Identification
NameEmricasan
Accession NumberDB05408
TypeSmall Molecule
GroupsInvestigational
Description

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.

Structure
Thumb
SynonymsNot Available
External IDs IDN 6556 / IDN-6556 / PF-3491390
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIP0GMS9N47Q
CAS numberNot Available
WeightAverage: 569.51
Monoisotopic: 569.178512873
Chemical FormulaC26H27F4N3O7
InChI KeySCVHJVCATBPIHN-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[[email protected]](NC(=O)C(=O)NC1=CC=CC=C1C(C)(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)COC1=C(F)C(F)=CC(F)=C1F
Pharmacology
Indication

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

Structured Indications Not Available
PharmacodynamicsNot 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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Caspase-1ProteinunknownNot AvailableHumanP29466 details
Caspase-3ProteinunknownNot AvailableHumanP42574 details
Caspase-7ProteinunknownNot AvailableHumanP55210 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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. [PubMed:17654603 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentDigestive System Diseases / Hepatic Impairment / Liver Diseases1
1CompletedTreatmentImpaired Renal Function / Kidney Diseases1
1, 2CompletedTreatmentDiabetes1
2Active Not RecruitingTreatmentFibrosis, Liver / Hepatic Cirrhosis / Hepatic Fibrosis / Liver Cirrhosis1
2CompletedTreatmentCholestasis / Hepatitis / Hepatocellular,Carcinoma / Transplantation, Liver1
2CompletedTreatmentHepatic Cirrhosis / Liver Cirrhosis1
2CompletedTreatmentHepatic Cirrhosis / Liver Cirrhosis / Portal Hypertension1
2CompletedTreatmentHepatitis C, Chronic1
2CompletedTreatmentNon-Alcoholic Fatty Liver Disease (NAFLD) / Nonalcoholic Steatohepatitis1
2RecruitingTreatmentCirrhosis, Decompensated1
2RecruitingTreatmentFibrosis / Liver Diseases / Non-Alcoholic Steatohepatitis1
2RecruitingTreatmentLiver Cirrhosis / Non-Alcoholic Steatohepatitis / Portal Hypertension1
2TerminatedTreatmentAcute Alcoholic Hepatitis / Acute on Chronic Hepatic Failure / Fulminant Hepatic Failure / Liver Cirrhosis1
2TerminatedTreatmentAlcoholic Hepatitis (AH)1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Polarizability51.13 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative ParentsN-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
SubstituentsHybrid peptide / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alanine or derivatives / Beta amino acid or derivatives / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Anilide / Phenylpropane / Phenoxy compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
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. Cleaves and activates sterol regulatory element binding proteins (SREBPs). Can also promote apoptosis.
Gene Name:
CASP1
Uniprot ID:
P29466
Uniprot Name:
Caspase-1
Molecular Weight:
45158.215 Da
Kind
Protein
Organism
Human
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' bond. Cleaves and activates sterol regulatory element binding proteins (SREBPs) between the basic helix-loop-helix leucine zipper domain and the membrane attachment domain. Cleaves and activates caspa...
Gene Name:
CASP3
Uniprot ID:
P42574
Uniprot Name:
Caspase-3
Molecular Weight:
31607.58 Da
Kind
Protein
Organism
Human
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-ribose) polymerase (PARP) at a '216-Asp-|-Gly-217' bond. Overexpression promotes programmed cell death.
Gene Name:
CASP7
Uniprot ID:
P55210
Uniprot Name:
Caspase-7
Molecular Weight:
34276.48 Da
Drug created on November 18, 2007 11:24 / Updated on June 24, 2017 13:24