SIMEPREVIR

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National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H47N5O7S2
Molecular Weight	749.939
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of SIMEPREVIR

Structure Search

SMILES

[H][C@@]12C[C@H](C[C@@]1([H])C(=O)N(C)CCCCC=C[C@@H]3C[C@]3(NC2=O)C(=O)NS(=O)(=O)C4CC4)OC5=CC(=NC6=C5C=CC(OC)=C6C)C7=NC(=CS7)C(C)C

InChI

InChIKey=JTZZSQYMACOLNN-VDWJNHBNSA-N

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

HIDE SMILES / InChI

Molecular Formula	C38H47N5O7S2
Molecular Weight	749.939
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:22:44 UTC 2023` Edited by `admin` on `Fri Dec 15 18:22:44 UTC 2023`
Record UNII	9WS5RD66HZ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SIMEPREVIR

Official Name

English

TMC435

Common Name

English

TMC435350

Code

English

TMC 435350

Code

English

TMC 435

Code

English

SIMEPREVIR [VANDF]

Common Name

English

SIMEPREVIR [JAN]

Common Name

English

simeprevir [INN]

Common Name

English

SIMEPREVIR SODIUM [JAN]

Common Name

English

TMC-435

Code

English

Simeprevir [WHO-DD]

Common Name

English

SIMEPREVIR [USAN]

Common Name

English

SIMEPREVIR [MI]

Common Name

English

TMC-435350

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C783

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

WHO-ATC

J05AP05

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

WHO-ATC

J05AE14

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

NDF-RT

N0000182639

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

Code System Code Type Description

NDF-RT

N0000182638

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

HCV NS3/4A Protease Inhibitors [MoA]

FDA UNII

9WS5RD66HZ

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

NCI_THESAURUS

C129015

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

DRUG BANK

DB06290

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

WIKIPEDIA

Simeprevir

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

IUPHAR

7367

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

NDF-RT

N0000185503

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

P-Glycoprotein Inhibitors [MoA]

USAN

XX-54

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

DRUG CENTRAL

4812

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

PUBCHEM

24873435

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

ChEMBL

CHEMBL501849

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

NDF-RT

N0000182141

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

Cytochrome P450 3A4 Inhibitors [MoA]

CAS

1217263-04-1

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

NON-SPECIFIC STEREOCHEMISTRY

CAS

923604-59-5

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

NDF-RT

N0000190107

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]

INN

9432

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

LACTMED

Simeprevir

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

SMS_ID

100000134797

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

HSDB

8227

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

EVMPD

SUB64783

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

MERCK INDEX

m11694

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

EPA CompTox

DTXSID20919221

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

RXCUI

1482790

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

RxNorm

NDF-RT

N0000190108

Created by admin on Fri Dec 15 18:22:45 UTC 2023 , Edited by admin on Fri Dec 15 18:22:45 UTC 2023

PRIMARY

Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA]

Related Record Type Details


					9WS5RD66HZ

EXCRETED UNCHANGED

Comments:

Results from the mass balance trial demonstrated that the majority of the simeprevir dose is absorbed, with only 31.0% of dose excreted as unchanged drug in the feces (Trial C103).

Qualification:

FECAL

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> INHIBITOR

Interaction Type:

WEAK

Qualification:

IC50

Amount:


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> INHIBITOR

Comments:

Simeprevir inhibited P-gp-dependent transport of paclitaxel in Caco-2 cells with an IC50 value of 64.4 ug/mL (Study NC113).

Qualification:

IC50

Amount:


					S36X2B2WOX

HCV NS3-4A SERINE PROTEASE

TARGET -> INHIBITOR

Interaction Type:

INHIBITOR


					AIN96D6SGL

OATP1B1

TRANSPORTER -> SUBSTRATE


					16U7H60184

SIMEPREVIR SODIUM

SALT/SOLVATE -> PARENT


					66DDF797LP

OATP-8

TRANSPORTER -> SUBSTRATE


					G49RZO51ZC

OATP-B

TRANSPORTER -> SUBSTRATE


					AN4BU0U6DJ

HEPATITIS C VIRUS GENOTYPE 1

TARGET ORGANISM->INHIBITOR

Comments:

Specifically used for hepatitis C genotype 1 and 4.


					081I12ZA58

CYTOCHROME P450 2C19

METABOLIC ENZYME -> INHIBITOR

Interaction Type:

WEAK

Qualification:

IC50

Amount:


					L0423Z5LDW

CYTOCHROME P450 2C8

METABOLIC ENZYME -> SUBSTRATE


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Comments:

Plasma concentration will significantly increase if taken with medications that are strong CYP3A4 inhibitors (i.e. erythromycin, ritonavir) and will significantly decrease if taken with strong CYP3A4 inducers (i.e. efavirenz, rifampin, Saint John's wort).


					081I12ZA58

CYTOCHROME P450 2C19

METABOLIC ENZYME -> SUBSTRATE


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE


					L0423Z5LDW

CYTOCHROME P450 2C8

METABOLIC ENZYME -> INHIBITOR

Interaction Type:

CYP2C8

Qualification:

IC50

Amount:


					246D9TQ2XG

CYTOCHROME P450 2A6

METABOLIC ENZYME -> INHIBITOR

Interaction Type:

MODERATE

Qualification:

IC50

Amount:


					QI56415283

HEPATITIS C VIRUS

TARGET ORGANISM->INHIBITOR

Amount:


					8E4LAA4357

CYTOCHROME P450 2D6

METABOLIC ENZYME -> INHIBITOR

Interaction Type:

CYP2C8

Qualification:

IC50

Amount:

Related Record Type Details


					9WS5RD66HZ

ACTIVE MOIETY

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Tmax	PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC