devapamil
{{chembox
| ImageFile=Devapamil.svg
| ImageSize=
| IUPACName=(RS)-2-(3,4-dimethoxyphenyl)-2-isopropyl-5-[2-(3-methoxyphenyl)ethyl-methylamino]pentanenitrile
| OtherNames=
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M6142PTV7J
| ChemSpiderID = 59244
| InChI = 1/C26H36N2O3/c1-20(2)26(19-27,22-11-12-24(30-5)25(18-22)31-6)14-8-15-28(3)16-13-21-9-7-10-23(17-21)29-4/h7,9-12,17-18,20H,8,13-16H2,1-6H3
| InChIKey = VMVKIDPOEOLUFS-UHFFFAOYAV
| CASNo=92302-55-1
| PubChem= 65832
| ChEMBL = 2074792
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 34673
| SMILES = N#CC(c1cc(OC)c(OC)cc1)(CCCN(CCc2cccc(OC)c2)C)C(C)C
}}
|Section2={{Chembox Properties
| C=26 | H=36 | N=2 | O=3
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| Density=
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|Section3={{Chembox Hazards
| MainHazards=
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Devapamil is a calcium channel blocker. It is also known as desmethoxyverapamil, which is a phenylalkylamine (PAA) derivative.{{cite journal | vauthors = Erdmann R, Lüttgau HC | title = The effect of the phenylalkylamine D888 (devapamil) on force and Ca2+ current in isolated frog skeletal muscle fibres | journal = The Journal of Physiology | volume = 413 | issue = 1 | pages = 521–41 | date = June 1989 | pmid = 2557440 | doi = 10.1113/jphysiol.1989.sp017667 | pmc = 1189114 }} Devapamil not only inhibits by blocking the calcium gated channels, but also by depolarizing the membrane during the sodium-potassium exchanges.{{cite journal | vauthors = Dierkes PW, Wende V, Hochstrate P, Schlue WR | title = L-type Ca2+ channel antagonists block voltage-dependent Ca2+ channels in identified leech neurons | journal = Brain Research | volume = 1013 | issue = 2 | pages = 159–67 | date = July 2004 | pmid = 15193524 | doi = 10.1016/j.brainres.2004.03.038 | s2cid = 22004238 }}
Structure
Devapamil consists of two aromatic rings with methoxy substituents connected by an alkylamine chain increasing flexibility and overall potency.{{cite journal | vauthors = Cheng RC, Tikhonov DB, Zhorov BS | title = Structural model for phenylalkylamine binding to L-type calcium channels | journal = The Journal of Biological Chemistry | volume = 284 | issue = 41 | pages = 28332–42 | date = October 2009 | pmid = 19700404 | pmc = 2788883 | doi = 10.1074/jbc.M109.027326 | doi-access = free }}
Animal studies
Devapamil in rats can be used to decrease glutathione levels and increase oxidation of lipids, which makes it effective in preclusion of ulcers caused by stress.{{cite journal | vauthors = Alican I, Toker F, Arbak S, Yegen BC, Yalçin AS, Oktay S | title = Gastric lipid peroxidation, glutathione and calcium channel blockers in the stress-induced ulcer model in rats | journal = Pharmacological Research | volume = 30 | issue = 2 | pages = 123–35 | date = August 1994 | pmid = 7816741 | doi = 10.1016/1043-6618(94)80004-9 }}{{cite journal | vauthors = Hung CR | title = Protective effects of lysozyme chloride and reduced glutathione on betel quid chewing-produced gastric oxidative stress and haemorrhagic ulcer in rats | journal = Inflammopharmacology | volume = 12 | issue = 2 | pages = 115–29 | date = May 2004 | pmid = 15265315 | doi = 10.1163/1568560041352284 | s2cid = 860321 }} The medical characteristics of this drug, and other phenylalkylamines, depends greatly on the state of the calcium channels being targeted which results in a greater affinity and drug efficiency. {{cite journal | vauthors = Cheng RC, Tikhonov DB, Zhorov BS | title = Structural model for phenylalkylamine binding to L-type calcium channels | journal = The Journal of Biological Chemistry | volume = 284 | issue = 41 | pages = 28332–42 | date = October 2009 | pmid = 19700404 | pmc = 2788883 | doi = 10.1074/jbc.M109.027326 | doi-access = free }}
References
{{Reflist}}
{{Calcium channel blockers}}
Category:Calcium channel blockers