Telaprevir

Identification

Summary

Telaprevir is an NS3/4A viral protease inhibitor used in combination with other antivirals for the curative treatment of chronic Hepatitis C Virus infections.

Generic Name
Telaprevir
DrugBank Accession Number
DB05521
Background

Telaprevir 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 7. Treatment options for chronic Hepatitis C have advanced significantly since 2011, with the development of Direct Acting Antivirals (DAAs) such as Telaprevir. Telaprevir is an inhibitor of NS3/4A, a serine protease enzyme, encoded by HCV genotype 1 Label. These enzymes are essential for viral replication and serve to cleave the virally encoded polyprotein into mature proteins like NS4A, NS4B, NS5A and NS5B. The barrier for develoment of resistance to NS3/4A inhibitors is lower than that of NS5B inhibitors, another class of DAAs 6. Subtitutions at amino acid positions 155, 156, or 168 are known to confer resistance. The substitutions of the enzyme's catalytic triad consisting of H58, D82, and S139 are also likely to alter the affinity of the drug for NS3/4A or the activity of the enzyme itself. Despite this disadvantage Telaprevir is still effective against HCV when paired with Ribavirin, Peginterferon alfa-2a, and Peginterferon alfa-2b.

Telaprevir, Ribavirin, Peginterferon alfa-2a, and Peginterferon alfa-2b were used with the intent to cure, or achieve a sustained virologic response (SVR), after 12 weeks of daily administration of the combination therapy followed by 12 or 36 weeks of therapy with Ribavirin, Peginterferon alfa-2a, and Peginterferon alfa-2b. 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 5.

Telaprevir was available as a fixed dose product (tradename Incivek) used for the treatment of chronic Hepatitis C. Approved in May 2011 by the FDA, Incivek was indicated for the treatment of HCV genotype 1 in combination with Ribavirin, Peginterferon alfa-2a, and Peginterferon alfa-2b Label. Incivek has since been withdrawn from the market.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Weight
Average: 679.8493
Monoisotopic: 679.405732463
Chemical Formula
C36H53N7O6
Synonyms
  • (1S,3aR,6aS)-(2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydrocyclopenta(c)pyrrole-1-carboxamide
  • Telaprevir
External IDs
  • AIDS-213006
  • AIDS213006
  • LY 570310
  • LY-570310
  • MP 424
  • MP-424
  • VRT 111950
  • VRT-111950
  • VRT111950
  • VX 950
  • VX-950

Pharmacology

Indication

Telaprevir, when used in combination with Ribavirin, Peginterferon alfa-2a, and Peginterferon alfa-2b is indicated for use in the treatment of chronic HCV genotype 1 infection in adults Label.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatChronic hepatitis c genotype 1Regimen in combination with: Peginterferon alfa-2b (DB00022), Ribavirin (DB00811)•••••••••••••••••••••••
Used in combination to treatChronic hepatitis c genotype 1Regimen in combination with: Peginterferon alfa-2b (DB00022), Ribavirin (DB00811)•••••••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Telaprevir is classified as a direct-acting antiviral (DAA) and prevents viral replication in HCV genotype 1 Label.

Mechanism of action

Telaprevir is a NS3/4a protease inhibitor used to inhibit viral HCV replication Label. NS3/4a protease is an integral part of viral replication and mediates the cleavage the virally encoded polyprotein to mature proteins (NS4A, NS4B, NS5A and NS5B) Label. Telaprevir inhibits NS3/4A with an IC50 of 10nM.

TargetActionsOrganism
ANS3/4A protein
inhibitor
Hepatitis C Virus
USolute carrier organic anion transporter family member 1B1
inhibitor
Humans
USolute carrier organic anion transporter family member 2B1
inhibitor
Humans
Absorption

Telaprevir reaches peak plasma concentration 4-5hours after administration Label. Absolute bioavailability has not been determined. When taken with a normal fat meal (21g of fat), exposure increases by 235% compared to fasting conditions. With low (3.6g of fat) and high fat (56g of fat) meals, exposure increased 117% and 330% respectively.

Volume of distribution

The estimated apparent volume of distribution for Telapravir is 252 litres with an inter-individual variability of 72% Label.

Protein binding

Telapravir is 59-76% bound to human plasma proteins following a single dose Label. It binds to both human serum albumin and α1-acid glycoprotein.

Metabolism

Telaprevir is extensively metabolized via hydrolysis, oxidation, and reduction. The major metabolites of Telaprevir are pyrazinoic acid, a metabolite that underwent reduction at the α-ketoamide bond, and the R-diastereomer of telaprevir which is 30-fold less active than the parent compound were found to be the predominant metabolites. The primary enzyme involved in the metabolism of Telaprevir is CYP3A4. Some metabolism is performed by aldo-keto reductases and other reductases.

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Route of elimination

Telaprevir is mainly eliminated in the feces (82%) with a smaller amount eliminated via expiration (9%) and very little in the urine (1%) Label. 31.9% and 18.8% of drug in the feces was present as the parent compound and R-diastereomer of the parent compound respectively.

