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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H33ClN2O3
Molecular Weight 493.0379
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOPERAMIDE OXIDE ANHYDROUS

SMILES

CN(C)C(=O)C(CC[N@]1(=O)CC[C@](CC1)(c2ccc(cc2)Cl)O)(c3ccccc3)c4ccccc4

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 493.0379
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Dose proportionality study of loperamide following oral administration of loperamide oxide.
1992
Effects of the prodrug loperamide oxide, loperamide, and placebo on jejunal motor activity.
1992 Feb
Influence of loperamide and loperamide oxide on the anal sphincter. A manometric study.
1992 Sep
Loperamide oxide in the treatment of acute diarrhea in adults.
1994 Nov-Dec

Sample Use Guides

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 Sat Jun 26 09:14:06 UTC 2021
Edited
by admin
on Sat Jun 26 09:14:06 UTC 2021
Record UNII
NG66S4H2RL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
LOPERAMIDE RELATED COMPOUND F
USP-RS  
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
LOPERAMIDE OXIDE [WHO-DD]
Common Name English
R-58425
Code English
LOPERAMIDE HYDROCHLORIDE IMPURITY F [EP]
Common Name English
Classification Tree Code System Code
WHO-ATC A07DA05
Created by admin on Sat Jun 26 09:14:07 UTC 2021 , Edited by admin on Sat Jun 26 09:14:07 UTC 2021
Code System Code Type Description
FDA UNII
NG66S4H2RL
Created by admin on Sat Jun 26 09:14:07 UTC 2021 , Edited by admin on Sat Jun 26 09:14:07 UTC 2021
PRIMARY
EVMPD
SUB27172
Created by admin on Sat Jun 26 09:14:07 UTC 2021 , Edited by admin on Sat Jun 26 09:14:07 UTC 2021
PRIMARY
INN
6139
Created by admin on Sat Jun 26 09:14:07 UTC 2021 , Edited by admin on Sat Jun 26 09:14:07 UTC 2021
PRIMARY
EVMPD
SUB08573MIG
Created by admin on Sat Jun 26 09:14:07 UTC 2021 , Edited by admin on Sat Jun 26 09:14:07 UTC 2021
PRIMARY
NCI_THESAURUS
C174757
Created by admin on Sat Jun 26 09:14:07 UTC 2021 , Edited by admin on Sat Jun 26 09:14:07 UTC 2021
PRIMARY
CAS
106900-12-3
Created by admin on Sat Jun 26 09:14:07 UTC 2021 , Edited by admin on Sat Jun 26 09:14:07 UTC 2021
PRIMARY
USP_CATALOG
1370065
Created by admin on Sat Jun 26 09:14:07 UTC 2021 , Edited by admin on Sat Jun 26 09:14:07 UTC 2021
PRIMARY USP-RS
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP