From Wikipedia, the free encyclopedia
Devapamil
Names
IUPAC name
(RS )-2-(3,4-dimethoxyphenyl)-2-isopropyl-5-[2-(3-methoxyphenyl)ethyl-methylamino]pentanenitrile
Identifiers
ChEBI
ChEMBL
ChemSpider
UNII
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
Key: VMVKIDPOEOLUFS-UHFFFAOYAV
N#CC(c1cc(OC)c(OC)cc1)(CCCN(CCc2cccc(OC)c2)C)C(C)C
Properties
C26 H36 N2 O3
Molar mass
424.57564
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Devapamil is a
calcium channel blocker . It is also known as desmethoxyverapamil, which is a phenylalkylamine (PAA) derivative.
[1] Devapamil not only inhibits by blocking the calcium gated channels, but also by depolarizing the membrane during the sodium-potassium exchanges.
[2]
Structure
Devapamil consists of two aromatic rings with methoxy substituents connected by an alkylamine chain increasing flexibility and overall potency.
[3]
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.
[4]
[5] 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.
[6]
References
^ Erdmann R, Lüttgau HC (June 1989).
"The effect of the phenylalkylamine D888 (devapamil) on force and Ca2+ current in isolated frog skeletal muscle fibres" . The Journal of Physiology . 413 (1): 521–41.
doi :
10.1113/jphysiol.1989.sp017667 .
PMC
1189114 .
PMID
2557440 .
^ Dierkes PW, Wende V, Hochstrate P, Schlue WR (July 2004). "L-type Ca2+ channel antagonists block voltage-dependent Ca2+ channels in identified leech neurons". Brain Research . 1013 (2): 159–67.
doi :
10.1016/j.brainres.2004.03.038 .
PMID
15193524 .
S2CID
22004238 .
^ Cheng RC, Tikhonov DB, Zhorov BS (October 2009).
"Structural model for phenylalkylamine binding to L-type calcium channels" . The Journal of Biological Chemistry . 284 (41): 28332–42.
doi :
10.1074/jbc.M109.027326 .
PMC
2788883 .
PMID
19700404 .
^ Alican I, Toker F, Arbak S, Yegen BC, Yalçin AS, Oktay S (August 1994). "Gastric lipid peroxidation, glutathione and calcium channel blockers in the stress-induced ulcer model in rats". Pharmacological Research . 30 (2): 123–35.
doi :
10.1016/1043-6618(94)80004-9 .
PMID
7816741 .
^ Hung CR (May 2004). "Protective effects of lysozyme chloride and reduced glutathione on betel quid chewing-produced gastric oxidative stress and haemorrhagic ulcer in rats". Inflammopharmacology . 12 (2): 115–29.
doi :
10.1163/1568560041352284 .
PMID
15265315 .
S2CID
860321 .
^ Cheng RC, Tikhonov DB, Zhorov BS (October 2009).
"Structural model for phenylalkylamine binding to L-type calcium channels" . The Journal of Biological Chemistry . 284 (41): 28332–42.
doi :
10.1074/jbc.M109.027326 .
PMC
2788883 .
PMID
19700404 .
Calcium
VDCCs Tooltip Voltage-dependent calcium channels
Potassium
VGKCs Tooltip Voltage-gated potassium channels
IRKs Tooltip Inwardly rectifying potassium channel
KCa Tooltip Calcium-activated potassium channel
K2Ps Tooltip Tandem pore domain potassium channel
Sodium
VGSCs Tooltip Voltage-gated sodium channels
ENaC Tooltip Epithelial sodium channel
ASICs Tooltip Acid-sensing ion channel
Chloride
CaCCs Tooltip Calcium-activated chloride channel
CFTR Tooltip Cystic fibrosis transmembrane conductance regulator
Unsorted
Others
TRPs Tooltip Transient receptor potential channels
LGICs Tooltip Ligand gated ion channels