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L4762

Loperamide hydrochloride

Name: Loperamide hydrochloride
Brand: SIGMA

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

EC Number:

252-082-4

MDL number:

MFCD00058581

UNSPSC Code:

12352200

PubChem Substance ID:

24278042

NACRES:

NA.77

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)

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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%).

Pictograms

GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

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

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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

The DH31/CGRP enteroendocrine peptide triggers intestinal contractions favoring the elimination of opportunistic bacteria.

Olivia Benguettat et al.

PLoS pathogens, 14(9), e1007279-e1007279 (2018-09-05)

The digestive tract is the first organ affected by the ingestion of foodborne bacteria. While commensal bacteria become resident, opportunistic or virulent bacteria are eliminated from the gut by the local innate immune system. Here we characterize a new mechanism

An inhibitor-mediated beta-cell dedifferentiation model reveals distinct roles for FoxO1 in glucagon repression and insulin maturation.

Tamara Casteels et al.

Molecular metabolism, 54, 101329-101329 (2021-08-29)

The loss of forkhead box protein O1 (FoxO1) signaling in response to metabolic stress contributes to the etiology of type II diabetes, causing the dedifferentiation of pancreatic beta cells to a cell type reminiscent of endocrine progenitors. Lack of methods

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