This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
Danoprevir
Accession Number
DB11779  (DB06038)
Type
Small Molecule
Groups
Investigational
Description

Danoprevir has been used in trials studying the treatment of Hepatitis C, Chronic.

Structure
Thumb
Synonyms
Not Available
External IDs
R-05190591 / R05190591 / RO-5190591 / RO5190591
Product Ingredients
IngredientUNIICASInChI Key
Danoprevir sodium217RJI972K916826-48-7GXYYUDQAGCVAGJ-HHGSPMIASA-M
Categories
UNII
911Z9PCQ5F
CAS number
850876-88-9
Weight
Average: 731.84
Monoisotopic: 731.300027418
Chemical Formula
C35H46FN5O9S
InChI Key
ZVTDLPBHTSMEJZ-JSZLBQEHSA-N
InChI
InChI=1S/C35H46FN5O9S/c1-34(2,3)50-32(45)37-27-13-8-6-4-5-7-11-22-17-35(22,31(44)39-51(47,48)24-14-15-24)38-29(42)28-16-23(19-41(28)30(27)43)49-33(46)40-18-21-10-9-12-26(36)25(21)20-40/h7,9-12,22-24,27-28H,4-6,8,13-20H2,1-3H3,(H,37,45)(H,38,42)(H,39,44)/b11-7-/t22-,23-,27+,28+,35-/m1/s1
IUPAC Name
(1S,4R,6S,7Z,14S,18R)-14-{[(tert-butoxy)carbonyl]amino}-4-[(cyclopropanesulfonyl)carbamoyl]-2,15-dioxo-3,16-diazatricyclo[14.3.0.0^{4,6}]nonadec-7-en-18-yl 4-fluoro-2,3-dihydro-1H-isoindole-2-carboxylate
SMILES
CC(C)(C)OC(=O)N[C@H]1CCCCC\C=C/[C@@H]2C[C@]2(NC(=O)[C@@H]2C[C@H](CN2C1=O)OC(=O)N1CC2=CC=CC(F)=C2C1)C(=O)NS(=O)(=O)C1CC1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action

Danoprevir is a NS3/4A protease inhibitor. The HCV NS3/4A protease is an attractive drug target because of its potential involvement in viral replication and suppressive effects on host response to viral infection. Inhibitors of the HCV protease, such as Danoprevir, represent a promising new class of drugs for HCV.

TargetActionsOrganism
UGenome polyproteinNot Available
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

Learn more
Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

Learn more
Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

Learn more
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Danoprevir.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Danoprevir.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Danoprevir.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Danoprevir.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Danoprevir.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Danoprevir.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Danoprevir.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Danoprevir.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Danoprevir.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Danoprevir.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Evidence Level

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

References

General References
  1. He Y, King MS, Kempf DJ, Lu L, Lim HB, Krishnan P, Kati W, Middleton T, Molla A: Relative replication capacity and selective advantage profiles of protease inhibitor-resistant hepatitis C virus (HCV) NS3 protease mutants in the HCV genotype 1b replicon system. Antimicrob Agents Chemother. 2008 Mar;52(3):1101-10. Epub 2007 Dec 17. [PubMed:18086851]
External Links
PubChem Compound
11285588
PubChem Substance
347828129
ChemSpider
9460579
ChEMBL
CHEMBL258734
Wikipedia
Danoprevir

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers10
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection2
1CompletedTreatmentHealthy Volunteers7
1CompletedTreatmentHealthy Volunteers / Hepatitis C Virus (HCV) Infection1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection9
2WithdrawnTreatmentChronic Hepatitis C Virus (HCV) Infection1
2, 3Active Not RecruitingTreatmentHepatitis C Virus (HCV) Infection1
3CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0413 mg/mLALOGPS
logP2.37ALOGPS
logP2.55ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area180.52 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity181.9 m3·mol-1ChemAxon
Polarizability74.82 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
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 cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Cyclic peptides
Alternative Parents
Macrolactams / Alpha amino acid amides / Isoindoles / Isoindolines / Aryl fluorides / Benzenoids / Cyclopropanecarboxylic acids and derivatives / Tertiary carboxylic acid amides / Pyrrolidines / Organosulfonic acids and derivatives
show 12 more
Substituents
Cyclic alpha peptide / Macrolactam / Alpha-amino acid amide / Alpha-amino acid or derivatives / Isoindoline / Isoindole / Isoindole or derivatives / Aryl fluoride / Aryl halide / Cyclopropanecarboxylic acid or derivatives
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Not Available
Pharmacological action
Unknown
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
P26664
Uniprot Name
Genome polyprotein
Molecular Weight
327198.77 Da

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
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. Drug Interactions & Labeling - FDA [Link]

Drug created on October 20, 2016 14:47 / Updated on May 01, 2019 13:21