Identification

Name
Elbasvir
Accession Number
DB11574
Type
Small Molecule
Groups
Approved
Description

Elbasvir is a direct acting antiviral medication used as part of combination therapy to treat chronic Hepatitis C, an infectious liver disease caused by infection with Hepatitis C Virus (HCV). HCV is a single-stranded RNA virus that is categorized into nine distinct genotypes, with genotype 1 being the most common in the United States, and affecting 72% of all chronic HCV patients [5]. Treatment options for chronic Hepatitis C have advanced significantly since 2011, with the development of Direct Acting Antivirals (DAAs) such as Elbasvir. Elbasvir is an inhibitor of NS5A, a protein essential for viral replication and virion assembly [Synthesis]. The barrier for develoment of resistance to NS5A inhibitors is lower than that of NS5B inhibitors, another class of DAAs [3]. Subtitutions at amino acid positions 28, 30, 31, or 93 are known to confer resistance to Elbasvir [FDA Label]. Despite this disadvantage Elbasvir is still effective against HCV particularly when paired with Grazoprevir.

In a joint recommendation published in 2016, the American Association for the Study of Liver Diseases (AASLD) and the Infectious Diseases Society of America (IDSA) recommend Elbasvir as first line therapy in combination with Grazoprevir for genotypes 1a, 1b, and 4 of Hepatitis C [3]. Elbasvir and Grazoprevir are used with or without Ribavirin with the intent to cure, or achieve a sustained virologic response (SVR), after 12 weeks of daily therapy. SVR and eradication of HCV infection is associated with significant long-term health benefits including reduced liver-related damage, improved quality of life, reduced incidence of Hepatocellular Carcinoma, and reduced all-cause mortality [4].

Elbasvir is available as a fixed dose combination product with Grazoprevir (tradename Zepatier) used for the treatment of chronic Hepatitis C. Approved in January 2016 by the FDA, Zepatier is indicated for the treatment of HCV genotypes 1 and 4 with or without Ribavirin depending on the the presence of resistance associated amino acid substitutions in the NS5A protein and previous treatment failure with Ribavirin, Peginterferon alfa-2a, Peginterferon alfa-2b, or other NS3/4A inhibitors like Boceprevir, Simeprevir, or Telaprevir [FDA Label]. When combined together, Elbasvir and Grazoprevir as the combination product Zepatier have been shown to achieve a SVR between 94% and 97% for genotype 1 and 97% and 100% for genotype 4 after 12 weeks of treatment [5]. It can be used in patients with compensated cirrhosis, human immunodeficiency virus co-infection, or severe kidney disease.

Structure
Thumb
Synonyms
Not Available
External IDs
MK 8742 / MK-8742 / MK8742
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ZepatierElbasvir (50 mg) + Grazoprevir (100 mg)Tablet, film coatedOralMerck Sharp & Dohme Limited2016-07-22Not applicableEu
ZepatierElbasvir (50 mg/1) + Grazoprevir (100 mg/1)Tablet, film coatedOralMerck Sharp & Dohme Limited2016-01-28Not applicableUs
ZepatierElbasvir (50 mg) + Grazoprevir (100 mg)TabletOralMerck Ltd.2016-01-25Not applicableCanada
Categories
UNII
632L571YDK
CAS number
1370468-36-2
Weight
Average: 882.035
Monoisotopic: 881.422445147
Chemical Formula
C49H55N9O7
InChI Key
BVAZQCUMNICBAQ-PZHYSIFUSA-N
InChI
InChI=1S/C49H55N9O7/c1-27(2)41(54-48(61)63-5)45(59)56-20-10-14-37(56)43-50-25-34(52-43)30-17-19-36-32(22-30)23-39-33-18-16-31(24-40(33)65-47(58(36)39)29-12-8-7-9-13-29)35-26-51-44(53-35)38-15-11-21-57(38)46(60)42(28(3)4)55-49(62)64-6/h7-9,12-13,16-19,22-28,37-38,41-42,47H,10-11,14-15,20-21H2,1-6H3,(H,50,52)(H,51,53)(H,54,61)(H,55,62)/t37-,38-,41-,42-,47-/m0/s1
IUPAC Name
methyl N-[(2S)-1-[(2S)-2-{4-[(9S)-5-{2-[(2S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-4-yl}-9-phenyl-8-oxa-10-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(17),2(7),3,5,11(16),12,14-heptaen-14-yl]-1H-imidazol-2-yl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
SMILES
COC(=O)N[[email protected]@H](C(C)C)C(=O)N1CCC[[email protected]]1C1=NC(=CN1)C1=CC2=C(C=C1)N1[[email protected]@H](OC3=C(C=CC(=C3)C3=CNC(=N3)[[email protected]@H]3CCCN3C(=O)[[email protected]@H](NC(=O)OC)C(C)C)C1=C2)C1=CC=CC=C1

