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Identification
NameSimeprevir
Accession NumberDB06290
TypeSmall Molecule
GroupsApproved
Description

Simeprevir is a hepatitis C virus (HCV) NS3/4A protease inhibitor indicated in patient’s with HCV genotype 1 for the treatment of chronic hepatitis as a combination therapy, which includes peginterferon alfa and ribavirin. It was approved by the FDA in November 2014 and is marketed under the brand name Olysio.

Structure
Thumb
Synonyms
TMC435
TMC435350
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Galexoscapsule150 mgoralJanssen Inc2013-11-25Not applicableCanada
Olysiocapsule150 mg/1oralJanssen Products LP2013-11-222016-04-05Us
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Simeprevir sodium
ThumbNot applicableDBSALT001485
Categories
UNII9WS5RD66HZ
CAS number923604-59-5
WeightAverage: 749.939
Monoisotopic: 749.291690263
Chemical FormulaC38H47N5O7S2
InChI KeyInChIKey=JTZZSQYMACOLNN-RCSAWCOCNA-N
InChI
InChI=1/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+/s2
IUPAC Name
(1R,4R,6R,7Z,15R)-N-(cyclopropanesulfonyl)-17-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.0⁴,⁶]octadec-7-ene-4-carboxamide
SMILES
[H][C@]12C[C@]1(NC(=O)[C@]1([H])CC(C[C@@]1([H])C(=O)N(C)CCCC\C=C/2)OC1=CC(=NC2=C(C)C(OC)=CC=C12)C1=NC(=CS1)C(C)C)C(=O)NS(=O)(=O)C1CC1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Macrolactam
  • Alpha-amino acid amide
  • Quinoline
  • Anisole
  • Alkyl aryl ether
  • 2,4-disubstituted 1,3-thiazole
  • Benzenoid
  • Pyridine
  • Cyclopropanecarboxylic acid or derivatives
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Thiazole
  • Tertiary carboxylic acid amide
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationSimeprevir is indicated in patient's with hepatitis C virus (HCV) genotype 1 for the treatment of chronic hepatitis as a combination therapy, which includes peginterferon alfa and ribavirin.
PharmacodynamicsSimeprevir is a protease inhibitor for HCV NS3/4A protease, which is required for replication of the virus.
Mechanism of actionSimeprevir functions as a direct-acting antiviral agent because it inhibits hepatitis C viral replication by binding to and inhibiting the protease, hepatitis C virus (HCV) NS3/4A.
Related Articles
AbsorptionAfter oral administration, simeprevir reaches its maximum plasma concentrations in 4-6 hours.
Volume of distribution

The volume of distribution for simeprevir has yet to be determined.

Protein bindingSimeprevir is >99.9% plasma protein bound with albumin being the main plasma protein.
Metabolism

Simeprevir is mainly metabolized by CYP3A enzymes.

Route of eliminationSimeprevir is mainly eliminated through biliary excretion (91%). Elimination through the urine is insignificant (1%).
Half lifeThe half-life of simeprevir is about 41 hours in HCV patients.
Clearance

The clearance of simeprevir has yet to be determined.

ToxicityIn patients receiving the combination therapy, the most common adverse reactions were nausea, pruritus, photosensitivity, and rash.
Affected organisms
  • Hepatitis C virus, RSV and other RNA/DNA viruses
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Capsuleoral150 mg
Capsuleoral150 mg/1
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7671032 No2005-05-192025-05-19Us
US8148399 No2009-09-052029-09-05Us
US8349869 No2006-07-282026-07-28Us
US8741926 No2006-07-282026-07-28Us
US8754106 No2006-07-282026-07-28Us
US9040562 No2006-07-282026-07-28Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00303 mg/mLALOGPS
logP4.69ALOGPS
logP4.56ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)1.62ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area156.89 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity206.95 m3·mol-1ChemAxon
Polarizability79.98 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Raboisson P, de Kock H, Rosenquist A, Nilsson M, Salvador-Oden L, Lin TI, Roue N, Ivanov V, Wahling H, Wickstrom K, Hamelink E, Edlund M, Vrang L, Vendeville S, Van de Vreken W, McGowan D, Tahri A, Hu L, Boutton C, Lenz O, Delouvroy F, Pille G, Surleraux D, Wigerinck P, Samuelsson B, Simmen K: Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350. Bioorg Med Chem Lett. 2008 Sep 1;18(17):4853-8. doi: 10.1016/j.bmcl.2008.07.088. Epub 2008 Jul 24.

