Identification

Name
Loperamide
Accession Number
DB00836  (APRD00275)
Type
Small Molecule
Groups
Approved
Description

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. [PubChem]

Structure
Thumb
Synonyms
  • Loperamid
  • Loperamida
  • Lopéramide
  • Loperamidum
External IDs
PJ 185 / R 18553
Product Ingredients
IngredientUNIICASInChI Key
Loperamide hydrochloride77TI35393C34552-83-5PGYPOBZJRVSMDS-UHFFFAOYSA-N
Loperamide oxideNG66S4H2RL106900-12-3KXVSBTJVTUVNPM-UHFFFAOYSA-N
Product Images
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Loperamide HydrochlorideCapsule2 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2012-10-12Not applicableUs
Loperamide HydrochlorideCapsule2 mg/1OralAidarex Pharmaceuticals LLC1993-05-01Not applicableUs
Loperamide HydrochlorideCapsule2 mg/1OralContract Pharmacy Services Pa2017-09-20Not applicableUs
Loperamide HydrochlorideCapsule2 mg/1OralCardinal Health1991-09-182015-12-29Us
Loperamide HydrochlorideCapsule2 mg/1OralDirectrx2014-01-01Not applicableUs
Loperamide HydrochlorideCapsule2 mg/1OralRemedy Repack2016-12-12Not applicableUs
Loperamide HydrochlorideCapsule2 mg/1OralMylan Institutional1997-03-10Not applicableUs
Loperamide HydrochlorideCapsule2 mg/1OralNucare Pharmaceuticals, Inc.1993-05-01Not applicableUs
Loperamide HydrochlorideCapsule2 mg/1OralNu Care Pharmceuticals,inc.1993-05-01Not applicableUs
Loperamide HydrochlorideCapsule2 mg/1OralRemedy Repack2017-12-12Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
7 Select Anti DiarrhealTablet, film coated2 mg/1Oral7 Eleven2014-08-05Not applicableUs
A DTablet, film coated2 mg/1OralWestern Family Foods2003-02-252017-12-01Us
A DTablet, film coated2 mg/1OralWestern Family Foods2003-04-102017-12-01Us
Alti-loperamide - 2mg CapletTablet2 mgOralAltimed Pharma Inc.1995-12-311997-08-14Canada
Anti DiarrhealTablet, film coated2 mg/1OralRemedy Repack2017-10-11Not applicableUs
Anti DiarrhealCapsule2 mg/1OralNash Finch2005-05-032018-04-02Us
Anti DiarrhealTablet2 mg/1OralArmy + Air Force Exchange Service2005-05-03Not applicableUs
Anti DiarrhealTablet, film coated2 mg/1OralPreferreed Pharmaceuticals Inc.2015-11-20Not applicableUs
Anti DiarrhealTablet, film coated2 mg/1OralCVS Health2003-02-24Not applicableUs
Anti DiarrhealTablet, film coated2 mg/1OralRemedy Repack2016-05-172018-06-07Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Doc in the Box All Day SupplyLoperamide hydrochloride + Acetaminophen + Calcium Carbonate + Dextromethorphan hydrobromide + Guaifenesin + Ibuprofen + Phenylephrine hydrochlorideKitOralDoc In The Box Llc2018-05-14Not applicableUs
Imodium Complete CapletsLoperamide hydrochloride (2 mg) + Simethicone (125 mg)TabletOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc2002-06-20Not applicableCanada
Imodium Complete Chewable TabletsLoperamide hydrochloride (2 mg) + Simethicone (125 mg)Tablet, chewableOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1998-05-12Not applicableCanada
IMODIUM Multi-Symptom ReliefLoperamide hydrochloride (2 mg/1) + Dimethicone (125 mg/1)TabletOralJohnson & Johnson Consumer Inc., Mc Neil Consumer Healthcare Division2008-07-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Gadavyt Loperamide HClLoperamide hydrochloride (1 mg/5mL)LiquidOralGadal Laboratories, Inc.2013-05-01Not applicableUs
International/Other Brands
Dimor (Nordic Drugs) / Fortasec (Esteve) / Imodium (Johnson & Johnson) / Kaopectate II (Chattem, Inc.) / Lopedium (Sandoz) / Lopedium express (Sandoz) / Lopex (Orion) / Maalox Anti-Diarrheal (Novartis International AG) / Pepto Diarrhea Control (Procter & Gamble )
Categories
UNII
6X9OC3H4II
CAS number
53179-11-6
Weight
Average: 477.038
Monoisotopic: 476.223056017
Chemical Formula
C29H33ClN2O2
InChI Key
RDOIQAHITMMDAJ-UHFFFAOYSA-N
InChI
InChI=1S/C29H33ClN2O2/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3
IUPAC Name
4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
SMILES
CN(C)C(=O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

