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5.08162

Sigma-Aldrich

Loperamide Hydrochloride

Synonym(e):

Loperamide Hydrochloride, µ-Opioid Receptor Agonist, Loperamide Hydrochloride, Imodium

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About This Item

Empirische Formel (Hill-System):
C29H33ClN2O2 · xHCl
CAS-Nummer:
34552-83-5
Molekulargewicht:
477.04 (free base basis)
MDL-Nummer:
MFCD00058581
UNSPSC-Code:
12352200
NACRES:
NA.77

Assay

≥99% (HPLC)

Qualitätsniveau

100

Form

solid

Wirksamkeit

2 nM Ki

Hersteller/Markenname

Calbiochem®

Lagerbedingungen

OK to freeze
protect from light

Farbe

white

Löslichkeit

DMSO: 50 mM
ethanol: 50 mM

Lagertemp.

2-8°C

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

InChIKey

PGYPOBZJRVSMDS-UHFFFAOYSA-N

Allgemeine Beschreibung

A very potent and highly selective peripheral resctricted µ-opioid receptor agonist (Ki = 2 nM). Often used as an antidiarrheal, antipruritic, and antihyperalgesic agent. In addition, shown to improve defective post-receptor insulin signaling in skeletal muscle cells and enhance insulin sensitivity in rats.

Biochem./physiol. Wirkung

Primary Target
u opioid receptor

Warnhinweis

Toxicity: Toxic (F)

Angaben zur Herstellung

Warming is required for complete solubilization in ethanol.

Rekonstituierung

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Sonstige Hinweise

Cheng, K., et al. 2013. Pharmaco. Ther.139, 334.
Di Bosco, M., et al. 2008. Chem. Biol. Drug Des.71, 328.
DeHaven-Hudkins, D., et al. 1999. J. Pharmacol. Exp. Ther.289, 494.
Mackerer, C., et al. 1976. J. Pharmacol. Exp. Ther.199, 131.
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Rechtliche Hinweise

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H301

Gefahreneinstufungen

Acute Tox. 3 Oral

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

Antonio Mazzella di Bosco et al.
Chemical biology & drug design, 71(4), 328-335 (2008-02-21)
Loperamide is a piperidine analogue, acting as agonist on peripheral opioid receptors, exhibiting affinity and selectivity for the cloned mu human opioid receptor compared with the delta human opioid receptor. Automatic docking studies of loperamide, using AutoDock, on human mu-
C R Mackerer et al.
The Journal of pharmacology and experimental therapeutics, 199(1), 131-140 (1976-10-01)
Loperamide, a new antidiarrheal agent, was tested to determine whether its biological activity involves binding to opiate receptor sites. Loperamide and morphine competitively inhibited 3H-naloxone binding to homogenates a guinea-pig brain and myenteric plexus. The Kp values obtain in the
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
Kai-Chun Cheng et al.
Pharmacology & therapeutics, 139(3), 334-340 (2013-05-22)
Type-2 diabetes is one of the fastest growing public health problems worldwide resulting from both environmental and genetic factors. Activation of μ-opioid receptor (MOR) could result in reversal of the impairment of insulin-stimulated glucose disposal in genetically obese Zucker rats

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