General References
  1. Raboisson P, de Kock H, Rosenquist A, Nilsson M, Salvador-Oden L, Lin TI, Roue N, Ivanov V, Wahling H, Wickstrom K, Hamelink E, Edlund M, Vrang L, Vendeville S, Van de Vreken W, McGowan D, Tahri A, Hu L, Boutton C, Lenz O, Delouvroy F, Pille G, Surleraux D, Wigerinck P, Samuelsson B, Simmen K: Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350. Bioorg Med Chem Lett. 2008 Sep 1;18(17):4853-8. doi: 10.1016/j.bmcl.2008.07.088. Epub 2008 Jul 24. [PubMed:18678486 ]
External Links
ATC CodesJ05AE14
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (85.3 KB)
Interactions
Drug Interactions
Drug
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Simeprevir.
ado-trastuzumab emtansineThe serum concentration of ado-trastuzumab emtansine can be increased when it is combined with Simeprevir.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Simeprevir.
AlfentanilThe serum concentration of Alfentanil can be increased when it is combined with Simeprevir.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Simeprevir.
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Simeprevir.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Simeprevir.
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Simeprevir.
AmiodaroneThe serum concentration of Amiodarone can be increased when it is combined with Simeprevir.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Simeprevir.
AmlodipineThe serum concentration of Amlodipine can be increased when it is combined with Simeprevir.
AmoxapineThe serum concentration of Amoxapine can be increased when it is combined with Simeprevir.
AprepitantThe serum concentration of Simeprevir can be increased when it is combined with Aprepitant.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Simeprevir.
ArmodafinilThe serum concentration of Armodafinil can be increased when it is combined with Simeprevir.
AtazanavirThe serum concentration of Simeprevir can be increased when it is combined with Atazanavir.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Simeprevir.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Simeprevir.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Simeprevir.
BatimastatThe serum concentration of Simeprevir can be increased when it is combined with Batimastat.
BenzphetamineThe serum concentration of Benzphetamine can be increased when it is combined with Simeprevir.
BexaroteneThe serum concentration of Simeprevir can be decreased when it is combined with Bexarotene.
BisoprololThe serum concentration of Bisoprolol can be increased when it is combined with Simeprevir.
BoceprevirThe serum concentration of Simeprevir can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Simeprevir can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Simeprevir.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Simeprevir.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Simeprevir.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Simeprevir.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Simeprevir.
BuprenorphineThe serum concentration of Buprenorphine can be increased when it is combined with Simeprevir.
BuspironeThe serum concentration of Buspirone can be increased when it is combined with Simeprevir.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Simeprevir.
CabozantinibThe serum concentration of Cabozantinib can be increased when it is combined with Simeprevir.
CalcitriolThe serum concentration of Calcitriol can be increased when it is combined with Simeprevir.
CarbamazepineThe serum concentration of Simeprevir can be decreased when it is combined with Carbamazepine.
CeritinibThe serum concentration of Simeprevir can be increased when it is combined with Ceritinib.
ChlordiazepoxideThe serum concentration of Chlordiazepoxide can be increased when it is combined with Simeprevir.
ChloroquineThe serum concentration of Chloroquine can be increased when it is combined with Simeprevir.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Simeprevir.
CinacalcetThe serum concentration of Cinacalcet can be increased when it is combined with Simeprevir.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Simeprevir.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Simeprevir.
ClarithromycinThe serum concentration of Simeprevir can be increased when it is combined with Clarithromycin.
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Simeprevir.
ClonazepamThe serum concentration of Clonazepam can be increased when it is combined with Simeprevir.
ClorazepateThe serum concentration of Clorazepate can be increased when it is combined with Simeprevir.
CobicistatThe serum concentration of Simeprevir can be increased when it is combined with Cobicistat.
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Simeprevir.
CocaineThe serum concentration of Cocaine can be increased when it is combined with Simeprevir.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Simeprevir.
ConivaptanThe serum concentration of Simeprevir can be increased when it is combined with Conivaptan.
CrizotinibThe serum concentration of Simeprevir can be increased when it is combined with Crizotinib.
CyclophosphamideThe risk or severity of adverse effects can be increased when Simeprevir is combined with Cyclophosphamide.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Simeprevir.
Cyproterone acetateThe serum concentration of Cyproterone acetate can be increased when it is combined with Simeprevir.
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Simeprevir.
DabrafenibThe serum concentration of Simeprevir can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be increased when it is combined with Simeprevir.
DantroleneThe serum concentration of Dantrolene can be increased when it is combined with Simeprevir.
DapsoneThe serum concentration of Dapsone can be increased when it is combined with Simeprevir.
DarifenacinThe serum concentration of Darifenacin can be increased when it is combined with Simeprevir.
