U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C29H33ClN2O3.H2O
Molecular Weight 511.052
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOPERAMIDE OXIDE MONOHYDRATE

SMILES

O.CN(C)C(=O)C(CC[N@+]1([O-])CC[C@](O)(CC1)C2=CC=C(Cl)C=C2)(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=MVMJRVIHTNVDRP-AYFKLSOTSA-N
InChI=1S/C29H33ClN2O3.H2O/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;1H2/t28-,32-;

HIDE SMILES / InChI

Description

Loperamide Oxide is a prodrug of loperamide, an antidiarrheal agent, patented by Belgian pharmaceutical company Janssen Pharmaceutica N. V. as an antidiarrheal agent. Loperamide oxide is reduced to loperamide and has the same antisecretory potency as loperamide in jejunum and colon. In clinical trials, Loperamide oxide provides a safe and effective treatment for chronic diarrhea associated with Crohn's disease. Loperamide Oxide is used in the Netherlands for the treatment of acute diarrhea in adults under brand name Arestal.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

PubMed

Sample Use Guides

In Vivo Use Guide
1 or 2 mg after passage of each unformed stool for 1-week The mean daily dose of loperamide oxide was 2.7 mg.
Route of Administration: Oral