LOPERAMIDE OXIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H33ClN2O3
Molecular Weight	493.037
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=KXVSBTJVTUVNPM-UKPNQBOSSA-N

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/t28-,32-

HIDE SMILES / InChI

Molecular Formula	C29H33ClN2O3
Molecular Weight	493.037
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/international/loperamide-oxide.html | https://www.ncbi.nlm.nih.gov/pubmed/1735336 | https://www.ncbi.nlm.nih.gov/pubmed/7697694

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 Target	Pharmacology	Condition	Potency
oxidation-reduction process 2 Target ID: GO:0055114 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7628301	Substrate 661

PubMed

Title	Date	PubMed
Loperamide oxide in the treatment of acute diarrhea in adults.	1994-11-01	7697694
Influence of loperamide and loperamide oxide on the anal sphincter. A manometric study.	1992-09	1511646
Effects of the prodrug loperamide oxide, loperamide, and placebo on jejunal motor activity.	1992-02	1735336
Dose proportionality study of loperamide following oral administration of loperamide oxide.	1992	1623916

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:22:38 GMT 2025` Edited by `admin` on `Mon Mar 31 19:22:38 GMT 2025`
Record UNII	NG66S4H2RL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOPERAMIDE OXIDE

Official Name

English

LOPERAMIDE RELATED COMPOUND F

Preferred Name

English

Loperamide oxide [WHO-DD]

Common Name

English

LOPERAMIDE HYDROCHLORIDE IMPURITY F [EP IMPURITY]

Common Name

English

LOPERAMIDE OXIDE ANHYDROUS

Common Name

English

TRANS-4-(P-CHLOROPHENYL)-4-HYDROXY-N,N-DIMETHYL-.ALPHA.,.ALPHA.-DIPHENYL-1-PIPERIDINEBUTYRAMIDE 1-OXIDE

Common Name

English

4-(TRANS-4-(4-CHLOROPHENYL)-4-HYDROXY-1-OXIDOPIPERIDIN-1-YL)-N,N-DIMETHYL-2,2-DIPHENYLBUTANAMIDE

Systematic Name

English

loperamide oxide [INN]

Common Name

English

LOPERAMIDE RELATED COMPOUND F [USP-RS]

Common Name

English

1-PIPERIDINEBUTANAMIDE, 4-(4-CHLOROPHENYL)-4-HYDROXY-N,N-DIMETHYL-.ALPHA.,.ALPHA.-DIPHENYL-, 1-OXIDE, TRANS-

Systematic Name

English

R-58425

Code

English

Classification Tree Code System Code

WHO-ATC

A07DA05