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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H46N5O7S2.Na
Molecular Weight 771.921
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SIMEPREVIR SODIUM

SMILES

[Na+].COC1=CC=C2C(O[C@@H]3C[C@@H]4[C@@H](C3)C(=O)N(C)CCCCC=C[C@@H]5C[C@]5(NC4=O)C(=O)[N-]S(=O)(=O)C6CC6)=CC(=NC2=C1C)C7=NC(=CS7)C(C)C

InChI

InChIKey=LLXQGDWGCCKOQP-MVZLLIIPSA-M
InChI=1S/C38H47N5O7S2.Na/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,(H2,41,42,44,46);/q;+1/p-1/b10-8-;/t23-,24-,27-,28-,38-;/m1./s1

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C38H46N5O7S2
Molecular Weight 748.931
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Simeprevir is a hepatitis C virus (HCV) NS3/4A protease inhibitor approved for the treatment of Chronic Hepatitis C (genotype 1 and 4). Inhibiting NS3/4A, simeprevir blocks viral replication. In in vitro assays simeprevir was potent against HCV genotype 1a and 1b. Simeprevir must not be administered as monotherapy and should only be prescribed with both peginterferon alfa and ribavirin.

CNS Activity

CNS Penetrant
2588
Curator's Comment: There was minimal penetration of the blood-brain barrier.

Originator

Tibotec
10
Curator's Comment: Patent application WO2008092954A2 is a formulation patent, originally filed by Tibotec Pharmaceuticals, now part of Janssen Pharmaceuticals. The application claims a crystalline form of a substituted macro cyclic compound, preferably a variant of simeprevir, useful for the treatment of HCV infections.

Approval Year

2013
589
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.36 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
OLYSIO

Approved Use

Indicated for the treatment of chronic hepatitis C (CHC) genotype 1 or 4 infection as a component of a combination antiviral treatment regimen. OLYSIO monotherapy is not recommended.

Launch Date

2013
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2304 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
6172 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4067 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
11470 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
24630 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
79710 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
56430 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
206000 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16.04 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
41.32 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19852962/
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SIMEPREVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
unhealthy, 18–70 years
Health Status: unhealthy
Age Group: 18–70 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
Other AEs: Headache, Diarrhoea...
Other AEs:
Headache (13.5%)
Diarrhoea (10.8%)
Fatigue (10.8%)
Pruritus (10.8%)
Anorexia (8.1%)
Back pain (8.1%)
Myalgia (8.1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
400 mg 1 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
healthy, 24.0 years(range: 20-44 years)
Health Status: healthy
Age Group: 24.0 years(range: 20-44 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
healthy, 38.0 years (range: 23-55 years)
Health Status: healthy
Age Group: 38.0 years (range: 23-55 years)
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
200 mg 2 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
healthy, 38.0 years (range: 25-54 years)
Health Status: healthy
Age Group: 38.0 years (range: 25-54 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
Other AEs: Photosensitivity reaction, Diarrhea...
Other AEs:
Photosensitivity reaction (3 patients)
Diarrhea (2 patients)
Abdominal pain upper (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Disc. AE: Pruritus, Psoriasis...
AEs leading to
discontinuation/dose reduction:
Pruritus (<1%)
Psoriasis (<1%)
Rash (1%)
Rash erythematous (<1%)
Skin burning sensation (<1%)
Aggression (<1%)
Blood bilirubin increased (<1%)
Major depression (<1%)
Stomatitis (<1%)
Headache (<1%)
Pain (<1%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
AEs

