U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of GALLOPAMIL

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 ( + / - )

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

Targets

Primary TargetPharmacologyConditionPotency
5.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROCORUM

Approved Use

Unknown
Primary
PROCORUM

Approved Use

Unknown
Primary
PROCORUM

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Mechanisms involved in the transcriptional activation of proenkephalin gene expression in bovine chromaffin cells.
1990 Nov 5
Left-to-right gradient of atrial frequencies during acute atrial fibrillation in the isolated sheep heart.
2001 May 29
Initial and sustained phases of myogenic response of rat mesenteric small arteries.
2001 Nov
On the role of Ca(2+)- and voltage-dependent inactivation in Ca(v)1.2 sensitivity for the phenylalkylamine (-)gallopamil.
2001 Oct 12
Two types of ventricular fibrillation in isolated rabbit hearts: importance of excitability and action potential duration restitution.
2002 Oct 1
Verapamil drug metabolism studies by automated in-tube solid phase microextraction.
2002 Sep 5
Changes in calcium signalling, gravitropism, and statocyte ultrastructure in pea roots induced by calcium channel blockers.
2004 Jul
Non-cross-bridge calcium-dependent stiffness in frog muscle fibers.
2004 Jun
NMDA receptor-mediated depolarizing after-potentials in the basal dendrites of CA1 pyramidal neurons.
2004 Mar
Mechanisms intrinsic to 5-HT2B receptor-induced potentiation of NMDA receptor responses in frog motoneurones.
2004 Oct
Insulin stimulates Ca2+ uptake via PKC, cAMP, and p38 MAPK in mouse embryonic stem cells.
2005 May 6
Formation of DNA-damaging N-nitroso compounds from the interaction of calcium-channel blockers with nitrite.
2007 Sep 5
Ca2+ pathway involved in the refilling of store sites in rat adrenal medullary cells.
2009 Apr
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
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
  • Download
Name Type Language
GALLOPAMIL
INN   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
NCI_THESAURUS C333
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
WHO-VATC QC08DA02
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1275
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
PUBCHEM
1234
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
WIKIPEDIA
GALLOPAMIL
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
ChEMBL
CHEMBL51149
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID5045172
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
CAS
16662-47-8
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
CAS
56949-78-1
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
SUPERSEDED
SMS_ID
100000084512
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
DRUG BANK
DB12923
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
NCI_THESAURUS
C83725
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
EVMPD
SUB07874MIG
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
INN
4318
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
RXCUI
4648
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY RxNorm
MESH
D005711
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
MERCK INDEX
m5656
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY Merck Index
FDA UNII
39WPC8JHR8
Created by admin on Fri Dec 15 16:52:37 GMT 2023 , Edited by admin on Fri Dec 15 16:52:37 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
BINDING
IC50
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY