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=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C(OC)=C2)C=C1OC

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 95 Target ID: CHEMBL2095229 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7510624	Blocker 555		5.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Angina pectoris 110 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9197430	Primary	Approved 8583	PROCORUM Approved Use Unknown
Prinzmetal angina 2 Sources: http://www.pharmazie.com/graphic/A/30/1-18830.pdf	Primary	Approved 8583	PROCORUM Approved Use Unknown
Hypertension 575 Sources: http://www.pharmazie.com/graphic/A/30/1-18830.pdf	Primary	Approved 8583	PROCORUM Approved Use Unknown

C_max

Value	Dose	Analyte	Population
117.8 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
96.4 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
36.8 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
50.9 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
249.1 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
61.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8981554/	80 mg 3 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	GALLOPAMIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
77 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8981554/	80 mg 3 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	GALLOPAMIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
196.9 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
187.8 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
79.5 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
111.9 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
574.8 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
206 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8981554/	80 mg 3 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	GALLOPAMIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
295.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8981554/	80 mg 3 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	GALLOPAMIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
4.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8981554/	80 mg 3 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	GALLOPAMIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8981554/	80 mg 3 times / day multiple, oral dose: 80 mg route of administration: Oral experiment type: MULTIPLE co-administered:	GALLOPAMIL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Analyte	Population
4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8398599/		GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status:
5.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8398599/		GALLOPAMIL, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
7.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3443143/		GALLOPAMIL serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.6% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9190842/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	GALLOPAMIL, (R)- serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1284163/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1284163/	Other AEs: Constipation... Other AEs: Constipation (2.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/1284163/
150 mg 3 times / day multiple, oral Studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6367415/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6367415/	Disc. AE: Unstable angina... Other AEs: Acute myocardial infarction... AEs leading to discontinuation/dose reduction: Unstable angina Other AEs: Acute myocardial infarction (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/6367415/

AEs

AE	Significance	Dose	Population
Constipation	2.5%	200 mg 2 times / day multiple, oral Highest studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1284163/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1284163/
Unstable angina	Disc. AE	150 mg 3 times / day multiple, oral Studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6367415/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6367415/
Acute myocardial infarction	grade 5	150 mg 3 times / day multiple, oral Studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6367415/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6367415/

