LOPERAMIDE

Search structure
Synonyms:
Status: Approved (1976)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A07DA03
UNII: 6X9OC3H4II

Structure
InChI Key RDOIQAHITMMDAJ-UHFFFAOYSA-N
Smile 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

Pharmacology

Primary Target
μ receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 2000 - - -
Enzyme Hydrolase
- 4060-6800 - 1500 -0.8982-20.6
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase MSN subfamily
- - - - 17-65
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Tie family
- - 5900 - -
Enzyme Transferase
- - - - 17.59
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -10.91--2.16
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 33 - - 17-65
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 239 - - 100
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Opioid receptor
156 1.445 - 0.268-0.586 -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Somatostatin receptor
- 33110 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 3005 - 2066 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- 1337 - 454-1940 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 3081 - 3030 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- 4105 - 2613 -
Membrane receptor
156 1337 - 0.268-0.586 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 2202 - 1170 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 19.6
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 23700 - - 73.4
Transporter Electrochemical transporter
- 2202 - 1170 19.6
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 2500 - - 4.5
Unclassified protein
- 12000 3500 - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Diarrhea 3 D003967 ClinicalTrials
Fecal Incontinence 3 D005242 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Clostridium Infections 2 D003015 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Paget Disease, Extramammary 2 D010145 ClinicalTrials
Eczema 2 D004485 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Pain 1 D010146 ClinicalTrials
Intestinal Obstruction 1 D007415 ClinicalTrials

Related Entries

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 53179-11-6
ChEBI 6532
ChEMBL CHEMBL841
DrugBank DB00836
DrugCentral 1599
EPA CompTox DTXSID6045165
FDA SRS 6X9OC3H4II
Human Metabolome Database HMDB04999
Guide to Pharmacology 7215
KEGG C07080
PharmGKB PA450262
PubChem 3955
SureChEMBL SCHEMBL28530
ZINC ZINC000000537928
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