ENIPORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H16N4O3S
Molecular Weight	320.367
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(C=C(C(=C1)N2C=CC=C2)S(C)(=O)=O)C(=O)NC(N)=N

InChI

InChIKey=UADMBZFZZOBWBB-UHFFFAOYSA-N

InChI=1S/C14H16N4O3S/c1-9-7-11(18-5-3-4-6-18)12(22(2,20)21)8-10(9)13(19)17-14(15)16/h3-8H,1-2H3,(H4,15,16,17,19)

HIDE SMILES / InChI

Molecular Formula	C14H16N4O3S
Molecular Weight	320.367
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/11704395
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/9207943 | http://adisinsight.springer.com/drugs/800010029

Eniporide belongs to the new class of drugs that specifically inhibit the Sodium/hydrogen exchanger 1 (NHE-1) isoform, which is the predominant isoform in the cardiac myocytes. Extensive preclinical studies, in vitro and in animals, have suggested that NHE inhibition with eniporide before the onset of ischemia is a very effective and reproducible means of limiting the extent of infarction and that this agent provides protective benefit even when given just before reperfusion. Eniporide had been in phase II clinical trial for the treatment of myocardial infarction. Administration of the eniporide, before reperfusion therapy in patients with acute ST-elevation myocardial infarction, did not limit infarct size or improve clinical outcome.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sodium/hydrogen exchanger 1 12 Target ID: P23791 Gene ID: 1.00009584E8 Gene Symbol: SLC9A1 Target Organism: Oryctolagus cuniculus (Rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9207943 \| https://www.ncbi.nlm.nih.gov/pubmed/11704395	Inhibitor 8297	10.0 nM [IC50]
Sodium/hydrogen exchanger 2 9 Target ID: P50482 Gene ID: NA Gene Symbol: SLC9A2 Target Organism: Oryctolagus cuniculus (Rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9207943	Inhibitor 8297	270.0 nM [IC50]
Sodium/hydrogen exchanger 3 5 Target ID: P26432 Gene ID: 1.00009432E8 Gene Symbol: SLC9A3 Target Organism: Oryctolagus cuniculus (Rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9207943	Inhibitor 8297	700.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Myocardial infarction 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11704395 https://www.ncbi.nlm.nih.gov/pubmed/14564324 https://www.ncbi.nlm.nih.gov/pubmed/9207943	Preventing		Phase II 1132	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
200 mg 1 times / day multiple, intravenous (unknown) Highest studied dose,Studied dose Dose: 200 mg, 1 times / day Route: intravenous Route: multiple Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11704395	unhealthy n = 91 Health Status: unhealthy Condition: acute myocardial infarction Sex: M+F Food Status: UNKNOWN Population Size: 91 Sources: https://pubmed.ncbi.nlm.nih.gov/11704395	Sources: https://pubmed.ncbi.nlm.nih.gov/11704395

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C19 991

Drug as victim

Target	Modality	Activity
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11408372/	yes
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11408372/	yes
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11408372/	yes
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11408372/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY445462	https://www.001chemical.com/chem/search?q=DY445462
1PlusChem LLC	1P01EOYM	https://www.1pchem.com/search?query=1P01EOYM
AChemBlock	10213	http://www.achemblock.com/catalogsearch/result/?q=10213
AK Scientific	9260AA	https://aksci.com/item_detail.php?cat=9260AA
Ambeed	A393479	http://www.ambeed.com/search/Search.html?keyword=A393479
ApexBio Technology	C3709	https://www.apexbt.com/catalogsearch/result/?q=C3709
AstaTech	C10170	http://astatechinc.com/CPSResult.php?CRNO=C10170
Cayman Chemical	20984	http://www.caymanchem.com/app/template/Product.vm/catalog/20984
Chem Scene	CS-7831	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7831
Combi-Blocks	QP-1939	http://www.combi-blocks.com/cgi-bin/find.cgi?QP-1939
Excenen	EX-A1476	http://www.excenen.com/searchresultlist.php?id=EX-A1476
Fluorochem	233849	http://www.fluorochem.co.uk/Products/Product?code=233849
Fluorochem	316940	http://www.fluorochem.co.uk/Products/Product?code=316940
KeyOrganics	DS-16493	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-16493
Lab Network	LN00337357	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00337357
MedChem Express	HY-106150B	https://www.medchemexpress.com/search.html?q=HY-106150B&ft=&fa=&fp=
MolPort	MolPort-023-334-344	https://www.molport.com/shop/molecule-link/MolPort-023-334-344
MolPort	MolPort-035-675-643	https://www.molport.com/shop/molecule-link/MolPort-035-675-643
MolPort	MolPort-046-416-862	https://www.molport.com/shop/molecule-link/MolPort-046-416-862
Molcore	MC445462	http://www.molcore.com/CatMC445462.html
Molnova	M12661	https://www.molnova.com/en/serch-list.html?keywords=M12661
MuseChem	M032654	https://www.musechem.com/product/M032654.html
ShangHai Biochempartner	BCP001187	http://www.biochempartner.com/search_BCP001187
ShangHai Biochempartner	BCP09780	http://www.biochempartner.com/search_BCP09780
TargetMol	T2089	https://www.targetmol.com/search?keyword=T2089
Wonderchem	WD05FCS	http://www.wonder-chem.com/search.html?text=WD05FCS
eMolecules	44471143	https://orderbb.emolecules.com/search/#?query=44471143
eMolecules	49841518	https://orderbb.emolecules.com/search/#?query=49841518
eMolecules	85163699	https://orderbb.emolecules.com/search/#?query=85163699
eNovation Chemicals	D508987	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D508987&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1802182842	https://mcule.com/MCULE-1802182842/
mcule	MCULE-8921314133	https://mcule.com/MCULE-8921314133/

PubMed

Title	Date	PubMed
(2-Methyl-5-(methylsulfonyl)benzoyl)guanidine Na+/H+ antiporter inhibitors.	1997 Jun 20	9207943
Zoniporide: a potent and highly selective inhibitor of human Na(+)/H(+) exchanger-1.	2002 Sep 6	12223226
An overview of inhibitors of Na(+)/H(+) exchanger.	2003 Jun	12832126

Patents

Sample Use Guides

In Vivo Use Guide

100mg or 150 mg

Route of Administration: Intravenous

In Vitro Use Guide

Eniporide (3 uM) and/or lidocaine (200 uM) were administered during 5 min prior to 40 min of global ischemia of isolated rat hearts and 40 min of drug free reperfusion to block the Na( )/H( ) exchanger and the Na( ) channel, respectively. Lidocaine reduced the rise in [Na( )](i) during the first 10 min of ischemia, followed by a rise with a rate similar to the one found in untreated hearts. Eniporide reduced the ischemic Na( ) influx during the entire ischemic period. Administration of both drugs resulted in a summation of the effects found in the lidocaine and eniporide groups. Contractile recovery and infarct size were significantly improved in hearts treated with both drugs, although not significantly different from hearts treated with either one of them.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:17:32 GMT 2023` Edited by `admin` on `Fri Dec 15 16:17:32 GMT 2023`
Record UNII	7IGF9182QU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENIPORIDE

Official Name

English

Eniporide [WHO-DD]

Common Name

English

eniporide [INN]

Common Name

English

N-(DIAMINOMETHYLENE)-5-(METHYLSULFONYL)-4-PYRROL-1-YL-O-TOLUAMIDE

Common Name

English

EMD-96785

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C47793