PubMed

Title	Date	PubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
Reduction in extracellular Ca2+ attenuates endothelium-dependent relaxation more than nitroprusside-induced relaxation.	2010-01	19915583
Structural model for phenylalkylamine binding to L-type calcium channels.	2009-10-09	19700404
Ca2+ pathway involved in the refilling of store sites in rat adrenal medullary cells.	2009-04	19176761
Positive inotropic effects of epigallocatechin-3-gallate (EGCG) involve activation of Na+/H+ and Na+/Ca2+ exchangers.	2008-05	18406205
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.	2008-02-06	18178321
Effects of phenylalkylamines and benzothiazepines on Ca(v)1.3-mediated Ca2+ currents in neonatal mouse inner hair cells.	2007-11-14	17651721
Formation of DNA-damaging N-nitroso compounds from the interaction of calcium-channel blockers with nitrite.	2007-09-05	17644234
Endogenous alkaline transients boost postsynaptic NMDA receptor responses in hippocampal CA1 pyramidal neurons.	2007-07-11	17626204
Influence of model melanoidins on calcium-dependent transport mechanisms in smooth muscle tissue.	2007-04	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.	2007-01	16899259
Airway smooth muscle as a target of asthma therapy: history and new directions.	2006-09-29	17010205
A selective beta2-adrenergic agonist, terbutaline, improves sepsis-induced diaphragmatic dysfunction in the rat.	2006-07-24	16603198
Nitric oxide involvement in pancreatic beta cell apoptosis by glibenclamide.	2006-02	16256381
Pharmacophoric features and Ca2+ ion holding capacity of verapamil.	2005-12-15	16213727
An ionic model for rhythmic activity in small clusters of embryonic chick ventricular cells.	2005-07	15708964
Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect.	2005-06	15806115
Insulin stimulates Ca2+ uptake via PKC, cAMP, and p38 MAPK in mouse embryonic stem cells.	2005-05-06	15820502
[L-type calcium channels involvement in aortic smooth muscle contraction as revealed by membrane potential and active force dynamics].	2005-02-04	15688830
Opposite effects of a single IIIS5 mutation on phenylalkylamine and dihydropyridine interaction with L-type Ca2+ channels.	2004-12-31	15504730
Mother rotors and the mechanisms of D600-induced type 2 ventricular fibrillation.	2004-10-12	15466637
Mechanisms intrinsic to 5-HT2B receptor-induced potentiation of NMDA receptor responses in frog motoneurones.	2004-10	15339859
L-type Ca2+ channel antagonists block voltage-dependent Ca2+ channels in identified leech neurons.	2004-07-09	15193524
Changes in calcium signalling, gravitropism, and statocyte ultrastructure in pea roots induced by calcium channel blockers.	2004-07	16240511
Non-cross-bridge calcium-dependent stiffness in frog muscle fibers.	2004-06	14749216
Multidimensional on-line sample preparation of verapamil and its metabolites by a molecularly imprinted polymer coupled to liquid chromatography-mass spectrometry.	2004-03-05	14751799
NMDA receptor-mediated depolarizing after-potentials in the basal dendrites of CA1 pyramidal neurons.	2004-03	15154678
A tale of two fibrillations.	2003-11-11	14609997
Role of sarcoplasmic reticulum Ca2+ content in Ca2+ entry of bovine airway smooth muscle cells.	2003-10	14504687
Characteristics of sperm motility induced on the egg-jelly in the internal fertilization of the newt, Cynops pyrrhogaster.	2003-03	12692394
Demonstration of direct bioanalysis of drugs in plasma using nanoelectrospray infusion from a silicon chip coupled with tandem mass spectrometry.	2003-02-15	12622370
Force response to stretches in activated frog muscle fibres at low tension.	2003	15098689
Two types of ventricular fibrillation in isolated rabbit hearts: importance of excitability and action potential duration restitution.	2002-10-01	12356642
Verapamil drug metabolism studies by automated in-tube solid phase microextraction.	2002-09-05	12191717
An increase in extracellular Ca(2+) concentration induces pigment aggregation in teleostean melanophores.	2002-08	12193799
A randomized prospective double-blind placebo-controlled study of gallopamil, calcium antagonist of the verapamil type, in stable cyclosporine-treated renal transplant recipients.	2002-08	12176568
A large sustained Ca2+ elevation occurs in unstimulated spines during the LTP pairing protocol but does not change synaptic strength.	2002	12440581
Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4.	2001-12	11743742
Initial and sustained phases of myogenic response of rat mesenteric small arteries.	2001-11	11668080
Intracellular and extracellular calcium utilization during hypoxic vasoconstriction of cyclostome aortas.	2001-11	11641122
On the role of Ca(2+)- and voltage-dependent inactivation in Ca(v)1.2 sensitivity for the phenylalkylamine (-)gallopamil.	2001-10-12	11597993
Effects of gallopamil, a Ca2+ channel blocker in models of ventricular arrhythmia in dogs.	1993-02-16	8449229
[Drug treatment of myocardial ischemia].	1991	1686696
Beta-adrenergic agonists stimulate the oxidative pentose phosphate pathway in the rat heart.	1990-12	1978808
Mechanisms involved in the transcriptional activation of proenkephalin gene expression in bovine chromaffin cells.	1990-11-05	2229066
Involvement of ion channels in the induction of proenkephalin A gene expression by nicotine and cAMP in bovine chromaffin cells.	1987-03-25	2435729
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
Synthesis and release of luteinizing hormone in vitro by rat anterior pituitary cells: effects of gallopamil hydrochloride (D600) and pimozide.	1985-10	3896764
[Anti-angina effect of gallopamil in comparison with another calcium antagonist and a placebo].	1984-09	6391005
The effect of a calcium antagonist (D600) on isoprenaline-induced myocardial necrosis in the rat.	1979-06	475980

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 `Mon Mar 31 18:37:23 GMT 2025` Edited by `admin` on `Mon Mar 31 18:37:23 GMT 2025`
Record UNII	39WPC8JHR8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

D-600

Preferred Name

English

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

METHOXYVERAPAMIL

Common Name

English

(±)-Methoxyverapamil

Common Name

English

Gallopamil [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C08DA02