GALLOPAMIL HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C28H40N2O5.ClH
Molecular Weight	521.089
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OKCRIUNHEQSXFD-UHFFFAOYSA-N

InChI=1S/C28H40N2O5.ClH/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;1H

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	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Involvement of ion channels in the induction of proenkephalin A gene expression by nicotine and cAMP in bovine chromaffin cells.	1987 Mar 25	2435729
[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
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites.	2000 Apr	10783826
Calcium transients in subcompartments of the leech Retzius neuron as induced by single action potentials.	2001 Jul	11391646
Left-to-right gradient of atrial frequencies during acute atrial fibrillation in the isolated sheep heart.	2001 May 29	11382735
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
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
Characteristics of sperm motility induced on the egg-jelly in the internal fertilization of the newt, Cynops pyrrhogaster.	2003 Mar	12692394
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
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
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
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
Ca2+ pathway involved in the refilling of store sites in rat adrenal medullary cells.	2009 Apr	19176761
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 15:12:47 GMT 2023` Edited by `admin` on `Fri Dec 15 15:12:47 GMT 2023`
Record UNII	VT4VR32A0T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GALLOPAMIL HYDROCHLORIDE

Common Name

English

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

Systematic Name

English

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

Common Name

English

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

Systematic Name

English

GALLOPAMIL HCL

Common Name

English

NSC-274966

Code

English

D-600 HYDROCHLORIDE

Code

English

Gallopamil hydrochloride [WHO-DD]

Common Name

English

PROCORUM

Brand Name

English

GALLOPAMIL HYDROCHLORIDE [MI]

Common Name

English

GALLOPAMIL HYDROCHLORIDE [MART.]

Common Name

English

ALGOCOR

Brand Name

English

GALLOPAMIL HYDROCHLORIDE [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C333