EMRICASAN

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12619025 | https://www.ncbi.nlm.nih.gov/pubmed/16250635 | https://www.ncbi.nlm.nih.gov/pubmed/14742742 | http://www.conatuspharma.com/programs/partnered-programs/mechanism-of-action.htm | http://adisinsight.springer.com/drugs/800015246

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

Targets

Primary Target	Pharmacology	Condition	Potency
CHEMBL3831289: Caspase 3 Target ID: CHEMBL3831289: Caspase Sources: https://www.ncbi.nlm.nih.gov/pubmed/16250635 \| http://www.conatuspharma.com/programs/partnered-programs/mechanism-of-action.htm	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Acute myeloid leukemia 136 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27194727	Primary	Basic research	Unknown Approved Use Unknown
Non-alcoholic fatty liver disease 30 Sources: http://adisinsight.springer.com/drugs/800015246 http://www.conatuspharma.com/trials/	Primary	Phase II 1132	Unknown Approved Use Unknown
Liver cirrhosis 15 Sources: http://adisinsight.springer.com/drugs/800015246 http://www.conatuspharma.com/trials/	Primary	Phase II 1132	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1537

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=174006947	no

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
First-in-class pan caspase inhibitor developed for the treatment of liver disease.	2005 Nov 3	16250635

Patents

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

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:40:39 UTC 2023` Edited by `admin` on `Sat Dec 16 17:40:39 UTC 2023`
Record UNII	P0GMS9N47Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EMRICASAN

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