DarunavirThe serum concentration of Simeprevir can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Simeprevir.
DeferasiroxThe serum concentration of Simeprevir can be decreased when it is combined with Deferasirox.
DelavirdineThe serum concentration of Simeprevir can be increased when it is combined with Delavirdine.
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Simeprevir.
DesogestrelThe serum concentration of Desogestrel can be decreased when it is combined with Simeprevir.
DexamethasoneThe serum concentration of Simeprevir can be decreased when it is combined with Dexamethasone.
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Simeprevir.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Simeprevir.
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Simeprevir.
DiltiazemThe serum concentration of Simeprevir can be increased when it is combined with Diltiazem.
DisopyramideThe serum concentration of Disopyramide can be increased when it is combined with Simeprevir.
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Simeprevir.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Simeprevir.
DoxazosinThe serum concentration of Doxazosin can be increased when it is combined with Simeprevir.
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Simeprevir.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Simeprevir.
DronedaroneThe serum concentration of Simeprevir can be increased when it is combined with Dronedarone.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Simeprevir.
EfavirenzThe serum concentration of Simeprevir can be decreased when it is combined with Efavirenz.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Simeprevir.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Simeprevir.
EltrombopagThe serum concentration of Simeprevir can be increased when it is combined with Eltrombopag.
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Simeprevir.
EnzalutamideThe serum concentration of Simeprevir can be decreased when it is combined with Enzalutamide.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Simeprevir.
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Simeprevir.
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Simeprevir.
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Simeprevir.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Simeprevir.
ErythromycinThe serum concentration of Simeprevir can be increased when it is combined with Erythromycin.
EscitalopramThe serum concentration of Simeprevir can be decreased when it is combined with Escitalopram.
Eslicarbazepine acetateThe serum concentration of Simeprevir can be decreased when it is combined with Eslicarbazepine acetate.
EszopicloneThe serum concentration of Eszopiclone can be increased when it is combined with Simeprevir.
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Simeprevir.
EthosuximideThe serum concentration of Ethosuximide can be increased when it is combined with Simeprevir.
EthynodiolThe serum concentration of Ethynodiol can be decreased when it is combined with Simeprevir.
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Simeprevir.
EtravirineThe serum concentration of Simeprevir can be decreased when it is combined with Etravirine.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Simeprevir.
FelbamateThe serum concentration of Felbamate can be increased when it is combined with Simeprevir.
FelodipineThe serum concentration of Felodipine can be increased when it is combined with Simeprevir.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Simeprevir.
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Simeprevir.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Simeprevir.
FluconazoleThe serum concentration of Simeprevir can be increased when it is combined with Fluconazole.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Simeprevir.
FlurazepamThe serum concentration of Flurazepam can be increased when it is combined with Simeprevir.
FlutamideThe serum concentration of Flutamide can be increased when it is combined with Simeprevir.
FosamprenavirThe serum concentration of Simeprevir can be increased when it is combined with Fosamprenavir.
FosaprepitantThe serum concentration of Simeprevir can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of Simeprevir can be decreased when it is combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Simeprevir can be increased when it is combined with Fusidic Acid.
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Simeprevir.
GuanfacineThe serum concentration of Guanfacine can be increased when it is combined with Simeprevir.
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Simeprevir.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Simeprevir.
Hydroxyprogesterone caproateThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Simeprevir.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Simeprevir.
IdelalisibThe serum concentration of Simeprevir can be increased when it is combined with Idelalisib.
ImatinibThe serum concentration of Simeprevir can be increased when it is combined with Imatinib.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Simeprevir.
IndinavirThe serum concentration of Simeprevir can be increased when it is combined with Indinavir.
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Simeprevir.
IsavuconazoniumThe serum concentration of Simeprevir can be increased when it is combined with Isavuconazonium.
IsoflurophateThe serum concentration of Simeprevir can be increased when it is combined with Isoflurophate.
IsosorbideThe serum concentration of Isosorbide can be increased when it is combined with Simeprevir.
Isosorbide DinitrateThe serum concentration of Isosorbide Dinitrate can be increased when it is combined with Simeprevir.
Isosorbide MononitrateThe serum concentration of Isosorbide Mononitrate can be increased when it is combined with Simeprevir.
IsradipineThe serum concentration of Isradipine can be increased when it is combined with Simeprevir.
ItraconazoleThe serum concentration of Simeprevir can be increased when it is combined with Itraconazole.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Simeprevir.
IvacaftorThe serum concentration of Simeprevir can be increased when it is combined with Ivacaftor.
IxabepiloneThe serum concentration of Ixabepilone can be increased when it is combined with Simeprevir.
KetamineThe serum concentration of Ketamine can be increased when it is combined with Simeprevir.
KetoconazoleThe serum concentration of Simeprevir can be increased when it is combined with Ketoconazole.
LapatinibThe serum concentration of Lapatinib can be increased when it is combined with Simeprevir.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Simeprevir.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Simeprevir.
LidocaineThe serum concentration of Lidocaine can be increased when it is combined with Simeprevir.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Simeprevir.
LopinavirThe serum concentration of Lopinavir can be increased when it is combined with Simeprevir.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Simeprevir.
LuliconazoleThe serum concentration of Simeprevir can be increased when it is combined with Luliconazole.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Simeprevir.
MACITENTANThe serum concentration of MACITENTAN can be increased when it is combined with Simeprevir.
MaravirocThe serum concentration of Maraviroc can be increased when it is combined with Simeprevir.
MefloquineThe serum concentration of Mefloquine can be increased when it is combined with Simeprevir.
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Simeprevir.
MethadoneThe serum concentration of Methadone can be increased when it is combined with Simeprevir.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Simeprevir.
MifepristoneThe serum concentration of Simeprevir can be increased when it is combined with Mifepristone.
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Simeprevir.
MitotaneThe serum concentration of Simeprevir can be decreased when it is combined with Mitotane.
ModafinilThe serum concentration of Simeprevir can be decreased when it is combined with Modafinil.
NafcillinThe serum concentration of Simeprevir can be decreased when it is combined with Nafcillin.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Simeprevir.
NateglinideThe serum concentration of Nateglinide can be increased when it is combined with Simeprevir.
NefazodoneThe serum concentration of Simeprevir can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Simeprevir can be increased when it is combined with Nelfinavir.
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Simeprevir.
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Simeprevir.
NilotinibThe serum concentration of Simeprevir can be increased when it is combined with Nilotinib.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Simeprevir.
NisoldipineThe serum concentration of Nisoldipine can be increased when it is combined with Simeprevir.
NorethisteroneThe serum concentration of Norethindrone can be decreased when it is combined with Simeprevir.
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Simeprevir.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Simeprevir.
OxycodoneThe serum concentration of Oxycodone can be increased when it is combined with Simeprevir.
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Simeprevir.
PalbociclibThe serum concentration of Simeprevir can be increased when it is combined with Palbociclib.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Simeprevir.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Simeprevir.
PethidineThe risk or severity of adverse effects can be increased when Simeprevir is combined with Pethidine.
PhenobarbitalThe serum concentration of Simeprevir can be decreased when it is combined with Phenobarbital.
PhenytoinThe serum concentration of Simeprevir can be decreased when it is combined with Phenytoin.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Simeprevir.
PipotiazineThe serum concentration of Pipotiazine can be increased when it is combined with Simeprevir.
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Simeprevir.
PorfimerSimeprevir may increase the photosensitizing activities of Porfimer.
PosaconazoleThe serum concentration of Simeprevir can be increased when it is combined with Posaconazole.
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Simeprevir.
PraziquantelThe serum concentration of Praziquantel can be increased when it is combined with Simeprevir.
PrimidoneThe serum concentration of Simeprevir can be decreased when it is combined with Primidone.
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Simeprevir.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Simeprevir.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Simeprevir.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Simeprevir.
QuinineThe serum concentration of Quinine can be increased when it is combined with Simeprevir.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Simeprevir.
RegorafenibThe serum concentration of Regorafenib can be increased when it is combined with Simeprevir.
RifabutinThe serum concentration of Simeprevir can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Simeprevir can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Simeprevir can be decreased when it is combined with Rifapentine.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Simeprevir.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Simeprevir.
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Simeprevir.
RitonavirThe serum concentration of Simeprevir can be increased when it is combined with Ritonavir.
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Simeprevir.
