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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.
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.
Oseltamivir, sold under the brand name Tamiflu among others, is an antiviral medication used to treat and prevent influenza A and influenza B, viruses that cause the flu. [5] Many medical organizations recommend it in people who have complications or are at high risk of complications within 48 hours of first symptoms of infection. [ 6 ]
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 ...
[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]
Aminoshikimic acid is an intriguing alternative to shikimic acid as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir. [3] Aminoshikimic acid is also a versatile chiral starting material for the synthesis of new pharmaceuticals.
Dactylifric acid (also known as dattelic acid or 5-O-caffeoylshikimic acid [2] [3] [4]) is an ester derived from caffeic acid and shikimic acid. It and its isomers are enzymic browning substrates found in dates (Phoenix dactylifera fruits). [3] [5] Some older sources identify dactylifric acid as 3-O-caffeoylshikimic acid. [5]
For many biologics (e.g., monoclonal antibodies), injection site reactions are the most common adverse effect of the drug, and have been reported to have an incidence rate of 0.5–40%. [ 2 ] In trials of subcutaneous administration of oligonucleotides , between 22 and 100% of subjects developed reactions depending on the oligonucleotide.