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Y0000341

Loperamide oxide monohydrate

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

trans-4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutanamide 1-oxide monohydrate

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About This Item

Empirical Formula (Hill Notation):
C29H33ClN2O3 · H2O
CAS Number:
Molecular Weight:
511.05
UNSPSC Code:
41116107
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

loperamide

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

Clc1ccc(cc1)C2(CC[N](=O)(CC2)CCC(c4ccccc4)(c3ccccc3)C(=O)N(C)C)O

InChI

1S/C29H33ClN2O3/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32(35)20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3

InChI key

KXVSBTJVTUVNPM-UHFFFAOYSA-N

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Loperamide oxide monohydrate EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

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 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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J Hardcastle et al.
The Journal of pharmacy and pharmacology, 42(5), 364-366 (1990-05-01)
The effects of loperamide and loperamide oxide on basal and prostaglandin E2-stimulated fluid transport by rat small intestine have been investigated. In contrast to loperamide, loperamide oxide, when applied intraperitoneally, failed to inhibit either basal or prostaglandin E2-stimulated fluid transport.
A Dettmer
Clinical therapeutics, 16(6), 972-980 (1994-11-01)
We evaluated two doses of loperamide oxide (1 mg and 2 mg) and placebo in the treatment of acute diarrhea in 230 adult patients. Two tablets were taken initially and then one tablet after each watery, loose, or pasty stool
Amit S Kalgutkar et al.
Drug metabolism and disposition: the biological fate of chemicals, 32(9), 943-952 (2004-08-21)
In contrast with the Parkinson's-like effects associated with the mitochondrial neurotoxin N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and the neuroleptic agent haloperidol, there exist no reports on adverse central nervous system (CNS) effects with the structurally related N-substituted-4-arylpiperidin-4-ol derivative and antidiarrheal agent loperamide. Although
J W Dreverman et al.
Alimentary pharmacology & therapeutics, 9(4), 441-446 (1995-08-01)
Loperamide is an established treatment of acute diarrhoea with only rare adverse reactions. The pro-drug loperamide oxide is converted to loperamide by anaerobic bacteria in the lower alimentary tract. With the use of loperamide oxide, it was expected to obtain
E Beubler et al.
The Journal of pharmacy and pharmacology, 45(9), 803-806 (1993-09-01)
In-vivo experiments in the rat jejunum have been performed to compare the antisecretory effect of orally administered loperamide with the effect of its pro-drug, loperamide oxide. Both loperamide and loperamide oxide, administered orally, reduced the secretory effect of prostaglandin E2

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