EMOPAMIL

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H30N2
Molecular Weight	334.4977
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C(CCCN(C)CCC1=CC=CC=C1)(C#N)C2=CC=CC=C2

InChI

InChIKey=DWAWDSVKAUWFHC-UHFFFAOYSA-N

InChI=1S/C23H30N2/c1-20(2)23(19-24,22-13-8-5-9-14-22)16-10-17-25(3)18-15-21-11-6-4-7-12-21/h4-9,11-14,20H,10,15-18H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C23H30N2
Molecular Weight	334.4977
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2335394 | https://www.ncbi.nlm.nih.gov/pubmed/2458606 | https://www.ncbi.nlm.nih.gov/pubmed/9146879

Emopamil is a phenylalkylamine calcium antagonist. Emopamil has optically active stereoisomers. Emopamil enhanced the postischemic restoration of high-energy phosphate levels. The racemic mixture and the (-)-enantiomer of emopamil caused similar metabolic changes while (+)-enantiomer of emopamil proved to be ineffective. Emopamil is able to reverse multi-drug resistance in human KB cell lines. No differences in reversing potency were observed between emopamil (R)-isomers, (L)-isomers and the racemic form. There is a pharmacological relationship between sigma1-binding site and the mammalian sterol C8-C7 isomerase which is identical with the emopamil binding protein.

Approval Year

PubMed

Title	Date	PubMed
Postischemic (S)-emopamil therapy ameliorates focal ischemic brain injury in rats.	1991 Mar	2003305
Mouse Tdho abnormality results from double point mutations of the emopamil binding protein gene (Ebp).	2001 Aug	11471053
Cholesterol biosynthesis from lanosterol: molecular cloning, chromosomal localization, functional expression and liver-specific gene regulation of rat sterol delta8-isomerase, a cholesterogenic enzyme with multiple functions.	2001 Feb 1	11171067
Practical synthesis of chiral emopamil left hand as a bioactive motif.	2002 Aug 23	12182667
Gas chromatography-mass spectrometry and molecular genetic studies in families with the Conradi-Hünermann-Happle syndrome.	2002 May	11982764
Purification, characterization and catalytic properties of human sterol 8-isomerase.	2002 Nov 1	12133002
Characterization of mutations in 22 females with X-linked dominant chondrodysplasia punctata (Happle syndrome).	2002 Nov-Dec	12509714
Isolation of differentially expressed genes in NPM-ALK-positive anaplastic large cell lymphoma.	2002 Sep	12181047
X-linked dominant chondrodysplasia punctata (CDPX2) caused by single gene mosaicism in a male.	2003 Jan 30	12503102
Molecular, biochemical, and phenotypic analysis of a hemizygous male with a severe atypical phenotype for X-linked dominant Conradi-Hunermann-Happle syndrome and a mutation in EBP.	2003 Jan 30	12503101
Discovery of novel neuronal voltage-dependent calcium channel blockers based on emopamil left hand as a bioactive template.	2003 Mar 10	12617921
Molecular prenatal diagnosis in a case of an X-linked dominant chondrodysplasia punctata.	2003 Sep	12975777
Discovery of high-affinity ligands of sigma1 receptor, ERG2, and emopamil binding protein by pharmacophore modeling and virtual screening.	2005 Jul 28	16033255
Investigation of the phenylalkylamine binding site in hKv1.3 (H399T), a mutant with a reduced C-type inactivated state.	2005 Oct	16000530
Short-term arginine deprivation results in large-scale modulation of hepatic gene expression in both normal and tumor cells: microarray bioinformatic analysis.	2006 Sep 8	16961918
B-Type natriuretic peptide inhibited angiotensin II-stimulated cholesterol biosynthesis, cholesterol transfer, and steroidogenesis in primary human adrenocortical cells.	2007 Aug	17478552
Loss of Parp-1 affects gene expression profile in a genome-wide manner in ES cells and liver cells.	2007 Feb 7	17286852
Functional analysis of cholesterol biosynthesis by RNA interference.	2007 May	17498944
Reduced penetrance in a family with X-linked dominant chondrodysplasia punctata.	2007 Sep-Oct	17625999
Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity.	2008 Dec 11	19053780
A Botrytis cinerea emopamil binding domain protein, required for full virulence, belongs to a eukaryotic superfamily which has expanded in euascomycetes.	2008 Feb	18156289
Two novel EBP mutations in Conradi-Hünermann-Happle syndrome.	2008 Jul-Aug	18573709
Prenatal testing for a novel EBP missense mutation causing X-linked dominant chondrodysplasia punctata.	2008 May	18395876
Anticipation in familial lattice corneal dystrophy type I with R124C mutation in the TGFBI (BIGH3) gene.	2008 May 7	18470323
Do sex steroids exert sex-specific and/or opposite effects on gene expression in lacrimal and meibomian glands?	2009 Aug 10	19693291
Genomic and biochemical approaches in the discovery of mechanisms for selective neuronal vulnerability to oxidative stress.	2009 Feb 19	19228403
Identifying components of the hair-cell interactome involved in cochlear amplification.	2009 Mar 25	19320974
Transcriptional profiling of rats subjected to gestational undernourishment: implications for the developmental variations in metabolic traits.	2009 Sep 29	19787071
Gene expression profiling and network analysis reveals lipid and steroid metabolism to be the most favored by TNFalpha in HepG2 cells.	2010 Feb 4	20140224
A novel X-linked multiple congenital anomaly syndrome associated with an EBP mutation.	2010 Nov	20949533
Conradi-Hünermann-Happle syndrome.	2010 Nov 15	21163155

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:16:07 UTC 2023` Edited by `admin` on `Fri Dec 15 16:16:07 UTC 2023`
Record UNII	M514041RF7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EMOPAMIL

Official Name

English

emopamil [INN]

Common Name

English

2-ISOPROPYL-5-(METHYLPHENETHYLAMINO)-2-PHENYLVALERONITRILE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29707