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The current production method is based on the first scalable synthesis developed by Gilead Sciences [4] starting from naturally occurring quinic acid or shikimic acid.Due to lower yields and the extra steps required (because of the additional dehydration), the quinic acid route was dropped in favour of the one based on shikimic acid, which received further improvements by Hoffmann-La Roche.
Oseltamivir was discovered by scientists at Gilead Sciences using shikimic acid as a starting point for synthesis; shikimic acid was originally available only as an extract of Chinese star anise; but by 2006, 30% of the supply was manufactured recombinantly in E. coli. [65] [66] Gilead exclusively licensed their relevant patents to Roche in ...
Shikimic acid can also be extracted from the seeds of the sweetgum (Liquidambar styraciflua) fruit, [2] which is abundant in North America, in yields of around 1.5%. For example, 4 kg (8.8 lb) of sweetgum seeds is needed for fourteen packages of Tamiflu. By comparison, star anise has been reported to yield 3% to 7% shikimic acid.
It was originally synthesised from shikimic acid extracted from the star anise plant. Oseltamivir is a prodrug that requires metabolism in the liver to the active form, oseltamivir carboxylate. This binds at the active site of the neuraminidase enzyme , preventing it from cleaving sialic acid to release the virus particle from the host cell.
EPSP synthase catalyzes the reaction which converts shikimate-3-phosphate plus phosphoenolpyruvate to 5-enolpyruvylshikimate-3-phosphate (EPSP) by way of an acetal-like tetrahedral intermediate. [ 9 ] [ 10 ] Basic and acidic amino acids in the active site are involved in deprotonation of the hydroxyl group of PEP and in the proton-exchange ...
pimobendan – phosphodiesterase 3 inhibitor used to manage heart failure in dogs; pirlimycin – antimicrobial; ponazuril – anticoccidial; praziquantel – treatment of infestations of the tapeworms Dipylidium caninum, Taenia pisiformis, Echinococcus granulosus; prazosin – sympatholytic used in hypertension and abnormal muscle contractions
[10] [11] [12] An industrial method for the production of shikimic acid using fermentation of E. coli bacteria was discovered in 2005, [13] [14] and applied in the 2009 swine flu pandemic to address Tamiflu shortages, eventually reversing price increases for star anise as a raw material of shikimic acid. [15]
Equine drug testing is a form of drug testing applied to performance horses in regulated competition. Most common in racehorses, drug tests are also performed on horses in endurance riding and in international competition such as the Olympics and FEI-sanctioned competition.
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