GALLOPAMIL

Details

Stereochemistry	RACEMIC
Molecular Formula	C28H40N2O5
Molecular Weight	484.6276
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(=CC(OC)=C1OC)C(CCCN(C)CCC2=CC(OC)=C(OC)C=C2)(C#N)C(C)C

InChI

InChIKey=XQLWNAFCTODIRK-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C28H40N2O5
Molecular Weight	484.6276
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7510624

Gallopamil is a L-type calcium channel blocker designed for the treatment of coronary heart diseases: angina pectoris, prinzmetal angina and hypertonia.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7510624	Blocker 537		5.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Angina pectoris 106 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9197430	Primary	Approved 8429	PROCORUM Approved Use Unknown
Prinzmetal angina 2 Sources: http://www.pharmazie.com/graphic/A/30/1-18830.pdf	Primary	Approved 8429	PROCORUM Approved Use Unknown
Hypertension 567 Sources: http://www.pharmazie.com/graphic/A/30/1-18830.pdf	Primary	Approved 8429	PROCORUM Approved Use Unknown

PubMed

Title	Date	PubMed
The effect of a calcium antagonist (D600) on isoprenaline-induced myocardial necrosis in the rat.	1979 Jun	475980
[Drug treatment of myocardial ischemia].	1991	1686696
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites.	2000 Apr	10783826
Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4.	2001 Dec	11743742
Determination of fendiline and gallopamil by capillary isotachophoresis.	2001 Jun 15	11417865
Left-to-right gradient of atrial frequencies during acute atrial fibrillation in the isolated sheep heart.	2001 May 29	11382735
Initial and sustained phases of myogenic response of rat mesenteric small arteries.	2001 Nov	11668080
Intracellular and extracellular calcium utilization during hypoxic vasoconstriction of cyclostome aortas.	2001 Nov	11641122
A randomized prospective double-blind placebo-controlled study of gallopamil, calcium antagonist of the verapamil type, in stable cyclosporine-treated renal transplant recipients.	2002 Aug	12176568
Demonstration of direct bioanalysis of drugs in plasma using nanoelectrospray infusion from a silicon chip coupled with tandem mass spectrometry.	2003 Feb 15	12622370
Role of sarcoplasmic reticulum Ca2+ content in Ca2+ entry of bovine airway smooth muscle cells.	2003 Oct	14504687
[L-type calcium channels involvement in aortic smooth muscle contraction as revealed by membrane potential and active force dynamics].	2004 Apr-Jun	15688830
Changes in calcium signalling, gravitropism, and statocyte ultrastructure in pea roots induced by calcium channel blockers.	2004 Jul	16240511
NMDA receptor-mediated depolarizing after-potentials in the basal dendrites of CA1 pyramidal neurons.	2004 Mar	15154678
Pharmacophoric features and Ca2+ ion holding capacity of verapamil.	2005 Dec 15	16213727
Insulin stimulates Ca2+ uptake via PKC, cAMP, and p38 MAPK in mouse embryonic stem cells.	2005 May 6	15820502
Nitric oxide involvement in pancreatic beta cell apoptosis by glibenclamide.	2006 Feb	16256381
Formation of DNA-damaging N-nitroso compounds from the interaction of calcium-channel blockers with nitrite.	2007 Sep 5	17644234
Structural model for phenylalkylamine binding to L-type calcium channels.	2009 Oct 9	19700404
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443

Patents

Sample Use Guides

In Vivo Use Guide

150 mg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:52:36 GMT 2023` Edited by `admin` on `Fri Dec 15 16:52:36 GMT 2023`
Record UNII	39WPC8JHR8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GALLOPAMIL

Official Name

English

DL-D-600

Code

English

gallopamil [INN]

Common Name

English

.ALPHA.-(3-((2-(3,4-DIMETHOXYPHENYL)ETHYL)METHYLAMINO)PROPYL)-3,4,5-TRIMETHOXY-.ALPHA.-(1-METHYLETHYL)BENZENEACETONITRILE

Systematic Name

English

LU-30-029

Code

English

5-((3,4-DIMETHOXYPHENETHYL)METHYLAMINO)-2-ISOPROPYL-2-(3,4,5-TRIMETHOXYPHENYL)VALERONITRILE

Systematic Name

English

GALLOPAMIL [MI]

Common Name

English

.ALPHA.-ISOPROPYL-.ALPHA.-((N-METHYL-N-HOMOVERATRYL)-.GAMMA.-AMINOPROPYL)-3,4,5-TRIMETHOXYPHENYLACETONITRILE

Common Name

English

D-600

Code

English

METHOXYVERAPAMIL

Common Name

English

(±)-Methoxyverapamil

Common Name

English

Gallopamil [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C08DA02