Emopamil

Last updated
Emopamil
Emopamil.png
Names
IUPAC name
2-isopropyl-5-(methyl- (2-phenylethyl)amino)- 2-phenylpentanenitrile
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: DWAWDSVKAUWFHC-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/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
    Key: DWAWDSVKAUWFHC-UHFFFAOYAK
  • N#CC(c1ccccc1)(C(C)C)CCCN(CCc2ccccc2)C
  • CC(C)C(CCCN(C)CCC1=CC=CC=C1)(C#N)C2=CC=CC=C2
Properties
C23H30N2
Molar mass 334.50 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Emopamil is a calcium channel blocker and a high-affinity ligand of human sterol isomerase. [1]

Contents

Structure

Emopamil's structure consists of an organic amino compound, nitrile compound and a member of two benzene rings.

Applications

Emopamil also known as EMP is a phenylalkylamine and inhibitor of 5-hydroxytryptamine 5-HT2 receptors. [2] EMP includes a chiral quaternary carbon center, and research has indicated that its optical isomers have different biological effects. [3] It interacts in an extracellular site of the nerve cell to inhibit calcium channel responses while other phenylalkylamines act at an intracellular site. The interaction site of emopamil suggests to its greater neuroprotective efficacy in research related to ischaemia. [4]

See also

Related Research Articles

Calcium channel blockers (CCB), calcium channel antagonists or calcium antagonists are a group of medications that disrupt the movement of calcium through calcium channels. Calcium channel blockers are used as antihypertensive drugs, i.e., as medications to decrease blood pressure in patients with hypertension. CCBs are particularly effective against large vessel stiffness, one of the common causes of elevated systolic blood pressure in elderly patients. Calcium channel blockers are also frequently used to alter heart rate, to prevent peripheral and cerebral vasospasm, and to reduce chest pain caused by angina pectoris.

<span class="mw-page-title-main">Verapamil</span> Calcium channel blocker medication

Verapamil, sold under various trade names, is a calcium channel blocker medication used for the treatment of high blood pressure, angina, and supraventricular tachycardia. It may also be used for the prevention of migraines and cluster headaches. It is given by mouth or by injection into a vein.

<span class="mw-page-title-main">Amlodipine</span> Dihydropyridine calcium channel blocker used to treat cardiovascular diseases

Amlodipine, sold under the brand name Norvasc among others, is a calcium channel blocker medication used to treat high blood pressure and coronary artery disease. It is taken by mouth.

<span class="mw-page-title-main">Diltiazem</span> Calcium channel blocker medication

Diltiazem, sold under the brand name Cardizem among others, is a calcium channel blocker medication used to treat high blood pressure, angina, and certain heart arrhythmias. It may also be used in hyperthyroidism if beta blockers cannot be used. It is taken by mouth or injection into a vein. When given by injection, effects typically begin within a few minutes and last a few hours.

Voltage-gated calcium channels (VGCCs), also known as voltage-dependent calcium channels (VDCCs), are a group of voltage-gated ion channels found in the membrane of excitable cells (e.g., muscle, glial cells, neurons, etc.) with a permeability to the calcium ion Ca2+. These channels are slightly permeable to sodium ions, so they are also called Ca2+-Na+ channels, but their permeability to calcium is about 1000-fold greater than to sodium under normal physiological conditions.

<span class="mw-page-title-main">Sigma-1 receptor</span> Chaperone protein

The sigma-1 receptor (σ1R), one of two sigma receptor subtypes, is a chaperone protein at the endoplasmic reticulum (ER) that modulates calcium signaling through the IP3 receptor. In humans, the σ1 receptor is encoded by the SIGMAR1 gene.

The P-type calcium channel is a type of voltage-dependent calcium channel. Similar to many other high-voltage-gated calcium channels, the α1 subunit determines most of the channel's properties. The 'P' signifies cerebellar Purkinje cells, referring to the channel's initial site of discovery. P-type calcium channels play a similar role to the N-type calcium channel in neurotransmitter release at the presynaptic terminal and in neuronal integration in many neuronal types.

<span class="mw-page-title-main">N-type calcium channel</span> Protein family

N-type calcium channels also called Cav2.2 channels are voltage gated calcium channels that are localized primarily on the nerve terminals and dendrites as well as neuroendocrine cells. The calcium N-channel consists of several subunits: the primary subunit α1B and the auxiliary subunits α2δ and β. The α1B subunit forms the pore through which the calcium enters and helps to determine most of the channel's properties. These channels play an important role in the neurotransmission during development. In the adult nervous system, N-type calcium channels are critically involved in the release of neurotransmitters, and in pain pathways. N-type calcium channels are the target of ziconotide, the drug prescribed to relieve intractable cancer pain. There are many known N-type calcium channel blockers that function to inhibit channel activity, although the most notable blockers are ω-conotoxins.

<span class="mw-page-title-main">L-type calcium channel</span> Family of transport proteins

The L-type calcium channel is part of the high-voltage activated family of voltage-dependent calcium channel. "L" stands for long-lasting referring to the length of activation. This channel has four isoforms: Cav1.1, Cav1.2, Cav1.3, and Cav1.4.

Ca<sub>v</sub>1.3 Protein-coding gene in the species Homo sapiens

Calcium channel, voltage-dependent, L type, alpha 1D subunit is a protein that in humans is encoded by the CACNA1D gene. Cav1.3 channels belong to the Cav1 family, which form L-type calcium currents and are sensitive to selective inhibition by dihydropyridines (DHP).

