Devapamil

Devapamil
Names
	IUPAC name (RS)-2-(3,4-dimethoxyphenyl)-2-isopropyl-5-[2-(3-methoxyphenyl)ethyl-methylamino]pentanenitrile
Identifiers
CAS Number	92302-55-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34673 ;
ChEMBL	ChEMBL2074792;
ChemSpider	59244;
PubChem CID	65832;
UNII	M6142PTV7J ;
CompTox Dashboard (EPA)	DTXSID60869094 ;
	InChI 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;
	SMILES N#CC(c1cc(OC)c(OC)cc1)(CCCN(CCc2cccc(OC)c2)C)C(C)C;
Properties
Chemical formula	C26H36N2O3
Molar mass	424.585 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.

[1] 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.

[2] 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.

[3] 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.

[4] 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.

[5] 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.

[6] 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.

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Devapamil

Structure

Animal studies

References

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