Half-life

Telaprevir has a half-life of elimination of 4.0-4.7 hours after a single dose and an effective half life of 9-11 hours at steady state Label.

Clearance

Telaprevir has an estimated aparent total body clearance of 32.4 liters per hour with an interindividual variability of 27.2% Label.

Adverse Effects
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Toxicity

Serious skin reactions, including Stevens Johnson Syndrome, Drug Reaction with Eosinophilia and Systemic Symptoms, and Toxic Epidermal Necrolysis, have been reported in patients treated with telaprevir combination treatment. Use of Ribavirin, Peginterferon alfa-2a, Peginterferon alfa-2b and Telaprevir is associated with a further increase in anemia frequency than in Ribavirin, Peginterferon alfa-2a, and Peginterferon alfa-2b without telaprevir.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be decreased when combined with Telaprevir.
AbametapirThe serum concentration of Telaprevir can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Telaprevir can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Telaprevir.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Telaprevir.
Food Interactions
  • Avoid St. John's Wort. St. John's Wort will decrease levels of this medication.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IncivekTablet, film coated375 mg/1OralVertex Pharmaceuticals Incorporated2011-05-232014-10-16US flag
IncivekTablet375 mgOralVertex Pharmaceuticals Incorporated2011-10-032015-04-21Canada flag
IncivoTablet, film coated375 mgOralJanssen Cilag International Nv2016-09-082016-10-06EU flag
IncivoTablet, film coated375 mgOralJanssen Cilag International Nv2016-09-082016-10-06EU flag

Categories

ATC Codes
J05AP02 — Telaprevir
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Hybrid peptides
Direct Parent
Hybrid peptides
Alternative Parents
Valine and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Pyrazinecarboxamides / 2-heteroaryl carboxamides / N-acylpyrrolidines / Pyrrolidinecarboxamides / N-acyl amines / Tertiary carboxylic acid amides / Heteroaromatic compounds
show 7 more
Substituents
2-heteroaryl carboxamide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Fatty acyl / Fatty amide
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oligopeptide, pyrazines, cyclopropanes, cyclopentapyrrole (CHEBI:68595)
Affected organisms
  • Hepatitis C Virus

Chemical Identifiers

UNII
655M5O3W0U
CAS number
402957-28-2
InChI Key
BBAWEDCPNXPBQM-GDEBMMAJSA-N
InChI
InChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25-,27-,28-,30+/m0/s1
IUPAC Name
(3S)-3-{[(1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-[(pyrazin-2-yl)formamido]acetamido]-3,3-dimethylbutanoyl]-octahydrocyclopenta[c]pyrrol-1-yl]formamido}-N-cyclopropyl-2-oxohexanamide
SMILES
[H][C@@]12CCC[C@]1([H])[C@H](N(C2)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)C1=NC=CN=C1)C1CCCCC1)C(C)(C)C)C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1

References

Synthesis Reference

Znabet A, Polak MM, Janssen E, de Kanter FJ, Turner NJ, Orru RV, Ruijter E. A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions. Chem Commun (Camb). 2010 Nov 14;46(42):7918-20. Epub 2010 Sep 20.

