Asunaprevir

Identification

Summary

Asunaprevir is an NS3 protease inhibitor used to treat hepatitis C genotype 1b.

Generic Name
Asunaprevir
DrugBank Accession Number
DB11586
Background

Asunaprevir, also named BMS-650032, is a potent hepatitis C virus (HCV) NS3 protease inhibitor. It has been shown to have a very high efficacy in dual-combination regimens with daclatasvir in patients chronically infected with HCV genotype 1b.2 It was developed by Bristol-Myers Squibb Canada and approved by Health Canada on April 22, 2016. The commercialization of asunaprevir was cancelled one year later on October 16, 2017.4

Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Structure
Weight
Average: 748.286
Monoisotopic: 747.270476492
Chemical Formula
C35H46ClN5O9S
Synonyms
  • Asunaprevir
External IDs
  • BMS 650032
  • BMS-650032

Pharmacology

Indication

Asunaprevir is indicated in combination with other agents for the treatment of chronic hepatitis C in adult patients with hepatitis C virus genotypes 1 or 4 and compensated liver cirrhosis.5

Hepatitis C is a liver disease caused by the hepatitis C virus. The chronic state of this condition accounts for 60-80% of the cases from which the risk of cirrhosis of the liver within 20 years is of around 15-30%.6 The genotype 1 is the most common type of hepatitis C in the United States and the most difficult to treat.7

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatChronic hepatitis c genotype 1•••••••••••••••••
Used in combination to treatChronic hepatitis c genotype 4•••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Studies in vitro demonstrated a significant antiviral activity in HCV replicon cell systems with an EC50 of 4nm and 1nm against the HCV genotype 1a and 1b respectively.2 These studies showed a limited activity against the genotypes 2 and 3. This property makes asunaprevir a highly selective anti-HCV agent that is not effective against HCV closely related virus.3 Asunaprevir produce robust declines in HCV RNA levels in patients with HCV genotype 1 infection.1In clinical studies, it has been shown that asunaprevir is well-tolerated and the mean maximum HCV RNA level reduction from baseline was of approximately 2.87 log10 IU/ml.2

Monotherapy clinical studies with asunaprevir showed a mean maximum decline of HCV RNA in the range of 0.28-2.87 log10 IU/ml when administered in increasing doses from 10-600 mg. When asunaprevir was used as a combination product, it was possible to obtain a sustained virological response (aviremia 24 weeks after completion of therapy) in 83-92% of the patients.3

Mechanism of action

Asunaprevir is a highly active HCV NS3 protease inhibitor.1 The genome of HCV has a positive polarity which allows it to be translated into a protein in the host cell without further transformation steps. However, the resultant protein needs to be divided by the enzyme NS3 protease into single proteins in order to be able to exert its enzymatic activity or structural role. Therefore, due to NS3 vital importance for viral replication, the inhibiting action of asunaprevir causes a robust antiviral activity.3

TargetActionsOrganism
AGenome polyprotein
inhibitor
Hepatitis C virus genotype 1b (isolate BK)
Absorption

In preclinical studies, asunaprevir showed a high liver-to-plasma AUC ratio. It is rapidly absorbed within 30 minutes of administration.5 Clinical pharmacokinetic studies showed a Tmax of 2-4 hours.3 The pharmacokinetic profile act in a dose-proportional manner and in a dose of 100 mg the steady-state Cmax and AUC was 572 ng/ml and 1887 ng x h/mL. The absolute bioavailability is reported to be 9.3%. The absorption of asunaprevir is increased with food.8

Volume of distribution

The registered volume of distribution at steady state is 194 L.8

Protein binding

Protein binding of asunaprevir is very high and it can reach more than 99% of the administered dose independently of the dose. In vitro studies with human Caco-2 cells indicated that asunaprevir is a substrate of P-gp, OATP1B1 and OATP2B1.8

Metabolism

Asunaprevir is metabolized by the liver.3 The metabolism is mainly marked by oxidative reactions mediated by the activity of CYP3A.8 Asunaprevir seems to weakly induce its own metabolism and from the circulating dose, just about 5% of the administered dose is formed by metabolites.5 The metabolites of asunaprevir are formed after mono- and bis-oxidation, N-dealkylation, loss of isoquinoline ring and O-demethylation. All the metabolic reactions form about 15 metabolites and studies have reported that the main metabolic activity is performed by CYP3A4 and CYP3A5 with some minor activity from CYP2A6, CYP2B6, CYP2C9, CYP2C19 and CYP2D6.8