For the control and symptomatic relief of acute nonspecific diarrhea and of chronic diarrhea associated with inflammatory bowel disease or gastroenteritis. Also used for reducing the volume of discharge from ileostomies.

Associated Conditions
Pharmacodynamics

Loperamide is a synthetic anti-diarrheal indicated for the control and symptomatic relief of acute nonspecific diarrhea and of chronic diarrhea associated with inflammatory bowel disease. Loperamide is also indicated for reducing the volume of discharge from ileostomies. In man, Loperamide prolongs the transit time of the intestinal contents. It reduces the daily fecal volume, increases the viscosity and bulk density, and diminishes the loss of fluid and electrolytes. Tolerance to the antidiarrheal effect has not been observed. Loperamide is an opioid receptor agonist and acts on the mu opioid receptors in the myenteric plexus large intestines; it does not affect the central nervous system like other opioids. It works specifically by decreasing the activity of the myenteric plexus which decreases the motility of the circular and longitudinal smooth muscles of the intestinal wall. This increases the amount of time substances stay in the intestine, allowing for more water to be absorbed out of the fecal matter. Loperamide also decreases colonic mass movements and suppresses the gastrocolic reflex.

Mechanism of action

In vitro and animal studies show that Loperamide acts by slowing intestinal motility and by affecting water and electrolyte movement through the bowel. Loperamide inhibits peristaltic activity by a direct effect on the circular and longitudinal muscles of the intestinal wall. It is a non-selective calcium channel blocker and binds to opioid mu-receptors. Evidence also suggests that at higher concentrations it binds to calmodulin.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Human
ADelta-type opioid receptor
agonist
Human
AKappa-type opioid receptor
agonist
Human
UVoltage-dependent P/Q-type calcium channel subunit alpha-1A
inhibitor
Human
UPro-opiomelanocortin
modulator
Human
UCalmodulin
inhibitor
Human
UNuclear receptor subfamily 1 group I member 3Not AvailableHuman
Absorption

Not significantly absorbed from the gut

Volume of distribution
Not Available
Protein binding

97%

Metabolism

Hepatic

Route of elimination

Excretion of the unchanged loperamide and its metabolites mainly occurs through the feces.

Half life

9.1 to 14.4 hours (average 10.8 hours)