Pharmacology

Indication

Elbasvir, when used in combination with Grazoprevir as the combination product Zepatier, is indicated for use with or without ribavirin for the treatment of chronic HCV genotypes 1 or 4 infection in adults [FDA Label].

Structured Indications
Pharmacodynamics

Elbasvir is classified as a direct-acting antiviral (DAA) and prevents viral replication in HCV genotypes 1a, 1b, and 4 [FDA Label].

Mechanism of action

Elbasvir is an inhibitor of the HCV non-structural protein 5A. While the precise role of this protein is unknown, it is essential to viral replication and virion assembly [Synthesis]. Potential modes of action of NS5A inhibitors like Elbasvir include blocking signaling interactions, redistribution of NS5A from the endoplasmic reticulum to the surface of lipid droplets, and modification of the HCV replication complex [3].

TargetActionsOrganism
ANonstructural Protein 5A (NS5A)
inhibitor
Hepatitis C Virus (HCV)
Absorption

Elbasvir reaches peak plasma concentration 3-6 hours after administration [FDA Label]. Elbasvir has an absolute bioavailability of 32%. When taken with food the peak concentration of Elbasvir increases 1.5 fold but this increase in exposure has not been deemed clinically relevant.

Volume of distribution

Elbasvir has an estimated apparent volume of distribution of 680 liters [FDA Label]. It is thought to distribute into most tissues including the liver.

Protein binding

Elbasvir is more than 99.9% bound to plasma proteins [FDA Label]. It binds both human serum albumin and α1-acid glycoprotein.

Metabolism

Elbasvir is partially eliminated by oxidative metabolism meditated by CYP3A [FDA Label]. No circulating metabolites of have been detected in human plasma.

Route of elimination

Elbasvir is mainly eliminated in the feces (90%) with very little eliminated in the urine (<1%) [FDA Label].

Half life

The geometric mean apparent terminal half-life for Grazoprevir is 24 hours in HCV-infected subjects [FDA Label].

Clearance

The clearance of Elbasvir has not been determined [FDA Label].

Toxicity

The most commonly reported adverse reactions of all intensity (greater than or equal to 5% in placebo-controlled trials) were fatigue, headache, and nausea [FDA Label].