General References
  1. Kim JJ, Culley CM, Mohammad RA: Telaprevir: an oral protease inhibitor for hepatitis C virus infection. Am J Health Syst Pharm. 2012 Jan 1;69(1):19-33. doi: 10.2146/ajhp110123. [Article]
  2. Liu-Young G, Kozal MJ: Hepatitis C protease and polymerase inhibitors in development. AIDS Patient Care STDS. 2008 Jun;22(6):449-57. doi: 10.1089/apc.2007.0199. [Article]
  3. Forestier N, Zeuzem S: Telaprevir for the treatment of hepatitis C. Expert Opin Pharmacother. 2012 Mar;13(4):593-606. doi: 10.1517/14656566.2012.660524. Epub 2012 Feb 15. [Article]
  4. Garg V, Kauffman RS, Beaumont M, van Heeswijk RP: Telaprevir: pharmacokinetics and drug interactions. Antivir Ther. 2012;17(7):1211-21. doi: 10.3851/IMP2356. Epub 2012 Sep 7. [Article]
  5. 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. [Article]
  6. 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. [Article]
  7. American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
  8. FDA Approved Drug Products: Incivek (telaprevir) oral tablets [Link]
Human Metabolome Database
HMDB0015616
KEGG Drug
D09012
PubChem Compound
3010818
PubChem Substance
175427024
ChemSpider
2279948
BindingDB
50326056
RxNav
1102261
ChEBI
68595
ChEMBL
CHEMBL231813
ZINC
ZINC000003992480
PharmGKB
PA165958354
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Telaprevir
FDA label
Download (508 KB)
MSDS
Download (88.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
4CompletedTreatmentHepatitis C Virus (HCV) Infection1
4TerminatedTreatmentHepatitis C Virus (HCV) Infection2
4WithdrawnPreventionHepatitis C Virus (HCV) Infection1
4WithdrawnTreatmentHepatitis C Virus (HCV) Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral375 mg
Tablet, film coatedOral375 mg/1
Tablet, film coatedOral
Tablet, film coatedOral375 mg
Tablet, coatedOral375 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8431615No2013-04-302028-05-30US flag
US8529882No2013-09-102021-08-31US flag
US7820671No2010-10-262025-02-25US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility0.0047 mg/mLFDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.0355 mg/mLALOGPS
logP2.56ALOGPS
logP2.58Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)11.86Chemaxon
pKa (Strongest Basic)-0.58Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area179.56 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity180.04 m3·mol-1Chemaxon
Polarizability73.79 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9547
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7982
P-glycoprotein substrateSubstrate0.8567
P-glycoprotein inhibitor IInhibitor0.9355
P-glycoprotein inhibitor IIInhibitor0.8879
Renal organic cation transporterNon-inhibitor0.8919
CYP450 2C9 substrateNon-substrate0.8245
CYP450 2D6 substrateNon-substrate0.6612
CYP450 3A4 substrateSubstrate0.7632
CYP450 1A2 substrateNon-inhibitor0.6961
CYP450 2C9 inhibitorInhibitor0.5969
CYP450 2D6 inhibitorNon-inhibitor0.7431
CYP450 2C19 inhibitorInhibitor0.5866
CYP450 3A4 inhibitorInhibitor0.8926
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8476
Ames testNon AMES toxic0.7536
CarcinogenicityNon-carcinogens0.8622
BiodegradationNot ready biodegradable0.9954
Rat acute toxicity2.6980 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9894
hERG inhibition (predictor II)Inhibitor0.6931
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0159-9223442000-e5383967958c67d6112b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001s-0401934000-e689fea8fde6ccaa4da9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0096-3410197000-13f108f46b4afbc760f4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-015j-5563953000-154faaa74adaefc6bc61
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ir0-5941211000-9bfdc06611c63be57320
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052p-9741720000-7098774c3602e3863297
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pbc-9701231000-2e87aa7ba0cbdd1beefa
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-263.3125041
predicted
DarkChem Lite v0.1.0
[M-H]-255.8990041
predicted
DarkChem Lite v0.1.0
[M-H]-247.4829
predicted
DeepCCS 1.0 (2019)
[M+H]+261.7451041
predicted
DarkChem Lite v0.1.0
[M+H]+255.6741041
predicted
DarkChem Lite v0.1.0
[M+H]+249.69911
predicted
DeepCCS 1.0 (2019)
[M+Na]+263.2733041
predicted
DarkChem Lite v0.1.0
[M+Na]+254.9812041
predicted
DarkChem Lite v0.1.0
[M+Na]+255.84802
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Hepatitis C Virus
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type peptidase activity
Specific Function
Not Available
Gene Name
NS3/4A
Uniprot ID
B0B3C9
Uniprot Name
Genome polyprotein
Molecular Weight
72789.28 Da
References
  1. Liu-Young G, Kozal MJ: Hepatitis C protease and polymerase inhibitors in development. AIDS Patient Care STDS. 2008 Jun;22(6):449-57. doi: 10.1089/apc.2007.0199. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da

Enzymes

Kind
Protein
Organism
Humans
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
References
  1. Kim JJ, Culley CM, Mohammad RA: Telaprevir: an oral protease inhibitor for hepatitis C virus infection. Am J Health Syst Pharm. 2012 Jan 1;69(1):19-33. doi: 10.2146/ajhp110123. [Article]
  2. Kiang TK, Wilby KJ, Ensom MH: Telaprevir: clinical pharmacokinetics, pharmacodynamics, and drug-drug interactions. Clin Pharmacokinet. 2013 Jul;52(7):487-510. doi: 10.1007/s40262-013-0053-x. [Article]
  3. Rangnekar AS, Fontana RJ: Managing drug-drug interactions with boceprevir and telaprevir. Clin Liver Dis (Hoboken). 2012 Apr 26;1(2):36-40. doi: 10.1002/cld.10. eCollection 2012 Apr. [Article]
  4. Flockhart Table of Drug Interactions [Link]
  5. Telaprevir FDA label [File]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Garg V, Kauffman RS, Beaumont M, van Heeswijk RP: Telaprevir: pharmacokinetics and drug interactions. Antivir Ther. 2012;17(7):1211-21. doi: 10.3851/IMP2356. Epub 2012 Sep 7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Garg V, Kauffman RS, Beaumont M, van Heeswijk RP: Telaprevir: pharmacokinetics and drug interactions. Antivir Ther. 2012;17(7):1211-21. doi: 10.3851/IMP2356. Epub 2012 Sep 7. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
References
  1. Kiang TK, Wilby KJ, Ensom MH: Telaprevir: clinical pharmacokinetics, pharmacodynamics, and drug-drug interactions. Clin Pharmacokinet. 2013 Jul;52(7):487-510. doi: 10.1007/s40262-013-0053-x. [Article]
  2. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]

Drug created at November 18, 2007 18:25 / Updated at February 21, 2021 18:51