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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H27F4N3O7
Molecular Weight 569.5021
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EMRICASAN

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)COC2=C(F)C(F)=CC(F)=C2F

InChI

InChIKey=SCVHJVCATBPIHN-SJCJKPOMSA-N
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

HIDE SMILES / InChI
Molecular Formula C26H27F4N3O7
Molecular Weight 569.5021
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Emricasan (IDN- 6556 or PF-03491390) (3-[2-[(2-tert-butyl-phenylaminooxalyl)-amino]-propionylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid) is a pan-caspase inhibitor. Testing in vitro enzyme assays demonstrated that emricasan efficiently inhibits all human caspases at low nanomolar concentrations. Preclinically, emricasan was effective in inhibiting apoptosis of sinusoidal endothelial cells. Emricasan has marked efficacy in models of liver disease after oral administration and thus, is an excellent candidate for the treatment of liver diseases characterized by excessive apoptosis. This drug is a first-in-class anti-apoptotic caspase inhibitor with demonstrated preliminary efficacy in liver-impaired patients in humans.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Disc. AE: Cellulitis...
Other AEs: Drug hypersensitivity, Sepsis...
AEs leading to
discontinuation/dose reduction:
Cellulitis (serious, 1.9%)
Other AEs:
Drug hypersensitivity (serious, 0.9%)
Sepsis (serious, 0.9%)
Deep vein thrombosis (serious, 0.9%)
Myoclonus (serious, 0.9%)
Inguinal hernia (serious, 0.9%)
Hypersensitivity (serious, 0.9%)
Biliary dyskinesia (serious, 0.9%)
Colitis (serious, 0.9%)
Intestinal perforatio (serious, 0.9%)
Enteritis (serious, 0.9%)
Non-cardiac chest pain (serious, 0.9%)
Urosepsis (serious, 0.9%)
Wound dehiscence (serious, 0.9%)
Pneumonia aspiration (serious, 0.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
AEs

AEs

AESignificanceDosePopulation
Biliary dyskinesia serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Colitis serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Deep vein thrombosis serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Drug hypersensitivity serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Enteritis serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Hypersensitivity serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Inguinal hernia serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Intestinal perforatio serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Myoclonus serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Non-cardiac chest pain serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Pneumonia aspiration serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Sepsis serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Urosepsis serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Wound dehiscence serious, 0.9%
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Cellulitis serious, 1.9%
Disc. AE
50 mg 2 times / day multiple, oral (unknown)
Highest studied dose
Dose: 50 mg, 2 times / day
Route: oral
Route: multiple
Dose: 50 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
unhealthy, ADULT
n = 106
Health Status: unhealthy
Condition: non-alcoholic steatohepatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 106
Sources:
https://pubmed.ncbi.nlm.nih.gov/31887369
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1537
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY100727
https://www.001chemical.com/chem/search?q=DY100727
1PlusChem LLC
1P00C59N
https://www.1pchem.com/search?query=1P00C59N
AChemBlock
M15389
http://www.achemblock.com/catalogsearch/result/?q=M15389
AK Scientific
2073AB
https://aksci.com/item_detail.php?cat=2073AB
AstaTech
43293
http://astatechinc.com/CPSResult.php?CRNO=43293
BLD Pharm
BD210775
http://www.bldpharm.com/search/Search.html?keyword=BD210775
ChemShuttle
139677
https://www.chemshuttle.com/catalogsearch/result/?q=139677
Excenen
EX-A1659
http://www.excenen.com/searchresultlist.php?id=EX-A1659
Hairui
HR109911
http://www.hairuichem.com/en/product/search.do?q=HR109911
KeyOrganics
AS-75073
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-75073
Matrix Scientific
98418
http://www.matrixscientific.com/098418.html
MedChem Express
HY-10396
https://www.medchemexpress.com/search.html?q=HY-10396&ft=&fa=&fp=
MolPort
MolPort-027-835-564
https://www.molport.com/shop/molecule-link/MolPort-027-835-564
Molcore
MC100727
http://www.molcore.com/CatMC100727.html
Molnova
M13761
https://www.molnova.com/en/serch-list.html?keywords=M13761
MuseChem
I002870
https://www.musechem.com/product/I002870.html
ShangHai Biochempartner
BCP07463
http://www.biochempartner.com/search_BCP07463
Sigma Aldrich
SML2227
http://www.sigmaaldrich.com/catalog/search?term=SML2227&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
TargetMol
T6826
https://www.targetmol.com/search?keyword=T6826
Toronto Research Chemicals
E525300
https://www.trc-canada.com/product-detail/?CatNum=E525300
eMolecules
44689873
https://orderbb.emolecules.com/search/#?query=44689873
eNovation Chemicals
D621777
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D621777&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-8169752199
https://mcule.com/MCULE-8169752199/
mcule
MCULE-8346407939
https://mcule.com/MCULE-8346407939/
PubMed

