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L4762

Loperamide hydrochloride

Name: Loperamide hydrochloride
Brand: SIGMA

98-102% (USP), powder, Ca2+ channel blocker

Synonym(s):

4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutyramide hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₃ClN₂O₂ · HCl

CAS Number:

34552-83-5

Molecular Weight:

513.50

NACRES:

NA.77

PubChem Substance ID:

24278042

UNSPSC Code:

12352200

EC Number:

252-082-4

MDL number:

MFCD00058581

Quality level:

200

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Properties

Product Name

Loperamide hydrochloride,

Quality Level

200

originator

Johnson & Johnson

SMILES string

Cl.CN(C)C(=O)C(CCN1CCC(O)(CC1)c2ccc(Cl)cc2)(c3ccccc3)c4ccccc4

InChI

1S/C29H33ClN2O2.ClH/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;1H

InChI key

PGYPOBZJRVSMDS-UHFFFAOYSA-N

Gene Information

human ... OPRM1(4988)

Description

Application

Loperamide hydrochloride (HCl) has been used in inflammatory pain experiments and to assess the functionality of proteins. 54

Biochem/physiol Actions

Loperamide hydrochloride (HCl) is a non-selective Ca²⁺ channel blocker. At nanomolar concentrations, it binds to μ-opioid receptors. Loperamide HCl does not cross the blood-brain barrier.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Slightly soluble in water and dilute acids, freely soluble in methanol and in chloroform, soluble in ethanol (95%).

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pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P264 - P270 - P301 + P310 + P330 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Articles

Using Human iPS Cell-derived Colon Organoids for Cytotoxicity Screening of Drug Compounds

Human epithelial intestinal colonic organoids can be used as an alternative to Caco-2 drug permeability assays for drug screening and compound toxicity testing.

Discover Bioactive Small Molecules for ADME/Tox

Loperamide blocks high-voltage-activated calcium channels and N-methyl-D-aspartate-evoked responses in rat and mouse cultured hippocampal pyramidal neurons.

J Church et al.

Molecular pharmacology, 45(4), 747-757 (1994-04-01)

The effects of the antidiarrheal agent loperamide on high-voltage-activated (HVA) calcium channel activity and excitatory amino acid-evoked responses in two preparations of cultured hippocampal pyramidal neurons were examined. In rat hippocampal neurons loaded with the calcium-sensitive dye fura-2, rises in

Mu opioid receptors on primary afferent nav1.8 neurons contribute to opiate-induced analgesia: insight from conditional knockout mice.

Raphaël Weibel et al.

PloS one, 8(9), e74706-e74706 (2013-09-27)

Opiates are powerful drugs to treat severe pain, and act via mu opioid receptors distributed throughout the nervous system. Their clinical use is hampered by centrally-mediated adverse effects, including nausea or respiratory depression. Here we used a genetic approach to

Loperamide (ADL 2-1294), an opioid antihyperalgesic agent with peripheral selectivity.

D L DeHaven-Hudkins et al.

The Journal of pharmacology and experimental therapeutics, 289(1), 494-502 (1999-03-23)

The antihyperalgesic properties of the opiate antidiarrheal agent loperamide (ADL 2-1294) were investigated in a variety of inflammatory pain models in rodents. Loperamide exhibited potent affinity and selectivity for the cloned micro (Ki = 3 nM) compared with the delta

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Global Trade Item Number

SKU	GTIN
L4762-25G	04061835546114
L4762-5G	04061833957714