Clearance
Not Available
Toxicity

Oral, mouse: LD50 = 105 mg/kg. Symptoms of overdose include constipation, drowsiness, lethargy, and nausea.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2-HYDROXY-1,4-NAPHTHOQUINONEThe therapeutic efficacy of 2-HYDROXY-1,4-NAPHTHOQUINONE can be increased when used in combination with Loperamide.Experimental
2-mercaptobenzothiazoleThe therapeutic efficacy of 2-mercaptobenzothiazole can be increased when used in combination with Loperamide.Vet Approved
AbirateroneThe serum concentration of Loperamide can be increased when it is combined with Abiraterone.Approved
AcepromazineThe risk or severity of hypotension can be increased when Acepromazine is combined with Loperamide.Approved, Vet Approved
Acetyl sulfisoxazoleThe metabolism of Loperamide can be decreased when combined with Acetyl sulfisoxazole.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Loperamide.Approved
AlfuzosinThe risk or severity of hypotension can be increased when Alfuzosin is combined with Loperamide.Approved, Investigational
AmiodaroneThe metabolism of Loperamide can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe risk or severity of hypotension can be increased when Amitriptyline is combined with Loperamide.Approved
AmobarbitalThe metabolism of Loperamide can be increased when combined with Amobarbital.Approved, Illicit
AmorolfineThe therapeutic efficacy of Amorolfine can be increased when used in combination with Loperamide.Approved, Investigational
AmoxapineThe risk or severity of hypotension can be increased when Amoxapine is combined with Loperamide.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be increased when used in combination with Loperamide.Approved, Investigational
AnidulafunginThe therapeutic efficacy of Anidulafungin can be increased when used in combination with Loperamide.Approved, Investigational
ApalutamideThe serum concentration of Loperamide can be decreased when it is combined with Apalutamide.Approved, Investigational
AprepitantThe serum concentration of Loperamide can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe risk or severity of hypotension can be increased when Aripiprazole is combined with Loperamide.Approved, Investigational
ArotinololThe risk or severity of hypotension, conduction block, and bradycardia can be increased when Arotinolol is combined with Loperamide.Investigational
ArtemetherThe metabolism of Loperamide can be decreased when combined with Artemether.Approved
AsenapineThe risk or severity of hypotension can be increased when Asenapine is combined with Loperamide.Approved
AtazanavirThe metabolism of Loperamide can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Loperamide can be decreased when combined with Atomoxetine.Approved
Bafilomycin A1The therapeutic efficacy of Bafilomycin A1 can be increased when used in combination with Loperamide.Experimental
BarbexacloneThe metabolism of Loperamide can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Loperamide can be increased when combined with Barbital.Illicit
Benzoic AcidThe therapeutic efficacy of Benzoic Acid can be increased when used in combination with Loperamide.Approved, Investigational
BetaxololThe metabolism of Loperamide can be decreased when combined with Betaxolol.Approved, Investigational
BevantololThe risk or severity of hypotension can be increased when Bevantolol is combined with Loperamide.Approved
BifonazoleThe therapeutic efficacy of Bifonazole can be increased when used in combination with Loperamide.Approved, Investigational
BoceprevirThe metabolism of Loperamide can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Loperamide can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Loperamide can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Loperamide.Approved
Brefeldin AThe therapeutic efficacy of Brefeldin A can be increased when used in combination with Loperamide.Experimental
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Loperamide.Approved, Investigational
BrexpiprazoleThe risk or severity of hypotension can be increased when Brexpiprazole is combined with Loperamide.Approved, Investigational
BucindololThe risk or severity of hypotension can be increased when Bucindolol is combined with Loperamide.Investigational
BunazosinThe risk or severity of hypotension can be increased when Bunazosin is combined with Loperamide.Investigational
BupropionThe metabolism of Loperamide can be decreased when combined with Bupropion.Approved
ButenafineThe therapeutic efficacy of Butenafine can be increased when used in combination with Loperamide.Approved
ButoconazoleThe therapeutic efficacy of Butoconazole can be increased when used in combination with Loperamide.Approved
Calcium AcetateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium Acetate.Approved, Investigational
Calcium CarbonateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium Carbonate.Approved, Investigational
Calcium ChlorideThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium Chloride.Approved
Calcium CitrateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium Citrate.Approved
Calcium glubionateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium glubionate.Approved
Calcium GluceptateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium Gluceptate.Approved
Calcium gluconateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium gluconate.Approved, Vet Approved
Calcium lactateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium lactate.Approved, Investigational, Vet Approved