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Route of elimination

Asunaprevir is primarily eliminated via the feces.3 From the administered dose, 84% is excreted by feces mainly as metabolites and less than 1% of the dose is recovered as metabolites in the urine. The proportion of unchanged asunaprevir recovered in feces represents only 7.5% of the dose.8

Half-life

Clinical pharmacokinetic studies showed a mean terminal half-life of 15-20 hours.3

Clearance

Clinical pharmacokinetic studies showed a mean oral clearance of 302-491 L/h.3

Adverse Effects
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Toxicity

Toxicity studies showed no carcinogenic nor genotoxic potential related to asunaprevir. In the case of overdose, clinical studies reported no unexpected adverse events.8 Asunaprevir had no effects on fertility in preclinical studies. It has been shown that asunaprevir gets localized in the GI tract and liver and thus, increased hepatic transaminases were observed as well as changes in iron metabolism and decreased serum proteins. These effects are not progressive and asunaprevir was generally well tolerated.5

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
AbametapirThe serum concentration of Asunaprevir can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Asunaprevir can be increased when combined with Abatacept.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Asunaprevir.
AbirateroneThe metabolism of Asunaprevir can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Asunaprevir.
Food Interactions
  • Avoid St. John's Wort. This herb induces CYP3A metabolism and may reduce serum levels of asunaprevir. Co-administration of asunaprevir with St. John's Wort is contraindicated.
  • Exercise caution with grapefruit products. Grapefruit inhibits CYP3A metabolism, which may increase the serum concentration of asunaprevir.
  • Take with or without food.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SunvepraCapsule100 mgOralBristol Myers Squibb2016-04-222017-10-16Canada flag

Categories

ATC Codes
J05AP06 — AsunaprevirJ05AP58 — Daclatasvir, asunaprevir and beclabuvir
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Valine and derivatives / Proline and derivatives / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Isoquinolines and derivatives / Pyrrolidinecarboxamides / N-acylpyrrolidines / Alkyl aryl ethers / Pyridines and derivatives / Aryl chlorides
show 16 more
Substituents
Alkyl aryl ether / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Hepatitis C Virus

Chemical Identifiers

UNII
S9X0KRJ00S
CAS number
630420-16-5
InChI Key
XRWSZZJLZRKHHD-WVWIJVSJSA-N
InChI
InChI=1S/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1
IUPAC Name
tert-butyl N-[(2S)-1-[(2S,4R)-4-[(7-chloro-4-methoxyisoquinolin-1-yl)oxy]-2-{[(1R,2S)-1-[(cyclopropanesulfonyl)carbamoyl]-2-ethenylcyclopropyl]carbamoyl}pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
SMILES
COC1=CN=C(O[C@@H]2C[C@H](N(C2)C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C(=O)N[C@@]2(C[C@H]2C=C)C(=O)NS(=O)(=O)C2CC2)C2=C1C=CC(Cl)=C2

References

General References
  1. Lok AS, Gardiner DF, Lawitz E, Martorell C, Everson GT, Ghalib R, Reindollar R, Rustgi V, McPhee F, Wind-Rotolo M, Persson A, Zhu K, Dimitrova DI, Eley T, Guo T, Grasela DM, Pasquinelli C: Preliminary study of two antiviral agents for hepatitis C genotype 1. N Engl J Med. 2012 Jan 19;366(3):216-24. doi: 10.1056/NEJMoa1104430. [Article]
  2. McPhee F, Friborg J, Levine S, Chen C, Falk P, Yu F, Hernandez D, Lee MS, Chaniewski S, Sheaffer AK, Pasquinelli C: Resistance analysis of the hepatitis C virus NS3 protease inhibitor asunaprevir. Antimicrob Agents Chemother. 2012 Jul;56(7):3670-81. doi: 10.1128/AAC.00308-12. Epub 2012 Apr 16. [Article]
  3. Gentile I, Buonomo AR, Zappulo E, Minei G, Morisco F, Borrelli F, Coppola N, Borgia G: Asunaprevir, a protease inhibitor for the treatment of hepatitis C infection. Ther Clin Risk Manag. 2014 Jun 26;10:493-504. doi: 10.2147/TCRM.S66731. eCollection 2014. [Article]
  4. Health Canada [Link]
  5. Health Canada Approved Drug Products: Sunvepra (asunaprevir) capsule [Link]
  6. WHO [Link]
  7. HepatitisCentral [Link]
  8. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]
PubChem Compound
16076883
PubChem Substance
347827994
ChemSpider
17235944
BindingDB
50287594
RxNav
1652103
ChEBI
134723
ChEMBL
CHEMBL2105735
ZINC
ZINC000085540202
PharmGKB
PA166128168
PDBe Ligand
2R9
Wikipedia
Asunaprevir
PDB Entries
4nwl / 4wf8 / 4wh6 / 5eqs
MSDS
Download (23.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentHepatitis C Virus (HCV) Infection1
4Unknown StatusTreatmentChronic Hepatitis C Virus (HCV) Infection1
4WithdrawnTreatmentChronic Hepatitis C Virus (HCV) Infection1
3CompletedBasic ScienceChronic Hepatitis C Virus (HCV) Infection1
3CompletedTreatmentHepatitis C Virus (HCV) Infection7

