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
Conradi-Hünermann-Happle syndrome.	2010-11-15	21163155
A novel X-linked multiple congenital anomaly syndrome associated with an EBP mutation.	2010-11	20949533
Gene expression profiling and network analysis reveals lipid and steroid metabolism to be the most favored by TNFalpha in HepG2 cells.	2010-02-04	20140224
Transcriptional profiling of rats subjected to gestational undernourishment: implications for the developmental variations in metabolic traits.	2009-09-29	19787071
Do sex steroids exert sex-specific and/or opposite effects on gene expression in lacrimal and meibomian glands?	2009-08-10	19693291
Identifying components of the hair-cell interactome involved in cochlear amplification.	2009-03-25	19320974
Genomic and biochemical approaches in the discovery of mechanisms for selective neuronal vulnerability to oxidative stress.	2009-02-19	19228403
Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity.	2008-12-11	19053780
Anticipation in familial lattice corneal dystrophy type I with R124C mutation in the TGFBI (BIGH3) gene.	2008-05-07	18470323
Prenatal testing for a novel EBP missense mutation causing X-linked dominant chondrodysplasia punctata.	2008-05	18395876
Two novel EBP mutations in Conradi-Hünermann-Happle syndrome.	2008-02-27	18573709
A Botrytis cinerea emopamil binding domain protein, required for full virulence, belongs to a eukaryotic superfamily which has expanded in euascomycetes.	2008-02	18156289
B-Type natriuretic peptide inhibited angiotensin II-stimulated cholesterol biosynthesis, cholesterol transfer, and steroidogenesis in primary human adrenocortical cells.	2007-08	17478552
Functional analysis of cholesterol biosynthesis by RNA interference.	2007-05	17498944
Reduced penetrance in a family with X-linked dominant chondrodysplasia punctata.	2007-02-28	17625999
Loss of Parp-1 affects gene expression profile in a genome-wide manner in ES cells and liver cells.	2007-02-07	17286852
Short-term arginine deprivation results in large-scale modulation of hepatic gene expression in both normal and tumor cells: microarray bioinformatic analysis.	2006-09-08	16961918
Investigation of the phenylalkylamine binding site in hKv1.3 (H399T), a mutant with a reduced C-type inactivated state.	2005-10	16000530
Discovery of high-affinity ligands of sigma1 receptor, ERG2, and emopamil binding protein by pharmacophore modeling and virtual screening.	2005-07-28	16033255
Molecular prenatal diagnosis in a case of an X-linked dominant chondrodysplasia punctata.	2003-09	12975777
Discovery of novel neuronal voltage-dependent calcium channel blockers based on emopamil left hand as a bioactive template.	2003-03-10	12617921
X-linked dominant chondrodysplasia punctata (CDPX2) caused by single gene mosaicism in a male.	2003-01-30	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.	2003-01-30	12503101
Characterization of mutations in 22 females with X-linked dominant chondrodysplasia punctata (Happle syndrome).	2003-01-02	12509714
Purification, characterization and catalytic properties of human sterol 8-isomerase.	2002-11-01	12133002
Isolation of differentially expressed genes in NPM-ALK-positive anaplastic large cell lymphoma.	2002-09	12181047
Practical synthesis of chiral emopamil left hand as a bioactive motif.	2002-08-23	12182667
Gas chromatography-mass spectrometry and molecular genetic studies in families with the Conradi-Hünermann-Happle syndrome.	2002-05	11982764
Mouse Tdho abnormality results from double point mutations of the emopamil binding protein gene (Ebp).	2001-08	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.	2001-02-01	11171067
Postischemic (S)-emopamil therapy ameliorates focal ischemic brain injury in rats.	1991-03	2003305

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:23:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:23:31 GMT 2025`
Record UNII	M514041RF7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

emopamil [INN]

Preferred Name

English

EMOPAMIL

Official Name

English

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

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29707