Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C23H30N2.ClH |
| Molecular Weight | 370.959 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)C(CCCN(C)CCC1=CC=CC=C1)(C#N)C2=CC=CC=C2
InChI
InChIKey=OBAQQQOVZUCKMH-UHFFFAOYSA-N
InChI=1S/C23H30N2.ClH/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;1H
| 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 | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|
| A novel X-linked multiple congenital anomaly syndrome associated with an EBP mutation. | 2010-11 |
|
| Gene expression profiling and network analysis reveals lipid and steroid metabolism to be the most favored by TNFalpha in HepG2 cells. | 2010-02-04 |
|
| Transcriptional profiling of rats subjected to gestational undernourishment: implications for the developmental variations in metabolic traits. | 2009-09-29 |
|
| Do sex steroids exert sex-specific and/or opposite effects on gene expression in lacrimal and meibomian glands? | 2009-08-10 |
|
| Identifying components of the hair-cell interactome involved in cochlear amplification. | 2009-03-25 |
|
| Genomic and biochemical approaches in the discovery of mechanisms for selective neuronal vulnerability to oxidative stress. | 2009-02-19 |
|
| 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 |
|
| Anticipation in familial lattice corneal dystrophy type I with R124C mutation in the TGFBI (BIGH3) gene. | 2008-05-07 |
|
| Prenatal testing for a novel EBP missense mutation causing X-linked dominant chondrodysplasia punctata. | 2008-05 |
|
| Two novel EBP mutations in Conradi-Hünermann-Happle syndrome. | 2008-02-27 |
|
| A Botrytis cinerea emopamil binding domain protein, required for full virulence, belongs to a eukaryotic superfamily which has expanded in euascomycetes. | 2008-02 |
|
| B-Type natriuretic peptide inhibited angiotensin II-stimulated cholesterol biosynthesis, cholesterol transfer, and steroidogenesis in primary human adrenocortical cells. | 2007-08 |
|
| Functional analysis of cholesterol biosynthesis by RNA interference. | 2007-05 |
|
| Reduced penetrance in a family with X-linked dominant chondrodysplasia punctata. | 2007-02-28 |
|
| Loss of Parp-1 affects gene expression profile in a genome-wide manner in ES cells and liver cells. | 2007-02-07 |
|
| 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 |
|
| Investigation of the phenylalkylamine binding site in hKv1.3 (H399T), a mutant with a reduced C-type inactivated state. | 2005-10 |
|
| Discovery of high-affinity ligands of sigma1 receptor, ERG2, and emopamil binding protein by pharmacophore modeling and virtual screening. | 2005-07-28 |
|
| Molecular prenatal diagnosis in a case of an X-linked dominant chondrodysplasia punctata. | 2003-09 |
|
| Discovery of novel neuronal voltage-dependent calcium channel blockers based on emopamil left hand as a bioactive template. | 2003-03-10 |
|
| X-linked dominant chondrodysplasia punctata (CDPX2) caused by single gene mosaicism in a male. | 2003-01-30 |
|
| 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 |
|
| Characterization of mutations in 22 females with X-linked dominant chondrodysplasia punctata (Happle syndrome). | 2003-01-02 |
|
| Purification, characterization and catalytic properties of human sterol 8-isomerase. | 2002-11-01 |
|
| Isolation of differentially expressed genes in NPM-ALK-positive anaplastic large cell lymphoma. | 2002-09 |
|
| Practical synthesis of chiral emopamil left hand as a bioactive motif. | 2002-08-23 |
|
| Gas chromatography-mass spectrometry and molecular genetic studies in families with the Conradi-Hünermann-Happle syndrome. | 2002-05 |
|
| Mouse Tdho abnormality results from double point mutations of the emopamil binding protein gene (Ebp). | 2001-08 |
|
| 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 |
|
| Postischemic (S)-emopamil therapy ameliorates focal ischemic brain injury in rats. | 1991-03 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Apr 01 20:45:04 GMT 2025
by
admin
on
Tue Apr 01 20:45:04 GMT 2025
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| Record UNII |
N59DRZ2F9U
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| Record Status |
Validated (UNII)
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| Record Version |
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24834486
Created by
admin on Tue Apr 01 20:45:04 GMT 2025 , Edited by admin on Tue Apr 01 20:45:04 GMT 2025
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N59DRZ2F9U
Created by
admin on Tue Apr 01 20:45:04 GMT 2025 , Edited by admin on Tue Apr 01 20:45:04 GMT 2025
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| Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |