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]
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
CHEBI:34772
CAS Number
16662-47-8
DrugBank ID
DB12923
TTD ID
D00ERV
VARIDT ID
DR00892
INTEDE ID
DR0762
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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.