Affected organisms
  • Hepatitis C Virus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AmiodaroneThe metabolism of Elbasvir can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Elbasvir can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Elbasvir can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Elbasvir can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Elbasvir is combined with Atorvastatin.Approved
BoceprevirThe metabolism of Elbasvir can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Elbasvir can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Elbasvir can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Elbasvir.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Elbasvir.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Elbasvir.Approved
CarbamazepineThe metabolism of Elbasvir can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Elbasvir can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Elbasvir.Withdrawn
ClarithromycinThe metabolism of Elbasvir can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Elbasvir can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Elbasvir can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Elbasvir can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Elbasvir can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Elbasvir can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Elbasvir can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Elbasvir can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Elbasvir can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Elbasvir can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Elbasvir can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Elbasvir can be decreased when combined with Delavirdine.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Elbasvir.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Elbasvir.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Elbasvir.Experimental
DihydroergotamineThe metabolism of Elbasvir can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Elbasvir can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Elbasvir can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Elbasvir can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Elbasvir can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Elbasvir.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Elbasvir.Approved
ErythromycinThe metabolism of Elbasvir can be decreased when combined with Erythromycin.Approved, Vet Approved
FluconazoleThe metabolism of Elbasvir can be decreased when combined with Fluconazole.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Elbasvir.Approved
FluvoxamineThe metabolism of Elbasvir can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Elbasvir can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Elbasvir can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Elbasvir can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Elbasvir can be increased when it is combined with Fusidic Acid.Approved
ImatinibThe metabolism of Elbasvir can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Elbasvir can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Elbasvir can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Elbasvir can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Elbasvir can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Elbasvir can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Elbasvir can be decreased when combined with Ketoconazole.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Elbasvir.Approved, Investigational
LopinavirThe metabolism of Elbasvir can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Elbasvir can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Elbasvir can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Elbasvir can be decreased when it is combined with Lumacaftor.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Elbasvir.Illicit, Investigational, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Elbasvir.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Elbasvir.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Elbasvir.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Elbasvir.Experimental
MifepristoneThe serum concentration of Elbasvir can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Elbasvir can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Elbasvir can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Elbasvir can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Elbasvir can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Elbasvir can be increased when combined with Nevirapine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Elbasvir.Approved, Investigational
NilotinibThe metabolism of Elbasvir can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Elbasvir can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Elbasvir can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Elbasvir can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Elbasvir can be increased when combined with Pentobarbital.Approved, Vet Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Elbasvir.Approved, Investigational, Vet Approved, Withdrawn
PhenobarbitalThe metabolism of Elbasvir can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Elbasvir can be increased when combined with Phenytoin.Approved, Vet Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Elbasvir.Approved
PosaconazoleThe metabolism of Elbasvir can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Elbasvir.Approved
PrimidoneThe metabolism of Elbasvir can be increased when combined with Primidone.Approved, Vet Approved
RanolazineThe serum concentration of Elbasvir can be increased when it is combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Elbasvir can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Elbasvir can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Elbasvir can be increased when combined with Rifapentine.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Elbasvir.Approved
SaquinavirThe metabolism of Elbasvir can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Elbasvir can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Elbasvir can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Elbasvir can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Elbasvir.Approved
St. John's WortThe serum concentration of Elbasvir can be decreased when it is combined with St. John&#39;s Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Elbasvir can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Elbasvir can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Elbasvir can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Elbasvir can be decreased when combined with Telithromycin.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Elbasvir.Experimental
TiclopidineThe metabolism of Elbasvir can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Elbasvir can be decreased when it is combined with Tocilizumab.Approved
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Elbasvir.Approved, Investigational, Nutraceutical
VenlafaxineThe metabolism of Elbasvir can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Elbasvir can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Elbasvir can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Elbasvir can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

Synthesis Reference

Coburn CA, Meinke PT, Chang W, Fandozzi CM, Graham DJ, Hu B, Huang Q, Kargman S, Kozlowski J, Liu R, McCauley JA, Nomeir AA, Soll RM, Vacca JP, Wang D, Wu H, Zhong B, Olsen DB, Ludmerer SW: Discovery of MK-8742: an HCV NS5A inhibitor with broad genotype activity. ChemMedChem. 2013 Dec;8(12):1930-40. doi: 10.1002/cmdc.201300343. Epub 2013 Oct 14.

