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

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
[Anti-angina effect of gallopamil in comparison with another calcium antagonist and a placebo].	1984 Sep	6391005
Synthesis and release of luteinizing hormone in vitro by rat anterior pituitary cells: effects of gallopamil hydrochloride (D600) and pimozide.	1985 Oct	3896764
A comparison of nine calcium ion antagonists and propranolol: exercise tolerance, heart rate and ST-segment changes in patients with chronic stable angina pectoris.	1987	3653222
Involvement of ion channels in the induction of proenkephalin A gene expression by nicotine and cAMP in bovine chromaffin cells.	1987 Mar 25	2435729
Beta-adrenergic agonists stimulate the oxidative pentose phosphate pathway in the rat heart.	1990 Dec	1978808
Mechanisms involved in the transcriptional activation of proenkephalin gene expression in bovine chromaffin cells.	1990 Nov 5	2229066
[Drug treatment of myocardial ischemia].	1991	1686696
Effects of gallopamil, a Ca2+ channel blocker in models of ventricular arrhythmia in dogs.	1993 Feb 16	8449229
Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4.	2001 Dec	11743742
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
On the role of Ca(2+)- and voltage-dependent inactivation in Ca(v)1.2 sensitivity for the phenylalkylamine (-)gallopamil.	2001 Oct 12	11597993
A large sustained Ca2+ elevation occurs in unstimulated spines during the LTP pairing protocol but does not change synaptic strength.	2002	12440581
An increase in extracellular Ca(2+) concentration induces pigment aggregation in teleostean melanophores.	2002 Aug	12193799
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
Two types of ventricular fibrillation in isolated rabbit hearts: importance of excitability and action potential duration restitution.	2002 Oct 1	12356642
Verapamil drug metabolism studies by automated in-tube solid phase microextraction.	2002 Sep 5	12191717
Force response to stretches in activated frog muscle fibres at low tension.	2003	15098689
Demonstration of direct bioanalysis of drugs in plasma using nanoelectrospray infusion from a silicon chip coupled with tandem mass spectrometry.	2003 Feb 15	12622370
Characteristics of sperm motility induced on the egg-jelly in the internal fertilization of the newt, Cynops pyrrhogaster.	2003 Mar	12692394
A tale of two fibrillations.	2003 Nov 11	14609997
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
Opposite effects of a single IIIS5 mutation on phenylalkylamine and dihydropyridine interaction with L-type Ca2+ channels.	2004 Dec 31	15504730
Changes in calcium signalling, gravitropism, and statocyte ultrastructure in pea roots induced by calcium channel blockers.	2004 Jul	16240511
L-type Ca2+ channel antagonists block voltage-dependent Ca2+ channels in identified leech neurons.	2004 Jul 9	15193524
Non-cross-bridge calcium-dependent stiffness in frog muscle fibers.	2004 Jun	14749216
NMDA receptor-mediated depolarizing after-potentials in the basal dendrites of CA1 pyramidal neurons.	2004 Mar	15154678
Multidimensional on-line sample preparation of verapamil and its metabolites by a molecularly imprinted polymer coupled to liquid chromatography-mass spectrometry.	2004 Mar 5	14751799
Mechanisms intrinsic to 5-HT2B receptor-induced potentiation of NMDA receptor responses in frog motoneurones.	2004 Oct	15339859
Mother rotors and the mechanisms of D600-induced type 2 ventricular fibrillation.	2004 Oct 12	15466637
Pharmacophoric features and Ca2+ ion holding capacity of verapamil.	2005 Dec 15	16213727
An ionic model for rhythmic activity in small clusters of embryonic chick ventricular cells.	2005 Jul	15708964
Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect.	2005 Jun	15806115
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
A selective beta2-adrenergic agonist, terbutaline, improves sepsis-induced diaphragmatic dysfunction in the rat.	2006 Jul 24	16603198
Airway smooth muscle as a target of asthma therapy: history and new directions.	2006 Sep 29	17010205
Influence of model melanoidins on calcium-dependent transport mechanisms in smooth muscle tissue.	2007 Apr	17357983
Persistent (>24h) long-term depression in the dentate gyrus of freely moving rats is not dependent on activation of NMDA receptors, L-type voltage-gated calcium channels or protein synthesis.	2007 Jan	16899259
Endogenous alkaline transients boost postsynaptic NMDA receptor responses in hippocampal CA1 pyramidal neurons.	2007 Jul 11	17626204
Effects of phenylalkylamines and benzothiazepines on Ca(v)1.3-mediated Ca2+ currents in neonatal mouse inner hair cells.	2007 Nov 14	17651721
Formation of DNA-damaging N-nitroso compounds from the interaction of calcium-channel blockers with nitrite.	2007 Sep 5	17644234
Mechanisms of potassium- and capsaicin-induced axonal calcitonin gene-related peptide release: involvement of L- and T-type calcium channels and TRPV1 but not sodium channels.	2008 Feb 6	18178321
Positive inotropic effects of epigallocatechin-3-gallate (EGCG) involve activation of Na+/H+ and Na+/Ca2+ exchangers.	2008 May	18406205
Ca2+ pathway involved in the refilling of store sites in rat adrenal medullary cells.	2009 Apr	19176761
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
Reduction in extracellular Ca2+ attenuates endothelium-dependent relaxation more than nitroprusside-induced relaxation.	2010 Jan	19915583

Patents

Sample Use Guides

In Vivo Use Guide

150 mg/day

Route of Administration: Oral

In Vitro Use Guide

Unknown

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