Sofosbuvir

April 30, 2018
I鈥檓 a hepatitis C drug that has been fought over in court.
What molecule am I?
Image of Sofosbuvir 3D Image of Sofosbuvir

Hepatitis C is a burgeoning disease that is still in search of a one-drug-fits-all solution. Currently, each hepatitis C virus genotype is treated with a pharmaceutical cocktail that consists of a mixture of antivirals, most of whose names end with 鈥渧ir鈥�.

Sofosbuvir is one such compound. It was discovered in 2007 by Michael Sofia at Pharmasset (now part of Gilead Sciences) and approved for use in the United States by the Food and Drug Administration in 2013. The FDA approval was for the combination of sofosbuvir and ribavirin, an antiviral that dates back to 1972. Sofosbuvir is the active ingredient in Gilead鈥檚 products Sovaldi and Harvoni, ads for which you may have seen on TV.

Sofosbuvir was the subject of a high-profile patent lawsuit involving Gilead and drug giant Merck. Merck contended that sofosbuvir was patterned after a patent awarded to Idenix Pharmaceuticals, a company that Merck had acquired. After a series of trials, a federal jury ordered Gilead to pay Merck US$2.54 billion (that鈥檚 right, billion) for infringing the Idenix patent.

Gilead appealed; and this past February, the judge in a US district court , writing that the Idenix patent was too broad and that a skilled chemist could not easily derive sofosbuvir from the information in the patent. For the same reason, the judge invalidated the patent.

Merck has vowed to appeal the overturn ruling.听

Sofosbuvir hazard information

GHS classification*: skin irritation, category 2听 听听
H315鈥擟auses skin irritation听
GHS classification: skin sensitization, category 1
H317鈥擬ay cause an allergic skin reaction
GHS classification: serious eye damage, category 1
H318鈥擟auses serious eye damage听Chemical Safety Warning
GHS classification: respiratory sensitisation, category 1
H334鈥擬ay cause allergy or asthma symptoms or breathing difficulties if inhaledChemical Safety Warning
GHS classification: specific target organ toxicity, single exposure, respiratory tract irritation, category3
H335鈥擬ay cause respiratory irritationChemical Safety Warning
GHS classification: germ cell mutagenicity, category 2
H341鈥擲uspected of causing genetic defectsChemical Safety Warning
GHS classification: reproductive toxicity, category 2
H361鈥擲uspected of damaging fertility or the unborn childChemical Safety Warning
GHS classification: specific target organ toxicity, single exposure, category 1
H370鈥擟auses damage to organs听Chemical Safety Warning
GHS classification: hazardous to the aquatic environment, long-term hazard, category 4
H413鈥擬ay cause long-lasting harmful effects to aquatic lifeChemical Safety Warning

*Globally Harmonized System of Classification and Labeling of Chemicals.听.

Sofosbuvir听fast facts

CAS Reg. No.1190307-88-0
Molar mass529.46 g/mol
Empirical formulaC22H29FN3O9P
AppearanceWhite to off-white crystals or powder
Melting point94鈥�125 潞C*
Water solubility鈮�105 mg/L*

*Depends on crystalline polymorph.

Chemical Abstract Service - a division of ACS

, the most authoritative and comprehensive source for chemical information.

Molecule of the Week needs your suggestions!

If your favorite molecule is not in our听archive, please send us a message. The molecule can be notable for its current or historical importance or for any quirky reason. Thank you!

Stay Ahead of the Chemistry Curve

Learn how ACS can help you stay ahead in the world of chemistry.