General References
  1. Bell AM, Wagner JL, Barber KE, Stover KR: Elbasvir/Grazoprevir: A Review of the Latest Agent in the Fight against Hepatitis C. Int J Hepatol. 2016;2016:3852126. doi: 10.1155/2016/3852126. Epub 2016 Jun 15. [PubMed:27403342]
  2. Coburn CA, Meinke PT, Chang W, Fandozzi CM, Graham DJ, Hu B, Huang Q, Kargman S, Kozlowski J, Liu R, McCauley JA, Nomeir AA, Soll RM, Vacca JP, Wang D, Wu H, Zhong B, Olsen DB, Ludmerer SW: Discovery of MK-8742: an HCV NS5A inhibitor with broad genotype activity. ChemMedChem. 2013 Dec;8(12):1930-40. doi: 10.1002/cmdc.201300343. Epub 2013 Oct 14. [PubMed:24127258]
  3. Bagaglio S, Uberti-Foppa C, Morsica G: Resistance Mechanisms in Hepatitis C Virus: implications for Direct-Acting Antiviral Use. Drugs. 2017 May 12. doi: 10.1007/s40265-017-0753-x. [PubMed:28497432]
  4. Myers RP, Shah H, Burak KW, Cooper C, Feld JJ: An update on the management of chronic hepatitis C: 2015 Consensus guidelines from the Canadian Association for the Study of the Liver. Can J Gastroenterol Hepatol. 2015 Jan-Feb;29(1):19-34. Epub 2015 Jan 13. [PubMed:25585348]
  5. American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
External Links
KEGG Drug
D10625
PubChem Compound
71661251
PubChem Substance
347827988
ChemSpider
30843797
ChEBI
132967
ChEMBL
CHEMBL3039514
PharmGKB
PA166163436
RxList
RxList Drug Page
Wikipedia
Elbasvir
FDA label
Download (441 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentChronic Hepatitis C Infection / Transplant, Kidney1
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection / Impaired Renal Function1
1CompletedTreatmentHepatic Insufficiency1
1CompletedTreatmentHepatitis, Viral, Human1
1, 2RecruitingTreatmentEnd Stage Renal Disease (ESRD)1
1, 2RecruitingTreatmentHeart Failure, Unspecified1
2CompletedTreatmentChronic Hepatitis C Infection7
2CompletedTreatmentHepatitis C Virus (HCV)1
2RecruitingTreatmentAcute Hepatitis C / Human Immunodeficiency Virus (HIV)1
2, 3CompletedTreatmentChronic Hepatitis C Infection1
2, 3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2, 3CompletedTreatmentHepatitis C Virus (HCV)1
3CompletedTreatmentChronic Hepatitis C Infection2
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
3CompletedTreatmentHepatitis C Infection1
3Not Yet RecruitingTreatmentChronic HCV Infection1
3Not Yet RecruitingTreatmentChronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV)1
3Not Yet RecruitingTreatmentChronic Hepatitis C Infection / Compensated liver disease1
3Not Yet RecruitingTreatmentChronic hepatitis C genotype 1b / Cirrhoses, Liver / Fibrosis, Liver / Metabolic Syndromes1
3RecruitingTreatmentAcute Hepatitis C / Chronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV)1
3RecruitingTreatmentHepatitis C, Chronic1
3WithdrawnTreatmentChronic Hepatitis C Infection1
3WithdrawnTreatmentChronic Hepatitis C Infection / Transplantation, Liver1
4Active Not RecruitingTreatmentChronic Hepatitis C Infection / End-Stage Renal Disease (ESRD)1
4Enrolling by InvitationTreatmentChronic Hepatitis C Infection / Substance Abuse, Intravenous / Substance Use Disorder (SUD)1
4Not Yet RecruitingPreventionChronic Hepatitis C Infection / Renal Failure Chronic1
4Not Yet RecruitingTreatmentChronic Hepatitis C Infection2
4Not Yet RecruitingTreatmentTo Assess the Efficacy of Grazoprevir 100mg and Elbasvir 50mg by Determining the Proportion of Sustained Virological Response 12 Weeks After the End of Therapy1
4RecruitingPreventionRenal Failure1
4RecruitingTreatmentChronic Hepatitis C Infection1
4RecruitingTreatmentChronic Hepatitis C Infection / Disorder of Transplanted Kidney / Renal Insufficiency,Chronic1
4RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection2
4SuspendedPreventionCardiac Transplant Disorder / Chronic Hepatitis C Infection1
4WithdrawnTreatmentChronic Hepatitis C Infection1
4WithdrawnTreatmentHCV1
Not AvailableNot Yet RecruitingTreatmentHCV, HCC1
Not AvailableRecruitingNot AvailableChronic Hepatitis C Infection1
Not AvailableRecruitingNot AvailableHepatitis C, Chronic / Human Immunodeficiency Virus (HIV)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
Tablet, film coatedOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8871759No2011-05-042031-05-04Us
US7973040No2009-07-242029-07-24Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0044 mg/mLALOGPS
logP6.17ALOGPS
logP7.07ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)12.42ChemAxon
pKa (Strongest Basic)5.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area188.8 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity241.02 m3·mol-1ChemAxon
Polarizability98.71 Å3ChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Valine and derivatives
Alternative Parents
Alpha amino acid amides / Indoles / N-acylpyrrolidines / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Pyrroles / Heteroaromatic compounds / Imidazoles / Methylcarbamates / Organic carbonic acids and derivatives
show 7 more
Substituents
Valine or derivatives / Alpha-amino acid amide / Indole / Indole or derivatives / N-acylpyrrolidine / Monocyclic benzene moiety / Benzenoid / Methylcarbamate / Azole / Imidazole
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

1. Nonstructural Protein 5A (NS5A)
Kind
Protein
Organism
Hepatitis C Virus (HCV)
Pharmacological action
Yes
Actions
Inhibitor

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxygen binding
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxygen binding
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Monooxygenase activity
Specific Function
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name
CYP3A43
Uniprot ID
Q9HB55
Uniprot Name
Cytochrome P450 3A43
Molecular Weight
57669.21 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
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
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da

Drug created on April 07, 2016 10:37 / Updated on December 01, 2017 16:21