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
Practical synthesis of chiral emopamil left hand as a bioactive motif.	2002 Aug 23	12182667
Isolation of differentially expressed genes in NPM-ALK-positive anaplastic large cell lymphoma.	2002 Sep	12181047
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
Investigation of the phenylalkylamine binding site in hKv1.3 (H399T), a mutant with a reduced C-type inactivated state.	2005 Oct	16000530
Functional analysis of cholesterol biosynthesis by RNA interference.	2007 May	17498944
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
Identifying components of the hair-cell interactome involved in cochlear amplification.	2009 Mar 25	19320974
Conradi-Hünermann-Happle syndrome.	2010 Nov 15	21163155

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:16:07 GMT 2023` Edited by `admin` on `Fri Dec 15 16:16:07 GMT 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