LOPERAMIDE

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Synonyms
Status
Molecule Category Free-form
ATC A07DA03
UNII 6X9OC3H4II
EPA CompTox DTXSID6045165

Structure

InChI Key RDOIQAHITMMDAJ-UHFFFAOYSA-N
Smiles CN(C)C(=O)C(CCN1CCC(O)(c2ccc(Cl)cc2)CC1)(c1ccccc1)c1ccccc1
InChI
InChI=1S/C29H33ClN2O2/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C29H33ClN2O2
Molecular Weight 477.05
AlogP 5.09
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 43.78
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 34.0
Assay Description Organism Bioactivity Reference
Percent inhibition of caster oil induced diarrhea in rats at a dose of 10 mg/kg peroral administration after 2 hours Rattus norvegicus 100.0 %
Percent inhibition of caster oil induced diarrhea in rats at a dose of 10 mg/kg peroral administration after 6 hours Rattus norvegicus 99.0 %
Percent inhibition of caster oil induced diarrhea in rats at a dose of 30 mg/kg peroral administration after 2 hours Rattus norvegicus 98.0 %
Percent inhibition of caster oil induced diarrhea in rats at a dose of 30 mg/kg peroral administration after 6 hours Rattus norvegicus 97.0 %
Percent inhibition of caster oil induced diarrhea in rats at a dose of 3 mg/kg peroral administration after 2 hr Rattus norvegicus 96.0 %
Percent inhibition of caster oil induced diarrhea in rats at a dose of 3 mg/kg peroral administration after 6 hr Rattus norvegicus 77.0 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex Cavia porcellus 270.0 nM
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 100.0 %
Binding affinity for Mu opioid receptor of rat brain Rattus norvegicus 0.16 nM
Binding affinity for delta opioid receptor of rat brain Rattus norvegicus 50.1 nM
Binding affinity for recombinant human mu-opioid receptor was determined by using [3H]- diprenophine radioligand Homo sapiens 0.53 nM
Inhibition of isolated guinea pig ileum contraction induced by electrical stimulation Cavia porcellus 488.9 nM
Inhibition of mu opioid receptor mediated GTPgammaS binding to CHO cell membranes Cavia porcellus 58.0 nM
Inhibition of delta opioid receptor mediated GTPgammaS binding to CHO cell membranes None 156.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 73.4 %
DRUGMATRIX: Opiate delta1 (OP1, DOP) radioligand binding (ligand: [3H] Naltrindole) None 896.0 nM DRUGMATRIX: Opiate delta1 (OP1, DOP) radioligand binding (ligand: [3H] Naltrindole) None 316.0 nM
DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine) None 1.445 nM DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine) None 0.586 nM
DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 965.0 nM DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) Rattus norvegicus 534.0 nM
DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 221.0 nM DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand: [3H] Diltiazem) Rattus norvegicus 196.0 nM
DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 628.0 nM DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 264.0 nM
DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) Rattus norvegicus 848.0 nM
DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotoxin) Rattus norvegicus 93.0 nM DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotoxin) Rattus norvegicus 85.0 nM
DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 589.0 nM DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand: [3H] (-)-Desmethoxyverapamil (D-888)) Rattus norvegicus 573.0 nM
DRUGMATRIX: Dopamine D3 radioligand binding (ligand: [3H] Spiperone) None 454.0 nM
Inhibition of norA-mediated ethidium bromide efflux in Staphylococcus aureus SA-1199B harboring grlA A116E mutant at 50 uM after 5 mins by fluorometric analysis Staphylococcus aureus 77.7 %
Inhibition of human recombinant MDR1 expressed in mouse L5178Y cells assessed as inhibition of rhodamine-123 efflux at 10'-5 M preincubated for 10 mins measured after 20 mins by FACS analysis Homo sapiens 4.5 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 32.5 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 32.4 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 19.6 %
Inhibition of human KvLQT1/minK channel expressed in CHO cells at 1 uM at holding potential of -80 mV by whole cell patch clamp assay relative to control Homo sapiens 17.0 %
Inhibition of human KvLQT1/minK channel expressed in CHO cells at 10 uM at holding potential of -80 mV by whole cell patch clamp assay relative to control Homo sapiens 65.0 %
Inhibition of human Nav1.5 channel expressed in HEK293 cells at holding potential of -70 mV by whole cell patch clamp assay Homo sapiens 239.0 nM
Inhibition of human ERG expressed in HEK293 cells at holding potential of -80 mV by whole cell patch clamp assay Homo sapiens 33.0 nM
Inhibition of human ERG expressed in HEK293 cells by patch clamp assay Homo sapiens 20.0 %
Inhibition of CRT CVIET haplotype mutant in Plasmodium falciparum K1 isolate MRA-159 infected in erythrocytes assessed as reversal of chloroquine resistance by measuring reduction in chloroquine IC50 by Hoechst 33342 staining based flow cytometry Plasmodium falciparum K1 685.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 17.59 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 89.59 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 89.59 %
Displacement of [3H]DAMGO from human mu opioid receptor expressed in HEK293 cell membrane incubated for 60 mins by radioligand binding assay Homo sapiens 0.268 nM

Cross References

Resources Reference
ChEBI 6532
ChEMBL CHEMBL841
DrugBank DB00836
DrugCentral 1599
FDA SRS 6X9OC3H4II
Human Metabolome Database HMDB0004999
Guide to Pharmacology 7215
KEGG C07080
PharmGKB PA450262
PubChem 3955
SureChEMBL SCHEMBL28530
ZINC ZINC000000537928
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