Calcium lactate gluconateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium lactate gluconate.Experimental
Calcium levulinateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium levulinate.Approved, Experimental
Calcium pangamateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium pangamate.Experimental
Calcium PhosphateThe therapeutic efficacy of Loperamide can be decreased when used in combination with Calcium Phosphate.Approved
CandicidinThe therapeutic efficacy of Candicidin can be increased when used in combination with Loperamide.Withdrawn
Capric acidThe therapeutic efficacy of Capric acid can be increased when used in combination with Loperamide.Experimental
CarbamazepineThe metabolism of Loperamide can be increased when combined with Carbamazepine.Approved, Investigational
CarvedilolThe risk or severity of hypotension can be increased when Carvedilol is combined with Loperamide.Approved, Investigational
CaseinThe therapeutic efficacy of Loperamide can be decreased when used in combination with Casein.Approved
CaspofunginThe therapeutic efficacy of Caspofungin can be increased when used in combination with Loperamide.Approved
CelecoxibThe metabolism of Loperamide can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Loperamide can be increased when it is combined with Ceritinib.Approved
CeruleninThe therapeutic efficacy of Cerulenin can be increased when used in combination with Loperamide.Approved
ChloroquineThe metabolism of Loperamide can be decreased when combined with Chloroquine.Approved, Investigational, Vet Approved
ChloroxineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Loperamide.Approved
ChlorpromazineThe metabolism of Loperamide can be decreased when combined with Chlorpromazine.Approved, Investigational, Vet Approved
CholecalciferolThe metabolism of Loperamide can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CiclopiroxThe therapeutic efficacy of Ciclopirox can be increased when used in combination with Loperamide.Approved, Investigational
CimetidineThe serum concentration of Loperamide can be increased when it is combined with Cimetidine.Approved, Investigational
CinacalcetThe metabolism of Loperamide can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Loperamide can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Loperamide can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Loperamide can be decreased when combined with Clemastine.Approved, Investigational
ClobazamThe metabolism of Loperamide can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Loperamide can be decreased when combined with Clomipramine.Approved, Investigational, Vet Approved
ClopidogrelThe therapeutic efficacy of Clopidogrel can be decreased when used in combination with Loperamide.Approved
ClotrimazoleThe metabolism of Loperamide can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Loperamide can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Loperamide can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Loperamide can be decreased when combined with Cocaine.Approved, Illicit
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Loperamide.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Loperamide.Approved, Investigational
CordycepinThe therapeutic efficacy of Cordycepin can be increased when used in combination with Loperamide.Investigational
CrisaboroleThe metabolism of Loperamide can be decreased when combined with Crisaborole.Approved, Investigational
CrizotinibThe metabolism of Loperamide can be decreased when combined with Crizotinib.Approved
CurcuminThe metabolism of Loperamide can be decreased when combined with Curcumin.Approved, Investigational
CyclosporineThe metabolism of Loperamide can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Loperamide.Approved
DabrafenibThe serum concentration of Loperamide can be decreased when it is combined with Dabrafenib.Approved, Investigational
DapiprazoleThe risk or severity of hypotension can be increased when Dapiprazole is combined with Loperamide.Approved
DarifenacinThe metabolism of Loperamide can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Loperamide can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Loperamide can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Loperamide can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Loperamide can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Loperamide can be decreased when combined with Desipramine.Approved, Investigational
DextroamphetamineThe risk or severity of hypotension can be increased when Dextroamphetamine is combined with Loperamide.Approved, Illicit
DichloropheneThe therapeutic efficacy of Dichlorophene can be increased when used in combination with Loperamide.Vet Approved
DihydroergotamineThe metabolism of Loperamide can be decreased when combined with Dihydroergotamine.Approved, Investigational
DiltiazemThe metabolism of Loperamide can be decreased when combined with Diltiazem.Approved, Investigational
DiphenhydramineThe metabolism of Loperamide can be decreased when combined with Diphenhydramine.Approved, Investigational
DosulepinThe metabolism of Loperamide can be decreased when combined with Dosulepin.Approved
DoxazosinThe risk or severity of hypotension can be increased when Doxazosin is combined with Loperamide.Approved
DoxepinThe risk or severity of hypotension can be increased when Doxepin is combined with Loperamide.Approved, Investigational
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Loperamide.Approved, Investigational
