Structure via PubChem · Public domain (PubChem)
devapamil
Sign in to saveAlso known as 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-((m-methoxyphenethyl)methylamino)valeronitrile, 5-(N-(3-methoxyphenethyl)-N-methylamino)-2-isopropyl-2-(3,4-dimethoxyphenyl)pentanenitrile
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.
Chemical data
- Formula
- C26H36N2O3
- Molecular weight
- 424.6 g/mol
- IUPAC name
- 2-(3,4-dimethoxyphenyl)-5-[2-(3-methoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
- SMILES
- CC(C)C(CCCN(C)CCC1=CC(=CC=C1)OC)(C#N)C2=CC(=C(C=C2)OC)OC
- InChIKey
- VMVKIDPOEOLUFS-UHFFFAOYSA-N
- XLogP
- 3.8
- Polar surface area
- 54.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
35 papers- The devapamil-binding site of the purified skeletal muscle receptor for organic-calcium channel blockers is modulated by micromolar and millimolar concentrations of Ca2+.European journal of biochemistry · 1991
- The effect of the phenylalkylamine D888 (devapamil) on force and Ca2+ current in isolated frog skeletal muscle fibres.The Journal of physiology · 1989
- Calcium channel block by (-)devapamil is affected by the sequence environment and composition of the phenylalkylamine receptor site.Biophysical journal · 1997
- Structural model for phenylalkylamine binding to L-type calcium channels.The Journal of biological chemistry · 2009
- Extra- and intracellular action of quaternary devapamil on muscle L-type Ca(2+)-channels.British journal of pharmacology · 1996
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 424.273
Show 4 more facts
- chemical formula
- C₂₆H₃₆N₂O₃
- canonical SMILES
- CC(C)C(CCCN(C)CCC1=CC(=CC=C1)OC)(C#N)C2=CC(=C(C=C2)OC)OC
- World Health Organisation international non-proprietary name
- devapamil
- subject has role
- calcium channel blocker
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Structure
- Animal studies
- References
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.
== Structure == Devapamil consists of two aromatic rings with methoxy substituents connected by an alkylamine chain increasing flexibility and overall potency.
Excerpted from Wikipedia’s “devapamil” article, available under the CC BY-SA 4.0 licence.