Page last updated: 2024-12-06

emopamil

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Emopamil is a calcium channel blocker that was originally developed for the treatment of hypertension. It acts by inhibiting the influx of calcium ions into smooth muscle cells, leading to vasodilation and a decrease in blood pressure. However, emopamil was found to have significant side effects, including bradycardia, heart block, and hypotension. As a result, it was withdrawn from the market in many countries.
Despite its clinical limitations, emopamil has continued to be studied for its potential therapeutic effects. Research suggests that emopamil may have neuroprotective properties and could be beneficial in the treatment of neurodegenerative diseases such as Alzheimer's disease. Emopamil has also been investigated for its potential role in the treatment of cancer and pain.
The synthesis of emopamil involves a multi-step process that starts with the preparation of a key intermediate, 4-methoxyphenylacetic acid. This intermediate is then reacted with 2-amino-1-phenylethanol to form the final product. Emopamil is typically administered orally, but it is also available in intravenous form.
While emopamil is not currently approved for use in humans, it remains a subject of ongoing research. Its unique pharmacological properties and potential therapeutic benefits make it an interesting compound for further investigation.'

emopamil: prevents renal injury after warm & cold ischemia; RN given refers to cpd without isomeric designation; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID71225
CHEMBL ID173809
CHEBI ID34736
SCHEMBL ID93921
MeSH IDM0149648

Synonyms (24)

Synonym
emopamil
emopamilum [latin]
emopamilo [spanish]
emopamil [inn]
2-isopropyl-5-(methylphenethylamino)-2-phenylvaleronitrile
78370-13-5
chebi:34736 ,
CHEMBL173809
emopamilo
unii-m514041rf7
emopamilum
m514041rf7 ,
SCHEMBL93921
2-[3-[(phenylethyl)-methylamino]-propyl]-isopropylphenylacetonitrile
DWAWDSVKAUWFHC-UHFFFAOYSA-N
5-[methyl(2-phenylethyl)amino]-2-phenyl-2-(propan-2-yl)pentanenitrile
2-isopropyl-5-[methyl-(2-phenylethyl)amino]-2-phenylpentanenitrile
(+-)emopamil
Q5373671
DB14064
(+/-)-sz 45;racemic emopamil; sz 45
5-[methyl(2-phenylethyl)amino]-2-phenyl-2-propan-2-ylpentanenitrile
()-sz 45;racemic emopamil; sz 45
DTXSID90868474

Research Excerpts

Overview

(S)-Emopamil is a phenylalkylamine-type calcium channel blocker. It exhibits stereoselective antagonism of the serotonin S2 receptor and has excellent blood-brain barrier penetrability.

ExcerptReferenceRelevance
"(S)-Emopamil is a phenylalkylamine-type calcium channel blocker which also exhibits stereoselective antagonism of the serotonin S2 receptor and has excellent blood-brain barrier penetrability."( Calcium antagonists in the treatment of experimental cerebral ischemia.
Busto, R; Dietrich, WD; Ginsberg, MD; Globus, MY; Lin, B; Morikawa, E, 1991
)
0.76
"(S)-Emopamil is a calcium channel blocker of the phenylalkylamine class, having potent serotonin S2 antagonistic properties and high blood-brain barrier penetrability. "( Postischemic (S)-emopamil therapy ameliorates focal ischemic brain injury in rats.
Busto, R; Dietrich, WD; Duncan, RC; Ginsberg, MD; Morikawa, E, 1991
)
1.18
"(S)-Emopamil is a novel calcium channel blocker of the phenylalkylamine class, with potent serotonin S2 antagonist activity. "( (S)-emopamil protects against global ischemic brain injury in rats.
Busto, R; Dietrich, WD; Ginsberg, MD; Lin, BW, 1990
)
1.4
"(S)-Emopamil is a novel calcium channel blocker of the phenylalkylamine class, with superior blood-brain permeability and potent serotonin S2 antagonist activity. "( (S)-emopamil, a novel calcium channel blocker and serotonin S2 antagonist, markedly reduces infarct size following middle cerebral artery occlusion in the rat.
Dietrich, WD; Ginsberg, MD; Nakayama, H, 1988
)
1.39

Effects

ExcerptReferenceRelevance
"(S)-Emopamil has a less potent calcium antagonistic effect (EC50 = 270 nmol/l) on the aorta than verapamil and gallopamil (EC50 = 35 and 14 nmol/l, respectively)."( (S)-emopamil, a novel calcium and serotonin antagonist for the treatment of cerebrovascular disorders. 1st communication: pharmacological profile.
Hofmann, HP; Raschack, M; Unger, L, 1989
)
1.32
"(S)-Emopamil has a less potent calcium antagonistic effect (EC50 = 270 nmol/l) on the aorta than verapamil and gallopamil (EC50 = 35 and 14 nmol/l, respectively)."( (S)-emopamil, a novel calcium and serotonin antagonist for the treatment of cerebrovascular disorders. 1st communication: pharmacological profile.
Hofmann, HP; Raschack, M; Unger, L, 1989
)
1.32

Treatment

ExcerptReferenceRelevance
"(S)-Emopamil pre-treatment, 20 mg/kg i.p., 30 min prior to ischemia, with a second dose 2.5 h later, resulted in 1.8-2.4 fold increases in numbers of surviving CA1 pyramidal neurons."( Calcium antagonists in the treatment of experimental cerebral ischemia.
Busto, R; Dietrich, WD; Ginsberg, MD; Globus, MY; Lin, B; Morikawa, E, 1991
)
0.76
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
organic amino compoundA compound formally derived from ammonia by replacing one, two or three hydrogen atoms by organyl groups.
benzenesAny benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID217471Neuronal voltage-dependent calcium channel (VDCC) inhibitory activity determined in rat cortical synaptosomes2003Bioorganic & medicinal chemistry letters, Mar-10, Volume: 13, Issue:5
Discovery of novel neuronal voltage-dependent calcium channel blockers based on emopamil left hand as a bioactive template.
AID681353TP_TRANSPORTER: increase in Vinblastine intracellular accumulation in F4-6RADR cells1992Biochemical pharmacology, Jun-23, Volume: 43, Issue:12
Stereoisomers of calcium antagonists which differ markedly in their potencies as calcium blockers are equally effective in modulating drug transport by P-glycoprotein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (48)

TimeframeStudies, This Drug (%)All Drugs %
pre-199012 (25.00)18.7374
1990's30 (62.50)18.2507
2000's2 (4.17)29.6817
2010's2 (4.17)24.3611
2020's2 (4.17)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.94

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.94 (24.57)
Research Supply Index3.91 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index27.14 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.94)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (6.12%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other46 (93.88%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]