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Merck
CN

SML4077

Simeprevir

≥98% (HPLC)

Synonym(s):

(2R,3aR,10Z,11aS,12aR,14aR)-N-(cyclopropylsulfonyl)-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-tetradecahydro-2-[[7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-methyl-4,14-dioxo-cyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxamide, TMC 435, TMC-435, TMC435, TMC 435350, TMC-435350, TMC435350

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About This Item

Empirical Formula (Hill Notation):
C38H47N5O7S2
CAS Number:
923604-59-5
Molecular Weight:
749.94
MDL number:
MFCD25563225
NACRES:
NA.21
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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SMILES string

[S](=O)(=O)(NC(=O)[C@]32NC(=O)[C@H]4[C@@H](C[C@@H](C4)Oc5c6c(nc(c5)c7[s]cc(n7)C(C)C)c(c(cc6)OC)C)C(=O)N(CCCC\C=C/[C@@H]3C2)C)C1CC1

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,41,4

InChI key

JTZZSQYMACOLNN-VDWJNHBNSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (Warmed)

storage temp.

-10 to -25°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Orally active, potent and selective hepatitis C virus (HCV) NS3 protease inhibitor.

Simeprevir (TMC435; TMC435350) is an orally active, potent and selective hepatitis C virus (HCV) NS3/4A serine protease inhibitor (Ki = 0.5/0.4 nM using genotype 1a (H77)/1b (con1b) protease domain) that effectively blocks HCV replication (EC50/EC90 = 8/24 nM post 72h treatment using Huh7-Luc HCV genotype 1b replicon reporter cell line), while exhibiting no inhibitory potency against a panel of non-HCV DNA and RNA viruses even at concentrations >10 µM.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000400257
0000400256
0000388478
0000400257
0000400256

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Åsa Rosenquist et al.
Journal of medicinal chemistry, 57(5), 1673-1693 (2014-01-23)
Hepatitis C virus is a blood-borne infection and the leading cause of chronic liver disease (including cirrhosis and cancer) and liver transplantation. Since the identification of HCV in 1989, there has been an extensive effort to identify and improve treatment
Pierre Raboisson et al.
Bioorganic & medicinal chemistry letters, 18(17), 4853-4858 (2008-08-06)
SAR analysis performed with a limited set of cyclopentane-containing macrocycles led to the identification of N-[17-[2-(4-isopropylthiazole-2-yl)-7-methoxy-8-methylquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo [13.3.0.0(4,6)]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamide (TMC435350, 32c) as a potent inhibitor of HCV NS3/4A protease (K(i)=0.36nM) and viral replication (replicon EC(50)=7.8nM). TMC435350 also displayed low in vitro clearance
Tse-I Lin et al.
Antimicrobial agents and chemotherapy, 53(4), 1377-1385 (2009-01-28)
The hepatitis C virus (HCV) NS3/4A serine protease has been explored as a target for the inhibition of viral replication in preclinical models and in HCV-infected patients. TMC435350 is a highly specific and potent inhibitor of NS3/4A protease selected from

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