NAV

Emricasan

Identification

Generic Name
Emricasan
DrugBank Accession Number
DB05408
Background

Emricasan is the first caspase inhibitor tested in human which has received orphan drug status by FDA. It is developed by Pfizer and made in such a way that it protects liver cells from excessive apoptosis.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 569.51
Monoisotopic: 569.178512873
Chemical Formula
C26H27F4N3O7
Synonyms
  • Emricasan
  • Emricasán
  • Emricasanum
External IDs
  • IDN 6556
  • IDN-6556
  • IDN6556
  • PF-3491390
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Investigated for use/treatment in hepatitis (viral, C), liver disease, and transplantation (organ or tissue).

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action

IDN-6556 significantly improves markers of liver damage in patients infected with the Hepatitis C virus (HCV), an infection that affects up to 170m patients worldwide. IDN-6556 represents a new class of drugs that protect the liver from inflammation and cellular damage induced by viral infections and other causes. Various studies have also shown that it significantly lowers aminotransferase activity in HCV patients and appeared to be well tolerated.

TargetActionsOrganism
UCaspase-1Not AvailableHumans
UCaspase-3Not AvailableHumans
UCaspase-7Not AvailableHumans
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
Not Available
Food Interactions
Not Available

Categories

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
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Alanine and derivatives / Beta amino acids and derivatives / Phenylpropanes / Anilides / Phenoxy compounds / Phenol ethers / N-arylamides / Gamma-keto acids and derivatives
show 12 more
Substituents
Alanine or derivatives / Alkyl aryl ether / Alpha-amino acid amide / Alpha-amino acid or derivatives / Anilide / Aromatic homomonocyclic compound / Aryl fluoride / Aryl halide / Benzenoid / Beta amino acid or derivatives
show 30 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
P0GMS9N47Q
CAS number
254750-02-2
InChI Key
SCVHJVCATBPIHN-SJCJKPOMSA-N
InChI
InChI=1S/C26H27F4N3O7/c1-12(31-24(38)25(39)32-16-8-6-5-7-13(16)26(2,3)4)23(37)33-17(10-19(35)36)18(34)11-40-22-20(29)14(27)9-15(28)21(22)30/h5-9,12,17H,10-11H2,1-4H3,(H,31,38)(H,32,39)(H,33,37)(H,35,36)/t12-,17-/m0/s1
IUPAC Name
(3S)-3-[(2S)-2-{[(2-tert-butylphenyl)carbamoyl]formamido}propanamido]-4-oxo-5-(2,3,5,6-tetrafluorophenoxy)pentanoic acid
SMILES
C[C@H](NC(=O)C(=O)NC1=C(C=CC=C1)C(C)(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)COC1=C(F)C(F)=CC(F)=C1F

References

General References
  1. Pockros PJ, Schiff ER, Shiffman ML, McHutchison JG, Gish RG, Afdhal NH, Makhviladze M, Huyghe M, Hecht D, Oltersdorf T, Shapiro DA: Oral IDN-6556, an antiapoptotic caspase inhibitor, may lower aminotransferase activity in patients with chronic hepatitis C. Hepatology. 2007 Aug;46(2):324-9. [Article]
PubChem Compound
12000240
PubChem Substance
347827726
ChemSpider
10172707
ChEMBL
CHEMBL197672
ZINC
ZINC000014191207
Wikipedia
Emricasan

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentCholestasis / Hepatitis / Hepatocellular Carcinoma / Liver Transplantation1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2CompletedTreatmentCirrhosis of the Liver1
2CompletedTreatmentCirrhosis of the Liver / Fibrosis, Liver / Hepatic Fibrosis1
2CompletedTreatmentCirrhosis of the Liver / Non Alcoholic Steatohepatitis (NASH) / Portal Hypertension2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00213 mg/mLALOGPS
logP3.48ALOGPS
logP3.42Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.51Chemaxon
pKa (Strongest Basic)-4.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area150.9 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity132.39 m3·mol-1Chemaxon
Polarizability51.56 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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/MSsplash10-0udj-2792150000-748c02bda04a06ac069c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-2139030000-74dc0ed76285eaf7002b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-1942010000-4fada92a5f85949e385f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-2119000000-d73bd83a616c48007e8d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-1951020000-d4480b68bf3a02843bea
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002g-9544000000-2b272f8e55e61682604a
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-226.81078
predicted
DeepCCS 1.0 (2019)
[M+H]+228.90532
predicted
DeepCCS 1.0 (2019)
[M+Na]+234.65422
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
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
Details1. Caspase-1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Endopeptidase activity
Specific Function
Thiol protease that cleaves IL-1 beta between an Asp and an Ala, releasing the mature cytokine which is involved in a variety of inflammatory processes. Important for defense against pathogens. Cle...
Gene Name
CASP1
Uniprot ID
P29466
Uniprot Name
Caspase-1
Molecular Weight
45158.215 Da
Details2. Caspase-3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipase a2 activator activity
Specific Function
Involved in the activation cascade of caspases responsible for apoptosis execution. At the onset of apoptosis it proteolytically cleaves poly(ADP-ribose) polymerase (PARP) at a '216-Asp-|-Gly-217' ...
Gene Name
CASP3
Uniprot ID
P42574
Uniprot Name
Caspase-3
Molecular Weight
31607.58 Da
Details3. Caspase-7
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Cysteine-type peptidase activity
Specific Function
Involved in the activation cascade of caspases responsible for apoptosis execution. Cleaves and activates sterol regulatory element binding proteins (SREBPs). Proteolytically cleaves poly(ADP-ribos...
Gene Name
CASP7
Uniprot ID
P55210
Uniprot Name
Caspase-7
Molecular Weight
34276.48 Da

Drug created at November 18, 2007 18:24 / Updated at February 21, 2021 18:51