DoxorubicinThe metabolism of Loperamide can be decreased when combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Loperamide can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Loperamide can be decreased when combined with Dronedarone.Approved
DroperidolThe risk or severity of hypotension can be increased when Droperidol is combined with Loperamide.Approved, Vet Approved
DuloxetineThe metabolism of Loperamide can be decreased when combined with Duloxetine.Approved
EconazoleThe therapeutic efficacy of Econazole can be increased when used in combination with Loperamide.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Loperamide.Approved
EfavirenzThe serum concentration of Loperamide can be decreased when it is combined with Efavirenz.Approved, Investigational
EfinaconazoleThe therapeutic efficacy of Efinaconazole can be increased when used in combination with Loperamide.Approved
EliglustatThe metabolism of Loperamide can be decreased when combined with Eliglustat.Approved
EnzalutamideThe serum concentration of Loperamide can be decreased when it is combined with Enzalutamide.Approved
EpinephrineThe risk or severity of hypotension can be increased when Epinephrine is combined with Loperamide.Approved, Vet Approved
ErythromycinThe metabolism of Loperamide can be decreased when combined with Erythromycin.Approved, Investigational, Vet Approved
EscitalopramThe risk or severity of hypotension can be increased when Escitalopram is combined with Loperamide.Approved, Investigational
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Loperamide.Approved
FelodipineThe metabolism of Loperamide can be decreased when combined with Felodipine.Approved, Investigational
FenticonazoleThe therapeutic efficacy of Fenticonazole can be increased when used in combination with Loperamide.Experimental
FluconazoleThe metabolism of Loperamide can be decreased when combined with Fluconazole.Approved, Investigational
FlucytosineThe therapeutic efficacy of Flucytosine can be increased when used in combination with Loperamide.Approved, Investigational
FluoxetineThe metabolism of Loperamide can be decreased when combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe risk or severity of hypotension can be increased when Flupentixol is combined with Loperamide.Approved, Investigational, Withdrawn
FlutrimazoleThe therapeutic efficacy of Flutrimazole can be increased when used in combination with Loperamide.Experimental
FluvoxamineThe metabolism of Loperamide can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Loperamide can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Loperamide can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Loperamide can be increased when combined with Fosphenytoin.Approved, Investigational
Fusidic AcidThe serum concentration of Loperamide can be increased when it is combined with Fusidic Acid.Approved, Investigational
GlyphosateThe therapeutic efficacy of Glyphosate can be increased when used in combination with Loperamide.Experimental
GriseofulvinThe therapeutic efficacy of Griseofulvin can be increased when used in combination with Loperamide.Approved, Investigational, Vet Approved
HachimycinThe therapeutic efficacy of Hachimycin can be increased when used in combination with Loperamide.Experimental
HaloperidolThe metabolism of Loperamide can be decreased when combined with Haloperidol.Approved
HaloproginThe therapeutic efficacy of Haloprogin can be increased when used in combination with Loperamide.Approved, Withdrawn
HexetidineThe therapeutic efficacy of Hexetidine can be increased when used in combination with Loperamide.Approved, Investigational
HexobarbitalThe metabolism of Loperamide can be increased when combined with Hexobarbital.Approved
IdelalisibThe metabolism of Loperamide can be decreased when combined with Idelalisib.Approved
IloperidoneThe risk or severity of hypotension can be increased when Iloperidone is combined with Loperamide.Approved
ImatinibThe metabolism of Loperamide can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Loperamide can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Loperamide can be decreased when combined with Indinavir.Approved
IndoraminThe risk or severity of hypotension can be increased when Indoramin is combined with Loperamide.Withdrawn
IrbesartanThe metabolism of Loperamide can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoleThe serum concentration of Loperamide can be increased when it is combined with Isavuconazole.Approved, Investigational
IsavuconazoniumThe metabolism of Loperamide can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoconazoleThe therapeutic efficacy of Isoconazole can be increased when used in combination with Loperamide.Approved
IsoniazidThe metabolism of Loperamide can be decreased when combined with Isoniazid.Approved, Investigational
IsradipineThe metabolism of Loperamide can be decreased when combined with Isradipine.Approved, Investigational
ItraconazoleThe metabolism of Loperamide can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Loperamide can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Loperamide can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolThe risk or severity of hypotension can be increased when Labetalol is combined with Loperamide.Approved
LapatinibThe metabolism of Loperamide can be decreased when combined with Lapatinib.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Loperamide.Approved
LisdexamfetamineThe risk or severity of hypotension can be increased when Lisdexamfetamine is combined with Loperamide.Approved, Investigational