RuxolitinibThe serum concentration of Ruxolitinib can be increased when it is combined with Simeprevir.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Simeprevir.
SaquinavirThe serum concentration of Simeprevir can be increased when it is combined with Saquinavir.
SaxagliptinThe serum concentration of Saxagliptin can be increased when it is combined with Simeprevir.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Simeprevir.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Simeprevir.
SiltuximabThe serum concentration of Simeprevir can be decreased when it is combined with Siltuximab.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Simeprevir.
SolifenacinThe serum concentration of Solifenacin can be increased when it is combined with Simeprevir.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Simeprevir.
SpiramycinThe serum concentration of Spiramycin can be increased when it is combined with Simeprevir.
St. John's WortThe serum concentration of Simeprevir can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Simeprevir can be increased when it is combined with Stiripentol.
SufentanilThe serum concentration of Sufentanil can be increased when it is combined with Simeprevir.
SunitinibThe serum concentration of Sunitinib can be increased when it is combined with Simeprevir.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Simeprevir.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Simeprevir.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Simeprevir.
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Simeprevir.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Simeprevir.
TelaprevirThe serum concentration of Simeprevir can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Simeprevir can be increased when it is combined with Telithromycin.
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Simeprevir.
TeniposideThe serum concentration of Teniposide can be increased when it is combined with Simeprevir.
TenofovirThe serum concentration of Simeprevir can be decreased when it is combined with Tenofovir.
TeriflunomideThe serum concentration of Simeprevir can be increased when it is combined with Teriflunomide.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Simeprevir.
TiagabineThe serum concentration of Tiagabine can be increased when it is combined with Simeprevir.
TipranavirThe serum concentration of Simeprevir can be increased when it is combined with Tipranavir.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Simeprevir.
TocilizumabThe serum concentration of Simeprevir can be decreased when it is combined with Tocilizumab.
TofacitinibThe serum concentration of Tofacitinib can be increased when it is combined with Simeprevir.
TolterodineThe serum concentration of Tolterodine can be increased when it is combined with Simeprevir.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Simeprevir.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Simeprevir.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Simeprevir.
TrazodoneThe serum concentration of Trazodone can be increased when it is combined with Simeprevir.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Simeprevir.
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Simeprevir.
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Simeprevir.
VardenafilThe serum concentration of Vardenafil can be increased when it is combined with Simeprevir.
VemurafenibThe serum concentration of Vemurafenib can be increased when it is combined with Simeprevir.
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Simeprevir.
VerapamilThe serum concentration of Simeprevir can be increased when it is combined with Verapamil.
VerteporfinSimeprevir may increase the photosensitizing activities of Verteporfin.
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Simeprevir.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Simeprevir.
VinorelbineThe serum concentration of Vinorelbine can be increased when it is combined with Simeprevir.
VoriconazoleThe serum concentration of Simeprevir can be increased when it is combined with Voriconazole.
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Simeprevir.
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Simeprevir.
ZonisamideThe serum concentration of Zonisamide can be increased when it is combined with Simeprevir.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Simeprevir.
Food Interactions
  • Simeprevir should be taken with food.

Targets

Kind
Protein
Organism
Hepatitis C virus
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type peptidase activity
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q91RS4
Molecular Weight:
19113.77 Da
References
  1. Raboisson P, de Kock H, Rosenquist A, Nilsson M, Salvador-Oden L, Lin TI, Roue N, Ivanov V, Wahling H, Wickstrom K, Hamelink E, Edlund M, Vrang L, Vendeville S, Van de Vreken W, McGowan D, Tahri A, Hu L, Boutton C, Lenz O, Delouvroy F, Pille G, Surleraux D, Wigerinck P, Samuelsson B, Simmen K: Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350. Bioorg Med Chem Lett. 2008 Sep 1;18(17):4853-8. doi: 10.1016/j.bmcl.2008.07.088. Epub 2008 Jul 24. [PubMed:18678486 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
no
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. FDA label.
  2. Lexicomp
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Lexicomp

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
Actions
binder
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. FDA label.

Transporters

Kind
Protein
Organism
Human
Pharmacological action
no
Actions
substrateinhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. FDA label.
  2. Lexicomp.
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
substrateinhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
References
  1. FDA label.
  2. Lexicomp.
Comments
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Drug created on March 19, 2008 10:22 / Updated on May 01, 2016 02:29