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Gallopamil

From Wikipedia, the free encyclopedia
Calcium channel blocker drug

Pharmaceutical compound
Gallopamil
Clinical data
Other namesMethoxyverapamil
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (RS)-5-[2-(3,4-Dimethoxyphenyl)ethyl-methylamino]-2-propan-2-yl-2-(3,4,5-trimethoxyphenyl)pentanenitrile
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC28H40N2O5
Molar mass484.637 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • N#CC(c1cc(OC)c(OC)c(OC)c1)(CCCN(CCc2ccc(OC)c(OC)c2)C)C(C)C
  • InChI=1S/C28H40N2O5/c1-20(2)28(19-29,22-17-25(33-6)27(35-8)26(18-22)34-7)13-9-14-30(3)15-12-21-10-11-23(31-4)24(16-21)32-5/h10-11,16-18,20H,9,12-15H2,1-8H3 checkY
  • Key:XQLWNAFCTODIRK-UHFFFAOYSA-N checkY

Gallopamil (INN) is an L-typecalcium channel blocker that is an analog ofverapamil. It is used in the treatment ofabnormal heart rhythms.[1]

Synthesis

[edit]

Thealkylation reaction of 3,4,5-trimethoxyphenylacetonitrile (1) andisopropyl chloride (2), usingsodium amide as base gives the intermediatenitrile (3). A second alkylation with a specificalkyl chloride (4) yields gallopamil.[2][3][4]

References

[edit]
  1. ^Sewing KF, Hannemann H (1983)."Calcium channel antagonists verapamil and gallopamil are powerful inhibitors of acid secretion in isolated and enriched guinea pig parietal cells".Pharmacology.27 (1):9–14.doi:10.1159/000137824.PMID 6310646.
  2. ^US patent 4115432, Dengel, Ferdinand, "Method for making basically-substituted phenylacetonitriles", issued 1978-09-19, assigned to Knoll GmbH 
  3. ^Theodore LJ, Nelson WL (1987). "Stereospecific synthesis of the enantiomers of verapamil and gallopamil".The Journal of Organic Chemistry.52 (7):1309–1315.doi:10.1021/jo00383a026.
  4. ^"Gallopamil". Thieme. Archived fromthe original on 2024-06-25. Retrieved2024-07-02.
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
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