Details of the Drug

General Information of Drug (ID: DMXBR27)

Drug Name
Gallopamil
Synonyms
16662-47-8; methoxyverapamil; 5-((3,4-Dimethoxyphenethyl)(methyl)amino)-2-isopropyl-2-(3,4,5-trimethoxyphenyl)pentanenitrile; Galopamilo; Galopamilo [INN-Spanish]; Gallopamillum [INN-Latin]; Gallopamil [INN:BAN]; D600; D 600; C28H40N2O5; CHEBI:34772; (+/-)-Methoxyverapamil hydrochloride; 5-[(3,4-Dimethoxyphenethyl)methylamino]-2-isopropyl-2-(3,4,5-trimethoxyphenyl)valeronitrile; Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4,5-trimethoxy-alpha-(1-methylethyl)-; Methoxyverapamil; GSK 796406
Indication
Disease Entry ICD 11 Status REF
Asthma CA23 Phase 2 [1]
Hypertension BA00-BA04 Discontinued in Phase 1 [2]
ATC Code
C08DA02: Gallopamil
C08DA: Phenylalkylamine derivatives
C08D: SELECTIVE CALCIUM CHANNEL BLOCKERS WITH DIRECT CARDIAC EFFECTS
C08: CALCIUM CHANNEL BLOCKERS
C: CARDIOVASCULAR SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 484.6
Logarithm of the Partition Coefficient (xlogp) 3.8
Rotatable Bond Count (rotbonds) 14
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 14.3 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.8 hours [3]
Unbound Fraction
The unbound fraction of drug in plasma is 0.07% [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.75 L/kg [3]
Chemical Identifiers
Formula
C28H40N2O5
IUPAC Name
5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-yl-2-(3,4,5-trimethoxyphenyl)pentanenitrile
Canonical SMILES
CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C(=C2)OC)OC)OC
InChI
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
InChIKey
XQLWNAFCTODIRK-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
1234
ChEBI ID
CHEMBL51149
CAS Number
16662-47-8
UNII
39WPC8JHR8
DrugBank ID
DB12923
TTD ID
D00ERV
VARIDT ID
DR00892
INTEDE ID
DR0762
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Angiotensin-converting enzyme (ACE) TTL69WB ACE_HUMAN Inhibitor [4]
Neutral endopeptidase (MME) TT5TKPM NEP_HUMAN Inhibitor [4]
Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 (ATP2A2) TTE6THL AT2A2_HUMAN Inhibitor [5]
Voltage-gated L-type calcium channel (L-CaC) TTXHYV6 NOUNIPROTAC Blocker [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [8]
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Molecular Expression Atlas of This Drug

The Studied Disease Asthma
ICD Disease Classification CA23
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Angiotensin-converting enzyme (ACE) DTT SLC33A1 2.62E-01 -0.01 -0.06
P-glycoprotein 1 (ABCB1) DTP P-GP 7.83E-01 4.69E-02 1.89E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 6.06E-01 -2.42E-02 -1.64E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00896428) Effects of Gallopamil in Severe Asthma (REMODEL'ASTHME) in University Hospital, Bordeaux.
2 Mechanism of Vasopeptidase Inhibitor-Induced Plasma Extravasation: Comparison of Omapatrilat and the Novel Neutral Endopeptidase 24.11/Angiotensin-Converting Enzyme Inhibitor GW796406. JPET December 2005 vol. 315 no. 3 1306-1313.
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Mechanism of vasopeptidase inhibitor-induced plasma extravasation: comparison of omapatrilat and the novel neutral endopeptidase 24.11/angiotensin-converting enzyme inhibitor GW796406. J Pharmacol Exp Ther. 2005 Dec;315(3):1306-13.
5 Interaction of D-600 with the transmembrane domain of the sarcoplasmic reticulum Ca(2+)-ATPase. Am J Physiol Cell Physiol. 2000 Jul;279(1):C166-72.
6 Role of apoptosis in the kidney after reperfusion. Orv Hetil. 2008 Feb 17;149(7):305-15.
7 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
8 Identification of human cytochrome P-450 isoforms involved in metabolism of R(+)- and S(-)-gallopamil: utility of in vitro disappearance rate. Drug Metab Dispos. 1999 Nov;27(11):1254-9.