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Loperamide

Loperamide Structure
CAS No.
53179-11-6
Chemical Name:
Loperamide
Synonyms
C07080;Tebloc;utanamide;LOPERAMIDE;Loperamide Monomer;Loperamide USP/EP/BP;4-(4-chlorophenyl)-n,n-dimethyl-alpha;4-(4-chlorophenyl)-n,n-dimethyl-alpha,alpha-diphenyl-4-hydroxy-1-piperidineb;4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-,-diphenyl-1-p-piperidinebutanamide;4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutyramide
CBNumber:
CB7402928
Molecular Formula:
C29H33ClN2O2
Molecular Weight:
477.04
MOL File:
53179-11-6.mol
MSDS File:
SDS
Modify Date:
2024/3/19 15:37:50

Loperamide Properties

Boiling point 647.2±55.0 °C(Predicted)
Density 1.187±0.06 g/cm3(Predicted)
pka pKa 8.66(H2O) (Uncertain)
BCS Class 4
LogP 2.641 at 25℃ and pH6.95
CAS DataBase Reference 53179-11-6(CAS DataBase Reference)
NIST Chemistry Reference Loperamide(53179-11-6)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P321-P330-P405-P501

Loperamide Chemical Properties,Uses,Production

Uses

Loperamide is presently used more often as an antidiarrheal drug than as an analgesic, and it is also included in the list of over-the-counter drugs because of its insignificant action on the CNS. It reduces intestinal smooth muscle tone and motility as a result of binding to intestinal opiate receptors. It is used for symptomatic treatment of severe and chronic diarrhea of various origins. The most popular synonym for loperamide is imodium.

Definition

ChEBI: A synthetic piperidine derivative, effective against diarrhoea resulting from gastroenteritis or inflammatory bowel disease.

World Health Organization (WHO)

Loperamide, an inhibitor of intestinal peristalsis, was introduced in 1975 for the treatment of acute and chronic diarrhoea. In many countries its use was discouraged in young children. In late 1989, treatment of infants in Pakistan was associated with 19 cases of paralytic ileus, 6 of which have been fatal. This has subsequently led the major manufacturer to withdraw all drop formulations of the drug worldwide as well as the lower dose syrup forms from countries where there is a programme for the control of diarrhoeal diseases. The WHO Control of Diarrhoeal Diseases Programme recommends that loperamide should not be used in children below five year of age. (Reference: (LJJ) Letter to WHO from Johnson & Johnson, , , 21 June 1990)

General Description

Loperamide (Imodium) is a 4-phenylypiperidine with amethadone-like structure attached to the piperidine nitrogen. It acts as an antidiarrheal by directly binding tothe opiate receptors in the gut wall. Loperamide inhibitsacetylcholine and prostaglandin release, decreasing peristalsisand fluid secretion thus increasing the GI transit time andreducing the volume of fecal matter.Loperamide is sufficiently lipophilic to cross the blood-brain barrier, yet itdisplays no CNS-opioid effects. The reason for this is that itis actively pumped out of the brain via the P-glycoproteinpump (MDR1). Knockout mice with the P-glycoproteinpump genetically removed were given radiolabeled loperamideand sacrificed 4 hours later. The [3H]loperamideconcentrations were measured and compared with wild-typemice. A 13.5-fold increase in loperamide concentration wasfound in the brain of the knockouts. In addition, the micelacking the P-glycoprotein pump displayed pronouncedsigns of central opiate agonism. Loperamide is availableas 2-mg capsules for treatment of acute and chronic diarrhea.Recommended dosage is 4 mg initially, with 2 mgafter each loose stool for a maximum of 16 mg/d.

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4-[4-Chlorophenyl]-4-hydroxy-N, N-dimethyl-α,α-diphenyl-1-piperidinebutanamide 4-[4-(4-chlorophenyl)-4-hydroxy-1-piperidyl]-N,N-dimethyl-2,2-diphenyl-butanamide 4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-,-diphenyl-1-p-piperidinebutanamide LOPERAMIDE 4-[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-di(phenyl)butanamide 4-(4-CHLOROPHENYL)-4-HYDROXY-N,N DIMETHYL-A,A DIPHENYL-1-PEIPERIDINE BUTANAMIDEHCL 4-(4-chlorophenyl)-n,n-dimethyl-alpha,alpha-diphenyl-4-hydroxy-1-piperidineb 4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutyramide 4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-2,2-diphenyl-N,N-dimethylbutyramide 4-[4-Hydroxy-4-(4-chlorophenyl)-1-piperidinyl]-2,2-diphenyl-N,N-dimethylbutanamide C07080 Tebloc utanamide 4-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]-N,N-dimethyl-2,2-diphenylbutanamide 4-(4-chlorophenyl)-n,n-dimethyl-alpha 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-α,α-diphenyl- Loperamide USP/EP/BP LoperamideQ: What is Loperamide Q: What is the CAS Number of Loperamide Q: What is the storage condition of Loperamide 4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-a,a-diphenyl-1-piperidinebutanamide Loperamide 4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-N,N-dimethyl- 2,2-diphenylbutanamide Loperamide Monomer 53179-11-6 C29H33ClN2O2