Compounds > loperamide oxide
Page last updated: 2024-11-06

loperamide oxide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

loperamide oxide: RN given refers to (trans)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID71421
CHEMBL ID2105114
CHEBI ID135795
SCHEMBL ID692910
SCHEMBL ID1651792
SCHEMBL ID10376326
MeSH IDM0181370

Synonyms (64)

Synonym
106900-12-3
loperamide oxide (inn)
D07113
r 58425
loperamide oxide [inn:ban]
loperamide oxide
loperamide n-oxide
trans-4-(p-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-1-piperidinebutyramide 1-oxide
1-piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-, 1-oxide, (e)-
trans-n-oxide of loperamide
loperamidum oxidum [latin]
oxido de loperamida [spanish]
loperamide oxyde [french]
CHEBI:135795
4-[4-(4-chlorophenyl)-4-hydroxy-1-oxidopiperidin-1-ium-1-yl]-n,n-dimethyl-2,2-diphenylbutanamide
loperamide oxyde
r58425
oxido de loperamida
ng66s4h2rl ,
unii-ng66s4h2rl
loperamidum oxidum
CHEMBL2105114
r-58425
loperamide oxide anhydrous
loperamide oxide monohydrate
arestal
FT-0670838
1-piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-, 1-oxide, cis-
4-(cis-4-(4-chlorophenyl)-4-hydroxy-1-oxidopiperidin-1-yl)-n,n-dimethyl-2,2-diphenylbutanamide
109572-89-6
loperamide oxide anhydrous, cis-
unii-ywt7aj7o7p
loperamide hydrochloride specified impurity g [ep]
ywt7aj7o7p ,
loperamide hydrochloride impurity f [ep impurity]
4-(trans-4-(4-chlorophenyl)-4-hydroxy-1-oxidopiperidin-1-yl)-n,n-dimethyl-2,2-diphenylbutanamide
loperamide oxide [who-dd]
loperamide oxide [inn]
1-piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-.alpha.,.alpha.-diphenyl-, 1-oxide, trans-
trans-4-(p-chlorophenyl)-4-hydroxy-n,n-dimethyl-.alpha.,.alpha.-diphenyl-1-piperidinebutyramide 1-oxide
SCHEMBL692910
loperamide oxide, cis-
1-piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-.alpha.,.alpha.-diphenyl-, 1-oxide, cis-
loperamide oxide monohydrate impurity b [ep impurity]
loperamide hydrochloride impurity g [ep impurity]
SCHEMBL1651792
SCHEMBL10376326
loperamide ep impurity g
J-001673
4-[cis-4-(4-chlorophenyl)-4-hydroxy-1-oxidopiperidin-1-yl]-n,n-dimethyl-2,2-diphenylbutanamide (loperamide cis-n-oxide)
4-[cis-4-(4-chlorophenyl)-4-hydroxy-1-oxidopiperidin-1-yl]-n,n-dimethyl-2,2-diphenylbutanamide; cis-loperamide n-oxide; loperamide hydrochloride imp. g (ep); 1-piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-, 1-oxide,
DTXSID80883171
DB14661
217471-03-9
4-(4-chlorophenyl)-1-(4-(dimethylamino)-4-oxo-3,3-diphenylbutyl)-4-hydroxypiperidine 1-oxide
(1r,4s)-4-(4-chlorophenyl)-1-(4-(dimethylamino)-4-oxo-3,3-diphenylbutyl)-4-hydroxypiperidine 1-oxide
Q27284849
Q27294750
cis-loperamide oxide
4-[cis-4-(4-chlorophenyl)-4-hydroxy-1-oxidopiperidin-1-yl]-n,n-dimethyl-2,2-diphenylbutanamide
A937242
DTXSID10869468
4-[4-(4-chlorophenyl)-4-hydroxy-1-oxo-1lambda~5~-piperidin-1-yl]-n,n-dimethyl-2,2-diphenylbutanamide
AKOS040747115

Research Excerpts

Overview

Loperamide oxide is a prodrug of the effective antidiarrheal loperamide.

ExcerptReferenceRelevance
"Loperamide oxide (LOPOX) is a prodrug of loperamide (LOP). "( Reduction of the prodrug loperamide oxide to its active drug loperamide in the gut of rats, dogs, and humans.
Hendrickx, J; Heykants, J; Lavrijsen, K; Meuldermans, W; Monbaliu, J; van Dyck, D; van Houdt, J; Woestenborghs, R, 1995)		2.04
"Loperamide oxide is a prodrug of the effective antidiarrheal loperamide. "( Gastrointestinal distribution of the prodrug loperamide oxide and its active drug loperamide in the dog.
Geerts, RJ; Heykants, JJ; Meuldermans, WE; Van Beijsterveldt, LE; Woestenborghs, RJ; Wuyts, K, 1995)		1.99

Toxicity

ExcerptReferenceRelevance
"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."( Identification of an N-methyl-4-phenylpyridinium-like metabolite of the antidiarrheal agent loperamide in human liver microsomes: underlying reason(s) for the lack of neurotoxicity despite the bioactivation event.
Kalgutkar, AS; Nguyen, HT, 2004)		0.32

Bioavailability

ExcerptReferenceRelevance
" Comparison of the maximum plasma loperamide concentration and AUC demonstrated that the bioavailability of loperamide was proportional to the dose of loperamide oxide administered."( Dose proportionality study of loperamide following oral administration of loperamide oxide.
Adriaens, L; Emanuel, M; Huang, ML; Kamali, F; Rawlins, MD; Woestenborghs, R, 1992)		0.71

Dosage Studied

ExcerptRelevanceReference
" A dose-response relationship was demonstrated at 2 h in the jejunum and the colon."( Antisecretory activities of orally administered loperamide and loperamide oxide on intestinal secretion in rats.
Badhri, P; Beubler, E; Schirgi-Degen, A, 1993)		0.53
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's14 (87.50)18.2507
2000's2 (12.50)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.37

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index27.37 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.15 (4.65)
Search Engine Demand Index22.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials10 (52.63%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (47.37%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
bupropion
Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.. bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.		2.0210aromatic ketone;
monochlorobenzenes;
secondary amino compound		antidepressant;
environmental contaminant;
xenobiotic
glycine
[no description available]		1.9810alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine: A dopaminergic neurotoxic compound which produces irreversible clinical, chemical, and pathological alterations that mimic those found in Parkinson disease.. 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine : A tetrahydropyridine that is 1,2,3,6-tetrahydropyridine substituted by a methyl group at position 1 and a phenyl group at position 4.		2.0210methylpyridines;
phenylpyridine;
tetrahydropyridine		neurotoxin
haloperidol
Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.		2.0210aromatic ketone;
hydroxypiperidine;
monochlorobenzenes;
organofluorine compound;
tertiary alcohol		antidyskinesia agent;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic;
serotonergic antagonist
ketoconazole
1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively.		2.0210dichlorobenzene;
dioxolane;
ether;
imidazoles;
N-acylpiperazine;
N-arylpiperazine
loperamide
Loperamide: One of the long-acting synthetic ANTIDIARRHEALS; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally.. loperamide : A synthetic piperidine derivative, effective against diarrhoea resulting from gastroenteritis or inflammatory bowel disease.		8.13167monocarboxylic acid amide;
monochlorobenzenes;
piperidines;
tertiary alcohol		anticoronaviral agent;
antidiarrhoeal drug;
mu-opioid receptor agonist
1-methyl-4-phenylpyridinium
1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.		2.0210pyridinium ionapoptosis inducer;
herbicide;
human xenobiotic metabolite;
neurotoxin
n-(4'-fluorobutyrophenone)-4-(4-chlorophenyl)pyridinium
N-(4'-fluorobutyrophenone)-4-(4-chlorophenyl)pyridinium: a neurotoxic quaternary haloperidol metabolite in rat liver; structure in first source		2.0210
trimethoprim, sulfamethoxazole drug combination
Trimethoprim, Sulfamethoxazole Drug Combination: A drug combination with broad-spectrum antibacterial activity against both gram-positive and gram-negative organisms. It is effective in the treatment of many infections, including PNEUMOCYSTIS PNEUMONIA in AIDS.. co-trimoxazole : A two-component mixture comprising trimethoprim and sulfamethoxazole.		3.3711
nadp
[no description available]		2.0210
dinoprostone
prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.		2.3820prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic
naloxone
Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.		1.9710morphinane alkaloid;
organic heteropentacyclic compound;
tertiary alcohol		antidote to opioid poisoning;
central nervous system depressant;
mu-opioid receptor antagonist
n-demethylloperamide
N-demethylloperamide: loperamide metabolite; structure in first source. desmethyl loperamide : A monocarboxylic acid amide that is the methylamide of 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenylbutanoic acid.		2.0210monocarboxylic acid amide;
monochlorobenzenes;
piperidines;
tertiary alcohol		drug metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Chronic Illness
[description not available]		05.2522
Injuries, Radiation
[description not available]		03.3711
Genito-urinary Cancer
[description not available]		03.3711
Chronic Disease
Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).		05.2522
Diarrhea
An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.		05.933
Enteritis
Inflammation of any segment of the SMALL INTESTINE.		03.3711
Urogenital Neoplasms
Tumors or cancer of the UROGENITAL SYSTEM in either the male or the female.		03.3711
Bowel Incontinence
[description not available]		04.2911
Fecal Incontinence
Failure of voluntary control of the anal sphincters, with involuntary passage of feces and flatus.		04.2911
Colonic Diseases, Functional
Chronic or recurrent colonic disorders without an identifiable structural or biochemical explanation. The widely recognized IRRITABLE BOWEL SYNDROME falls into this category.		0210