<span class="mw-page-title-main">Gallopamil</span> Chemical compound

Gallopamil (INN) is an L-type calcium channel blocker that is an analog of verapamil. It is used in the treatment of abnormal heart rhythms.

<span class="mw-page-title-main">Efonidipine</span> Chemical compound

Efonidipine (INN) is a dihydropyridine calcium channel blocker marketed by Shionogi & Co. of Japan. It was launched in 1995, under the brand name Landel (ランデル). The drug blocks both T-type and L-type calcium channels. Drug Controller General of India (DCGI) has approved the use of efonidipine in India. It is launched under the brand name "Efnocar".

<span class="mw-page-title-main">Devapamil</span> Chemical compound

Devapamil is a calcium channel blocker. It is also known as desmethoxyverapamil, which is a phenylalkylamine (PAA) derivative. Devapamil not only inhibits by blocking the calcium gated channels, but also by depolarizing the membrane during the sodium-potassium exchanges.

<span class="mw-page-title-main">Anipamil</span> Chemical compound

Anipamil is a calcium channel blocker, specifically of the phenylalkylamine type. This type is separate from its more common cousin Dihydropyridine. Anipamil is an analog of the more common drug verapamil, which is the most common type of phenylalkylamine style calcium channel blocker. Anipamil has been shown to be a more effective antiarrhythmic medication than verapamil because it does not cause hypertension as seen in verapamil. It is able to do this by bonding to the myocardium tighter than verapamil.

<span class="mw-page-title-main">Diphenylbutylpiperidine</span> Class of typical antipsychotic drugs

Diphenylbutylpiperidines are a class of typical antipsychotic drugs which were all synthesized, developed, and marketed by Janssen Pharmaceutica.

<span class="mw-page-title-main">BRL-32872</span> Chemical compound

BRL-32872 is an experimental drug candidate that provides a novel approach to the treatment of cardiac arrhythmia. Being a derivative of verapamil, it possesses the ability to inhibit Ca+2 membrane channels. Specific modifications in hydrogen bonding activity, nitrogen lone pair availability, and molecular flexibility allow BRL-32872 to inhibit K+ channels as well. As such, BRL-32872 is classified as both a class III (K+ blocking) and class IV (Ca+2 blocking) antiarrhythmic agent.

<span class="mw-page-title-main">AH-1058</span> Chemical compound

AH-1058 is a lipophilic antiarrhythmic calcium channel blocker synthesized by the Pharmaceutical Research Laboratories of Ajinomoto Co., Inc in Kawasaki, Japan. It is derived from cyproheptadine, a compound with known antiserotonic, antihistaminic and calcium channel blocking properties. The IUPAC name of AH-1058 is: 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-[E-3-(3-methoxy-2-nitro) phenyl-2-propenyl]piperidine hydrochloride.

Fenpropimorph is a morpholine-derived fungicide used in agriculture, primarily on cereal crops such as wheat. It has been reported to disrupt eukaryotic sterol biosynthesis pathways, notably by inhibiting fungal Δ14 reductases. It has also been reported to inhibit mammalian sterol biosynthesis by affecting lanosterol demethylation. Although used in agriculture for pest management purposes, it has been reported to have a strong adverse effect on sterol biosynthesis in higher-plants by inhibiting the cycloeucalenol-obtusifoliol isomerase. This inhibition was shown to not only alter the lipid composition of the plasma-membrane, but also impact cell division and growth, in plants.

<span class="mw-page-title-main">CIM-0216</span> Chemical compound

CIM-0216 is a chemical compound which acts as a potent and selective activator of the TRPM3 calcium channel. It produces nociception and inflammation and is used to study the function of the TRPM3 receptor in these processes.

Dihydropyridine calcium channel blockers are derivatives of 1,4-dihydropyridine that are used as L-type calcium channel blockers. They are used in the treatment of hypertension.

References

  1. ↑ Paul, Raymond; Silve, Sandra; De Nys, Nathalie; Dupuy, Pascal-Henry; Labit-Le Bouteiller, Christine; Rosenfeld, Jorge; Ferrara, Pascual; Le Fur, Gérard; Casellas, Pierre; Loison, Gérard (1998). "Both the Immunosuppressant SR31747 and the Antiestrogen Tamoxifen Bind to an Emopamil-Insensitive Site of Mammalian Δ8-Δ7 Sterol Isomerase". Journal of Pharmacology and Experimental Therapeutics. 285 (3): 1296–302. PMID   9618436.
  2. ↑ "Emopamil - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2022-12-07.
  3. ↑ Toyohara, J.; Okamoto, M.; Aramaki, H.; Zaitsu, Y.; Shimizu, I.; Ishiwata, K. (2016). "(R)-¹¹CEmopamil as a novel tracer for imaging enhanced P-glycoprotein function". Nuclear Medicine and Biology. 43 (1): 52–62. doi:10.1016/j.nucmedbio.2015.09.001. PMID   26429767.
  4. ↑ Keith, R. A.; Mangano, T. J.; Defeo, P. A.; Ernst, G. E.; Warawa, E. J. (1994). "Differential inhibition of neuronal calcium entry and 3H-D-aspartate release by the quaternary derivatives of verapamil and emopamil". British Journal of Pharmacology. 113 (2): 379–384. doi:10.1111/j.1476-5381.1994.tb16999.x. PMC   1510140 . PMID   7834187.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.