vomiting, diarrhea, rash and a tingling sensation around the mouth. 

C9H13NO 104-63-2) see Indeloxacine Phenmetrazine 7-(2-benzylaminoethyl)theophylline (C15H19N5O2 22680-61-1) see Fenetylline Theodrenaline benzyl [(2R,35)-3-amino-2-hydroxy-4-phenylbutyl](2-methylpropyl)carbamate monohydrochloride (C22H3[C1N20j 160232-11-1) see Amprenavir 2-benzylamino-l-(4-methoxyphenyl)propane (C17H21NO 43229-65-8) see Fenoterol Formoterol benzyl [3-[(2-aminophenyl)carbamoyl]propyl]methyl> carbamate... 

C27H3 N20(, 160232-12-2) see Amprenavir (3S)-l-benzyl-3-hydroxypyrrolidine (CiiHijNO 101385-90-4) see Baraidipine... 

CjjHjjNjOgS 191226-98-9) see Amprenavir Ar-(crt-butyI-2-[2(t )-hydroxy-4-phenyl-3(S)-phthalimido-butyI]decahydro-(4a5,8aS)-isoquinoline-3(S)-carbox-amide... 

C4H5NO3 6066-82-6) see Amprenavir Aspoxicillin Cefotiam Imidapril Nateglinide Ritonavir Romurtide Spirapril... 

C25H33N3OSS 160231-69-6) see Amprenavir (35)-tetrabydro-3-furanyl [(15)-l-(25)-oxiranyl-2-pbenyl-etbyl]carbamate... 

Ci5Hi(,N04 160232-70-2) see Amprenavir [5-(iJ 4 )]-tetrabydro-3-furanyl [l-(pbenylmetbyl)-2-propenyl]carbamate... 

Lalezari JP, DeJesus E, Northfelt DW, Richmond G, Wolfe P, Haubrich R, Henry D, Powderly W, Becker S, Thompson M, Valentine E, Wright D, Carlson M, Riddler S, Haas FF, DeMasi R, Sista PR, Salgo M, Delehanty J (2003a) A controlled Phase II trial assessing three doses of enfuvirtide (T-20) in combination with abacavir, amprenavir, ritonavir and efavirenz in nonnucleoside reverse transcriptase inhibitor-naive HIV-infected adults. Antivir Ther 8 279-287... 

Changes in human immunodeficiency vims type 1 Gag at positions 1449 and P453 are linked to I50V protease mutants in vivo and cause reduction of sensitivity to amprenavir and improved viral fitness in vitro. J Virol 76 7398-7406... 

Polli JW, Jarrett JL, Studenberg SD, Humphreys JE, Dennis SW, Brouwer KR, et al. Role of P-glycoprotein on the CNS disposition of amprenavir (141W94), an HIV protease inhibitor. Pharm Res 1999 16 1206-12. 

Acetazolamide, amprenavir, captopril, hydralazine, hydrochlorothiazide, methyldopa, procainamide, quinidine, ticlopidine, and triamterene... 

Protease inhibitors (amprenavir, Increase or decrease serum levels of estrogen Decrease efficacy of COCs or increase... 

---