IMD-0354

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H8ClF6NO2
Molecular Weight	383.673
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(Cl)C=C1C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F

InChI

InChIKey=CHILCFMQWMQVAL-UHFFFAOYSA-N

InChI=1S/C15H8ClF6NO2/c16-9-1-2-12(24)11(6-9)13(25)23-10-4-7(14(17,18)19)3-8(5-10)15(20,21)22/h1-6,24H,(H,23,25)

HIDE SMILES / InChI

Molecular Formula	C15H8ClF6NO2
Molecular Weight	383.673
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16397257
Curator's Comment: description was created based on several sources, including: http://www.immd.co.jp/en/development.html | http://adisinsight.springer.com/drugs/800030091 | https://www.ncbi.nlm.nih.gov/pubmed/15194461

IMD-0354 is an inhibitor of IκB kinase-β (IKKβ) that blocks NF-κB nuclear translocation. Attenuates myocardial ischemia/reperfusion injury by decreasing expression of adhesion molecules ICAM-1 and P-selectin and inhibiting cytokine and chemokine production in cardiomyocytes. Induces G0/G1 cell cycle arrest and apoptosis in HMC-1 and breast cancer cells. IMD-0354 had been in phase I clinical trials for the treatment of atopic dermatitis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Inhibitor of NF-kappa-B kinase (IKK) 3 Target ID: CHEMBL2111328 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25637316 \| http://www.immd.co.jp/en/development.html	Inhibitor 8297		250.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Atopic dermatitis 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17068475 http://adisinsight.springer.com/drugs/800030091	Primary	Phase I 428	Unknown Approved Use Unknown
Allergic asthma 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26868187	Preventing	Preclinical	Unknown Approved Use Unknown
Diabetic retinopathy 17 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25205865	Primary	Preclinical	Unknown Approved Use Unknown
Pulmonary arterial hypertension 35 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23631839	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25637316 https://www.ncbi.nlm.nih.gov/pubmed/24014113 http://www.immd.co.jp/en/development.html	Primary	Preclinical	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461		P-gp 257

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=174007014	yes [IC50 0.1865 uM]
P-gp 1650	inducer 1573 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2841251/	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00378P	https://www.1pchem.com/search?query=1P00378P
AK Scientific	2473AH	https://aksci.com/item_detail.php?cat=2473AH
AOBIOUS INC	AOB5931	http://aobious.com/aobious/search?search_query=AOB5931
Ambeed	A232738	http://www.ambeed.com/search/Search.html?keyword=A232738
Angene	AGN-PC-0LMBCL	http://www.angenechemical.com/productshow/AGN-PC-0LMBCL.html
ApexBio Technology	B1587	https://www.apexbt.com/catalogsearch/result/?q=B1587
AstaTech	C77350	http://astatechinc.com/CPSResult.php?CRNO=C77350
Axon MedChem	2725	https://www.axonmedchem.com/product/2725
BLD Pharm	BD306084	http://www.bldpharm.com/search/Search.html?keyword=BD306084
BOC Sciences	978-62-1	http://www.bocsci.com/description.asp?cas=978-62-1
Cayman Chemical	17290	http://www.caymanchem.com/app/template/Product.vm/catalog/17290
Chem Scene	CS-4922	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-4922
ChemShuttle	141626	https://www.chemshuttle.com/catalogsearch/result/?q=141626
Combi-Blocks	QV-5423	http://www.combi-blocks.com/cgi-bin/find.cgi?QV-5423
KeyOrganics	AS-71319	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-71319
Lab Network	LN00334714	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00334714
MedChem Express	HY-10172	https://www.medchemexpress.com/search.html?q=HY-10172&ft=&fa=&fp=
MolPort	MolPort-003-941-805	https://www.molport.com/shop/molecule-link/MolPort-003-941-805
Molnova	M16886	https://www.molnova.com/en/serch-list.html?keywords=M16886
MuseChem	I005720	https://www.musechem.com/product/I005720.html
Princeton BioMolecular Research	PBMR221705	http://www.princetonbio.com/order_online?common_id=PBMR221705
Selleck Chemicals	S2864	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2864
TargetMol	T6141	https://www.targetmol.com/search?keyword=T6141
Tocris	2611	https://www.tocris.com/search.php?Type=QuickSearch&Value=2611
eMolecules	539558	https://orderbb.emolecules.com/search/#?query=539558
eNovation Chemicals	D501887	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D501887&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-4778959712	https://mcule.com/MCULE-4778959712/

PubMed

Title	Date	PubMed
Inhibition of IkappaB phosphorylation in cardiomyocytes attenuates myocardial ischemia/reperfusion injury.	2004 Jul 1	15194461
Inhibition of the activation of nuclear factor kappa B to reduce myocardial reperfusion injury and infarct size.	2004 Jul 1	15194456
A novel IKKbeta inhibitor stimulates adiponectin levels and ameliorates obesity-linked insulin resistance.	2004 Oct 8	15351728
A new IkappaB kinase beta inhibitor prevents human breast cancer progression through negative regulation of cell cycle transition.	2006 Jan 1	16397257
Mechanism of signal transduction in tumor necrosis factor-like weak inducer of apoptosis-induced matrix degradation by MMP-3 upregulation in disc tissues.	2008 Nov 1	18923335
Antiallergic and anti-inflammatory effects of a novel I kappaB kinase beta inhibitor, IMD-0354, in a mouse model of allergic inflammation.	2009	18849610
A novel NF-κB inhibitor improves glucocorticoid sensitivity of canine neoplastic lymphoid cells by up-regulating expression of glucocorticoid receptors.	2010 Dec	20362310
Poly(I:C) reduces expression of JAM-A and induces secretion of IL-8 and TNF-α via distinct NF-κB pathways in human nasal epithelial cells.	2011 Jan 1	20932985
Activation of nuclear factor-κB pathway is responsible for tumor necrosis factor-α-induced up-regulation of endothelin B2 receptor expression in vascular smooth muscle cells in vitro.	2012 Mar 7	22207076
Salicylanilide inhibitors of Toxoplasma gondii.	2012 Oct 11	22970937
Structure-activity relationships of antitubercular salicylanilides consistent with disruption of the proton gradient via proton shuttling.	2013 Jan 1	23211970

Patents

Sample Use Guides

In Vivo Use Guide

1, 5, or 10 mg/kg intraperitoneal injection in a single bolus 5 min before the start of reperfusion.

Route of Administration: Other

In Vitro Use Guide

IMD-0354 (0.1-1 uM) caused a significant reduction of both IL-1β (−77%) and MCP-1 (−76%) production in a concentration-dependent manner compared with vehicle-treated cells.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:58:30 GMT 2023` Edited by `admin` on `Sat Dec 16 07:58:30 GMT 2023`
Record UNII	76145IS906
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IMD-0354

Common Name

English

3',5'-SALICYLOXYLIDIDE, 5-CHLORO-.ALPHA.,.ALPHA.,.ALPHA.,.ALPHA.',.ALPHA.',.ALPHA.'-HEXAFLUORO-

Systematic Name

English

BENZAMIDE, N-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-5-CHLORO-2-HYDROXY-

Systematic Name

English

N-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-5-CHLORO-2-HYDROXYBENZAMIDE

Systematic Name

English

Code System Code Type Description

ChEMBL

CHEMBL3545089