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Ledipasvir (Molecule of the Month for May 2017)

Harvoni



Ledipasvir is a drug for the treatment of hepatitis C that was developed by Gilead Sciences. In February 10, 2014 Gilead filed for U.S. approval of a ledipasvir/sofosbuvir fixed-dose combination tablet for genotype 1 hepatitis C. The ledipasvir/sofosbuvir combination is a direct-acting antiviral agent that interferes with HCV replication and can be used to treat patients with genotypes 1a or 1b without PEG-interferon or ribavirin. Ledipasvir is an inhibitor of NS5A, a hepatitis C virus protein.

Ledipasvir inhibits an important viral phosphoprotein, NS5A, which is involved in viral replication, assembly, and secretion. Sofosbuvir, on the other hand, is metabolized to a uridine triphosphate mimic, which acts as a RNA chain terminator when incorporated into RNA by NS5B polymerase.

Similar to sofosbuvir, the cost of Harvoni has been a controversial topic. It costs $1,125 per pill in the US, translating to $63,000 for an 8-week treatment course, $94,500 for a 12-week treatment course, or $189,000 for a 24-week treatment course. Gilead justifies the cost by outweighing the benefit of curing hepatitis C over the cost of spending double on liver transplants or temporarily treating liver diseases. Gilead has provided a ledipasvir/sofosbuvir assistance program for eligible underserved or underinsured hepatitis C patients who cannot afford the costs of treatment.

Formal Chemical Name (IUPAC)
methyl ((S)-1-((1S,3S,4R)-3-(6-(9,9-difluoro-7-(2-((S)-5-((methoxycarbonyl)-L-valyl)-5-azaspiro[2.4]heptan-6-yl)-1H-imidazol-4-yl)-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-3-methyl-1-oxobutan-2-yl)carbamate

References

https://en.wikipedia.org/wiki/Ledipasvir

Picture of Ledipasvir 3D model

click on the picture of  Ledipasvir above to interact
with the 3D model of the
Ledipasvir structure
(this will open a new browser window)

Picture of Ledipasvir

C49H54F2N8O6



Update by Karl Harrison
(Molecule of the Month for May 2017 )

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