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleNot applicable100 mg/1
CapsuleOral100 mg
Capsule, liquid filledOral100 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)145-155 ºC'MSDS
water solubility<50 mg/LAustralian Public Assessment
Predicted Properties
PropertyValueSource
Water Solubility0.00299 mg/mLALOGPS
logP3.12ALOGPS
logP3.37Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.77Chemaxon
pKa (Strongest Basic)1.85Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area182.33 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity186.82 m3·mol-1Chemaxon
Polarizability76.14 Å3Chemaxon
Number of Rings5Chemaxon
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/MSsplash10-0002-0002349100-69d3004995885cf73757
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f7p-4420639100-b2a014b58049c4909034
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-5320439000-ae0a319451ae80f11ec1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-2000590000-7d0bed9e05ec6063c59e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053u-4400295200-203693f61ad6c223de60
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000x-6311960100-e5890bd71f60c2df9f22
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-240.46361
predicted
DeepCCS 1.0 (2019)
[M+H]+242.18736
predicted
DeepCCS 1.0 (2019)
[M+Na]+248.51631
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Hepatitis C virus genotype 1b (isolate BK)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Core protein packages viral RNA to form a viral nucleocapsid, and promotes virion budding. Modulates viral translation initiation by interacting with HCV IRES and 40S ribosomal subunit. Also regula...
Gene Name
Not Available
Uniprot ID
P26663
Uniprot Name
Genome polyprotein
Molecular Weight
327190.435 Da
References
  1. Gentile I, Buonomo AR, Zappulo E, Minei G, Morisco F, Borrelli F, Coppola N, Borgia G: Asunaprevir, a protease inhibitor for the treatment of hepatitis C infection. Ther Clin Risk Manag. 2014 Jun 26;10:493-504. doi: 10.2147/TCRM.S66731. eCollection 2014. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
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. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
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
References
  1. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Eley T, Garimella T, Li W, Bertz RJ: Asunaprevir: A Review of Preclinical and Clinical Pharmacokinetics and Drug-Drug Interactions. Clin Pharmacokinet. 2015 Dec;54(12):1205-22. doi: 10.1007/s40262-015-0299-6. [Article]
  2. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
References
  1. Eley T, Han YH, Huang SP, He B, Li W, Bedford W, Stonier M, Gardiner D, Sims K, Rodrigues AD, Bertz RJ: Organic anion transporting polypeptide-mediated transport of, and inhibition by, asunaprevir, an inhibitor of hepatitis C virus NS3 protease. Clin Pharmacol Ther. 2015 Feb;97(2):159-66. doi: 10.1002/cpt.4. Epub 2014 Dec 20. [Article]
  2. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  3. Medicines.org: SUNVEPRA® asunaprevir PRODUCT INFORMATION [File]
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 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Eley T, Han YH, Huang SP, He B, Li W, Bedford W, Stonier M, Gardiner D, Sims K, Rodrigues AD, Bertz RJ: Organic anion transporting polypeptide-mediated transport of, and inhibition by, asunaprevir, an inhibitor of hepatitis C virus NS3 protease. Clin Pharmacol Ther. 2015 Feb;97(2):159-66. doi: 10.1002/cpt.4. Epub 2014 Dec 20. [Article]
  2. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
  3. Medicines.org: SUNVEPRA® asunaprevir PRODUCT INFORMATION [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
References
  1. Eley T, Han YH, Huang SP, He B, Li W, Bedford W, Stonier M, Gardiner D, Sims K, Rodrigues AD, Bertz RJ: Organic anion transporting polypeptide-mediated transport of, and inhibition by, asunaprevir, an inhibitor of hepatitis C virus NS3 protease. Clin Pharmacol Ther. 2015 Feb;97(2):159-66. doi: 10.1002/cpt.4. Epub 2014 Dec 20. [Article]
  2. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]
  3. Medicines.org: SUNVEPRA® asunaprevir PRODUCT INFORMATION [File]
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. Australian Therapeutic Goods Administration: Australian Public Assessment Report for asunaprevir [Link]

Drug created at April 27, 2016 23:10 / Updated at March 18, 2024 16:48