Simeprevir

Simeprevir
Clinical data
Pronunciation	/sɪˈmɛprəvɪər/; si-MEP-rə-veer
Trade names	Olysio, Sovriad, Galexos, others
Other names	TMC435; TMC435350
AHFS/Drugs.com	Monograph
MedlinePlus	a614013
License data	EU EMA: by INN; US DailyMed: Simeprevir;
Routes of; administration	By mouth
ATC code	J05AP05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	62% (under fed conditions)
Protein binding	>99.9%
Metabolism	Liver (CYP3A, CYP2C8, CYP2C19)
Elimination 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;
CAS Number	923604-59-5;
PubChem CID	24873435;
IUPHAR/BPS	7367;
DrugBank	DB06290;
ChemSpider	23331536;
UNII	9WS5RD66HZ;
KEGG	D10081;
ChEMBL	ChEMBL501849;
NIAID ChemDB	489101;
CompTox Dashboard (EPA)	DTXSID20919221 ;
ECHA InfoCard	100.215.933
Chemical and physical data
Formula	C38H47N5O7S2
Molar mass	749.94 g·mol−1
3D model (JSmol)
	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 brand name 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 developed by Medivir AB and Janssen Pharmaceutica. It was approved for medical use in the United States in 2013. It was removed from the World Health Organization's List of Essential Medicines in 2019. It is not available as a generic medication as of 2015.

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