AEs

AESignificanceDosePopulation
Diarrhoea 10.8%
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
unhealthy, 18–70 years
Health Status: unhealthy
Age Group: 18–70 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
Fatigue 10.8%
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
unhealthy, 18–70 years
Health Status: unhealthy
Age Group: 18–70 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
Pruritus 10.8%
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
unhealthy, 18–70 years
Health Status: unhealthy
Age Group: 18–70 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
Headache 13.5%
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
unhealthy, 18–70 years
Health Status: unhealthy
Age Group: 18–70 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
Anorexia 8.1%
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
unhealthy, 18–70 years
Health Status: unhealthy
Age Group: 18–70 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
Back pain 8.1%
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
unhealthy, 18–70 years
Health Status: unhealthy
Age Group: 18–70 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
Myalgia 8.1%
200 mg 1 times / day multiple, oral
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
unhealthy, 18–70 years
Health Status: unhealthy
Age Group: 18–70 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22326470
Abdominal pain upper 2 patients
200 mg 2 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
healthy, 38.0 years (range: 25-54 years)
Health Status: healthy
Age Group: 38.0 years (range: 25-54 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
Diarrhea 2 patients
200 mg 2 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
healthy, 38.0 years (range: 25-54 years)
Health Status: healthy
Age Group: 38.0 years (range: 25-54 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
Photosensitivity reaction 3 patients
200 mg 2 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
healthy, 38.0 years (range: 25-54 years)
Health Status: healthy
Age Group: 38.0 years (range: 25-54 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19852962
Rash 1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Aggression <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Blood bilirubin increased <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Headache <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Major depression <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Pain <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Pruritus <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Psoriasis <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Rash erythematous <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Skin burning sensation <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Stomatitis <1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
unhealthy, 49 years (range: 18-73 years)
Health Status: unhealthy
Age Group: 49 years (range: 18-73 years)
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/205123Orig1s000MedR.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inducer
1087
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2A6
879

CYP2C8
1057

CYP2C19
2057

CYP3A
227

OATP1B1
1079

NTCP
39

P-gp
1741

MRP2
499

BSEP
550

CYP1A
70

CYP2E1
1060
CYP2C8
810

CYP2C19
1119

P-gp
2052

MRP2
252

BCRP
697

OATP1B1/3
11

OATP2B1
122
CYP1A2
832
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
2546
 moderate [IC50 42.9 uM]
CYP2C8
1117
 moderate [IC50 49.1 uM]
CYP2A6
911
 moderate [IC50 59.7 uM]
CYP1A
122
 no
CYP1A2
2333
 no
CYP2C9
2497
 no
CYP2E1
1146
 no
CYP3A4
2633
 no
CYP3A
317
 weak [IC50 131 uM]
likely (co-administration study)
Comment: Concomitant use of OLYSIO with these antiarrhythmics may result in mild increases in concentrations of these antiarrhythmics due to intestinal CYP3A4 inhibition by simeprevir
Page: 37.0
CYP2C19
2141
 weak [IC50 86.1 uM]
BSEP
554
 yes [IC50 1.67 uM]
OATP1B1
1095
 yes [IC50 25 uM]
yes (co-administration study)
Comment: Concomitant use of OLYSIO with rosuvastatin resulted in increased plasma concentrations of rosuvastatin due to inhibition of OATP1B1 by simeprevir
Page: 38.0
NTCP
40
 yes [IC50 3.47 uM]
MRP2
625
 yes [IC50 6.4 uM]
P-gp
1932
 yes [IC50 85.9 uM]
yes (co-administration study)
Comment: Concomitant use of OLYSIO with digoxin resulted in increased concentrations of digoxin due to inhibition of P-gp by simeprevir
Page: 38.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
697
 yes
CYP2C19
1119
 yes
CYP2C8
810
 yes
MRP2
252
 yes
OATP1B1/3
11
 yes
OATP2B1
122
 yes
P-gp
2052
 yes
CYP3A4
1946
 yes
likely (co-administration study)
Comment: Concomitant use of OLYSIO with carbamazepine, oxcarbazepine, phenobarbital or phenytoin may result in significantly decreased plasma concentrations of simeprevir due to strong CYP3A induction by these anticonvulsants; Concomitant use of OLYSIO with clarithromycin or telithromycin may result in increased plasma concentrations of simeprevir due to CYP3A inhibition by these antibiotics
Page: 37.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
AChemBlock
R16014
AK Scientific
4041AH
AstaTech
33532
Chem Scene
CS-0338
eMolecules
313130810
Hangzhou APIChem Technology
AC-27651
Innovapharm
VT-00687829
KeyOrganics
AS-56205
Lan Pharmatech
LQT-B48548
mcule
MCULE-6850465396
mcule
MCULE-7634361057
MedChem Express
HY-10241
MolPort
MolPort-039-139-798
MolPort
MolPort-046-416-844
MolPort
MolPort-046-795-603
MuseChem
I009489
TargetMol
T4686
ZINC
ZINC000253632968
http://zinc15.docking.org/substances/ZINC000253632968
PubMed

