Simeprevir

Simeprevir

Clinical data
Pronunciation	sim-E-pre-vir
Trade names	Olysio, Sovriad, Galexos, others
AHFS/Drugs.com	Monograph
MedlinePlus	a614013
Pregnancy category	US: C (Risk not ruled out) and X
Routes of administration	By mouth (capsules)
ATC code	J05AE14 (WHO)
Legal status
Legal status	US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	62% (under fed conditions)
Protein binding	>99.9%
Metabolism	Hepatic (CYP3A, CYP2C8, CYP2C19)
Biological half-life	10–13 hours (HCV-uninfected subjects), 41 hours (HCV-infected subjects)
Excretion	Feces (91%), urine (<1%)
Identifiers
IUPAC name (2R,3aR,10Z,11aS,12aR,14aR)-N-(Cyclopropylsulfonyl)-2-{[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy}-5-methyl-4,14-dioxo-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxamide
Synonyms	TMC435; TMC435350
CAS Number	923604-59-5
PubChem CID	56928193
IUPHAR/BPS	7367
DrugBank	DB06290
ChemSpider	23331536
UNII	9WS5RD66HZ
KEGG	D10081
ChEMBL	CHEMBL501849
NIAID ChemDB	489101
ECHA InfoCard	100.215.933
Chemical and physical data
Formula	C38H47N5O7S2
Molar mass	749.94 g/mol
3D model (Jmol)	Interactive image
SMILES Cc1c(ccc2c1nc(cc2O[C@@H]3C[C@@H]4[C@@H](C3)C(=O)N(CCCC/C=C\[C@@H]5C[C@]5(NC4=O)C(=O)NS(=O)(=O)C6CC6)C)c7nc(cs7)C(C)C)OC
InChI InChI=1S/C38H47N5O7S2/c1-21(2)30-20-51-35(40-30)29-18-32(26-13-14-31(49-5)22(3)33(26)39-29)50-24-16-27-28(17-24)36(45)43(4)15-9-7-6-8-10-23-19-38(23,41-34(27)44)37(46)42-52(47,48)25-11-12-25/h8,10,13-14,18,20-21,23-25,27-28H,6-7,9,11-12,15-17,19H2,1-5H3,(H,41,44)(H,42,46)/b10-8-/t23-,24-,27-,28-,38-/m1/s1 Key:JTZZSQYMACOLNN-VDWJNHBNSA-N

Simeprevir, sold under the trade names Olysio among others, is a medication used in combination with other medications for the treatment of hepatitis C. It is specifically used for hepatitis C genotype 1 and 4. Medications it is used with include sofosbuvir or ribavirin and peginterferon-alfa. Cure rates are in 80s to 90s percent. It may be used in those who also have HIV/AIDS. It is taken by mouth once daily for typically 12 weeks.

Common side effects include feeling tired, headache, rash, itchiness, and sensitivity to sunlight. In those with previous hepatitis B infection, active disease may recur. It is not recommended in those with significant liver problems. During pregnancy when used with ribavirin it may cause harm to the baby while when used with sofosbuvir its safety is unclear. Simeprevir is a HCV protease inhibitor.

Simeprevir was as developed by Medivir AB and Janssen Pharmaceutica. It was approved for medical use in the United States in 2013. Simeprevir is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is not available as a generic medication as of 2015. In the United Kingdom a course of treatment with ribavirin and peginterferon-alfa cost about 29,700 pounds in 2015. In the United States a course of treatment with sofosbuvir was more than 171,000 USD in 2015 with the simeprevir component costing 66,360 USD.

Simeprevir is indicated treating chronic hepatic C (CHC) infection as a part of a triple antiviral treatment regimen consisting of two other drugs: peginterferon-alfa (PEG-IFN) and ribavirin (RBV). It is primarily effective in treating Hepatitis C virus (HCV) genotype 1 infected subjects with compensated liver disease, including cirrhosis. There are currently no studies that show Simeprevir’s effectiveness as a single therapy for HCV. Simeprevir is generally used for HCV genotype 1 infected subjects, but off-label medical use has been indicated for type 4 genotype as well.