PubMed

TitleDatePubMed
First-in-class pan caspase inhibitor developed for the treatment of liver disease.
2005 Nov 3
Patents

Patents

WO2015175381A1
1

Sample Use Guides

In Vivo Use Guide
Double-blind, randomized, placebo-controlled, parallel-dose study in patients with chronic hepatitis C treated with placebo or Emricasan (IDN- 6556 or PF-03491390) (5, 25 or 50 mg) orally twice daily (b.d.) for up to 12 weeks.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: acute myeloid leukemia (AML) cells are sensitive to birinapant-induced death and that the clinical caspase inhibitor emricasan/IDN-6556 augments, rather than prevents, killing by birinapant. Deletion of caspase-8 sensitized AML to birinapant, whereas combined loss of caspase-8 and the necroptosis effector MLKL (mixed lineage kinase domain-like) prevented birinapant/IDN-6556-induced death, showing that inhibition of caspase-8 sensitizes AML cells to birinapant-induced necroptosis.
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:40:39 GMT 2023
Edited
by admin
on Sat Dec 16 17:40:39 GMT 2023
Record UNII
P0GMS9N47Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EMRICASAN
INN   USAN  
USAN   INN  
Official Name English
L-ALANINAMIDE, N-(2-(1,1-DIMETHYLETHYL)PHENYL)-2-OXOGLYCYL-N-((1S)-1-(CARBOXYMETHYL)-2-OXO-3-(2,3,5,6-TETRAFLUOROPHENOXY)PROPYL)-
Systematic Name English
IDN 6556
Code English
PF 03491390
Code English
VAY-785
Code English
emricasan [INN]
Common Name English
EMRICASAN [USAN]
Common Name English
PF-03491390
Code English
(3S)-3-(N2-((2-TERT-BUTYLPHENYL)OXAMOYL)-L-ALANINAMIDO)-4-OXO-5-(2,3,5,6-TETRAFLUOROPHENOXY)PENTANOIC ACID
Systematic Name English
(3S)-3-((2S)-2-((N-(2-TERT-BUTYL)PHENYL)CARBAMOYL)CARBONYLAMINO) PROPANOYLAMINO)-4-OXO-5-(2,3,5,6-TETRAFLUOROPHENOXY)PENTANOIC ACID
Systematic Name English
Emricasan [WHO-DD]
Common Name English
IDN-6556
Code English
VAY785
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 169603
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
FDA ORPHAN DRUG 396113
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
NCI_THESAURUS C471
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
Code System Code Type Description
WIKIPEDIA
Emricasan
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
FDA UNII
P0GMS9N47Q
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
DRUG BANK
DB05408
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL197672
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
SMS_ID
100000175113
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
PUBCHEM
12000240
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
INN
8960
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
NCI_THESAURUS
C76660
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID10180160
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
CAS
254750-02-2
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
USAN
TT-62
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
PRIMARY
CAS
624747-15-5
Created by admin on Sat Dec 16 17:40:39 GMT 2023 , Edited by admin on Sat Dec 16 17:40:39 GMT 2023
SUPERSEDED
Related Record Type Details
CASPASE-8
TARGET -> INHIBITOR
Related Record Type Details
Structure of EMRICASAN
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
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HHS VULNERABILITY DISCLOSURE
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