PubMed

TitleDatePubMed
Improved P2 phenylglycine-based hepatitis C virus NS3 protease inhibitors with alkenylic prime-side substituents.
2010 Jul 15
Discovery of novel urea-based hepatitis C protease inhibitors with high potency against protease-inhibitor-resistant mutants.
2012 Apr 12
Synthesis and antiviral activity of novel HCV NS3 protease inhibitors with P4 capping groups.
2012 Dec 15
Highly efficient infectious cell culture of three hepatitis C virus genotype 2b strains and sensitivity to lead protease, nonstructural protein 5A, and polymerase inhibitors.
2014 Feb
Cost-effectiveness of sofosbuvir-based treatments for chronic hepatitis C in the US.
2015 Aug 5
Hepatitis C virus: Virology, diagnosis and treatment.
2015 Jun 8
Patents

Patents

20090281140
2
CN104473941A
2

Sample Use Guides

In Vivo Use Guide
The recommended dose is one 150 mg capsule taken once daily with food. OLYSIO should be administered with both peginterferon alfa and ribavirin. The recommended treatment duration of OLYSIO with peginterferon alfa and ribavirin is 12 weeks, followed by either 12 or 36 additional weeks of peginterferon alfa and ribavirin depending on prior response status.
Route of Administration: Oral
In Vitro Use Guide
The median simeprevir EC50 and EC90 values against a HCV genotype 1b replicon were 9.4 nM (7.05 ng/mL) and 19 nM (14.25 ng/mL), respectively.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:42:15 GMT 2025
Edited
by admin
on Mon Mar 31 22:42:15 GMT 2025
Record UNII
16U7H60184
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SIMEPREVIR SODIUM
WHO-DD  
Common Name English
OLYSIO
Preferred Name English
TMC-435 SODIUM SALT
Code English
Simeprevir sodium [WHO-DD]
Common Name English
SIMEPREVIR SODIUM [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS OLYSIO (AUTHORIZED: HEPATITS C, CHRONIC)
Created by admin on Mon Mar 31 22:42:15 GMT 2025 , Edited by admin on Mon Mar 31 22:42:15 GMT 2025
Code System Code Type Description
PUBCHEM
46866715
Created by admin on Mon Mar 31 22:42:15 GMT 2025 , Edited by admin on Mon Mar 31 22:42:15 GMT 2025
PRIMARY
EVMPD
SUB169848
Created by admin on Mon Mar 31 22:42:15 GMT 2025 , Edited by admin on Mon Mar 31 22:42:15 GMT 2025
PRIMARY
FDA UNII
16U7H60184
Created by admin on Mon Mar 31 22:42:15 GMT 2025 , Edited by admin on Mon Mar 31 22:42:15 GMT 2025
PRIMARY
DRUG BANK
DBSALT001485
Created by admin on Mon Mar 31 22:42:15 GMT 2025 , Edited by admin on Mon Mar 31 22:42:15 GMT 2025
PRIMARY
SMS_ID
100000159513
Created by admin on Mon Mar 31 22:42:15 GMT 2025 , Edited by admin on Mon Mar 31 22:42:15 GMT 2025
PRIMARY
RXCUI
1484518
Created by admin on Mon Mar 31 22:42:15 GMT 2025 , Edited by admin on Mon Mar 31 22:42:15 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL501849
Created by admin on Mon Mar 31 22:42:15 GMT 2025 , Edited by admin on Mon Mar 31 22:42:15 GMT 2025
PRIMARY
CAS
1241946-89-3
Created by admin on Mon Mar 31 22:42:15 GMT 2025 , Edited by admin on Mon Mar 31 22:42:15 GMT 2025
NON-SPECIFIC STOICHIOMETRY
Related Record Type Details
Structure of SIMEPREVIR
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of SIMEPREVIR
ACTIVE MOIETY
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