LopinavirThe metabolism of Loperamide can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Loperamide can be decreased when combined with Lorcaserin.Approved
LorpiprazoleThe serum concentration of Loperamide can be increased when it is combined with Lorpiprazole.Approved
LosartanThe metabolism of Loperamide can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Loperamide can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Loperamide can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Loperamide can be increased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Loperamide can be decreased when combined with Lumefantrine.Approved
Magnesium hydroxideThe risk or severity of hypotension and neuromuscular blockade can be increased when Loperamide is combined with Magnesium hydroxide.Approved, Investigational
Magnesium oxideThe risk or severity of hypotension and neuromuscular blockade can be increased when Loperamide is combined with Magnesium oxide.Approved
Magnesium salicylateThe risk or severity of hypotension and neuromuscular blockade can be increased when Loperamide is combined with Magnesium salicylate.Approved
Magnesium sulfateThe risk or severity of hypotension and neuromuscular blockade can be increased when Loperamide is combined with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe metabolism of Loperamide can be decreased when combined with Manidipine.Approved, Investigational
MepartricinThe therapeutic efficacy of Mepartricin can be increased when used in combination with Loperamide.Experimental
MethadoneThe metabolism of Loperamide can be decreased when combined with Methadone.Approved
MethohexitalThe metabolism of Loperamide can be increased when combined with Methohexital.Approved
MethotrimeprazineThe metabolism of Loperamide can be decreased when combined with Methotrimeprazine.Approved, Investigational
MethylphenobarbitalThe metabolism of Loperamide can be increased when combined with Methylphenobarbital.Approved
MetoprololThe metabolism of Loperamide can be decreased when combined with Metoprolol.Approved, Investigational
MevastatinThe therapeutic efficacy of Mevastatin can be increased when used in combination with Loperamide.Experimental
MicafunginThe therapeutic efficacy of Micafungin can be increased when used in combination with Loperamide.Approved, Investigational
MiconazoleThe therapeutic efficacy of Miconazole can be increased when used in combination with Loperamide.Approved, Investigational, Vet Approved
MidostaurinThe metabolism of Loperamide can be decreased when combined with Midostaurin.Approved, Investigational
MifepristoneThe serum concentration of Loperamide can be increased when it is combined with Mifepristone.Approved, Investigational
MiltefosineThe therapeutic efficacy of Miltefosine can be increased when used in combination with Loperamide.Approved, Investigational
MirabegronThe metabolism of Loperamide can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Loperamide can be decreased when it is combined with Mitotane.Approved
MonensinThe therapeutic efficacy of Monensin can be increased when used in combination with Loperamide.Vet Approved
MyxothiazolThe therapeutic efficacy of Myxothiazol can be increased when used in combination with Loperamide.Experimental
NabiloneThe metabolism of Loperamide can be decreased when combined with Nabilone.Approved, Investigational
NafcillinThe therapeutic efficacy of Loperamide can be decreased when used in combination with Nafcillin.Approved, Investigational
NaftifineThe therapeutic efficacy of Naftifine can be increased when used in combination with Loperamide.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Loperamide.Approved
NatamycinThe therapeutic efficacy of Natamycin can be increased when used in combination with Loperamide.Approved
NefazodoneThe metabolism of Loperamide can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Loperamide can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Loperamide can be increased when it is combined with Netupitant.Approved, Investigational
NevirapineThe metabolism of Loperamide can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Loperamide can be decreased when combined with Nicardipine.Approved, Investigational
NicergolineThe risk or severity of hypotension can be increased when Nicergoline is combined with Loperamide.Approved, Investigational
NifuratelThe therapeutic efficacy of Nifuratel can be increased when used in combination with Loperamide.Experimental
NiguldipineThe risk or severity of hypotension can be increased when Niguldipine is combined with Loperamide.Experimental
Nikkomycin ZThe therapeutic efficacy of Nikkomycin Z can be increased when used in combination with Loperamide.Investigational
NilotinibThe metabolism of Loperamide can be decreased when combined with Nilotinib.Approved, Investigational
NitroprussideLoperamide may increase the hypotensive activities of Nitroprusside.Approved, Investigational
NitroxolineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Loperamide.Approved
NortriptylineThe risk or severity of hypotension can be increased when Nortriptyline is combined with Loperamide.Approved
NystatinThe therapeutic efficacy of Nystatin can be increased when used in combination with Loperamide.Approved, Vet Approved
OlanzapineThe risk or severity of hypotension can be increased when Olanzapine is combined with Loperamide.Approved, Investigational
OlaparibThe metabolism of Loperamide can be decreased when combined with Olaparib.Approved
OmoconazoleThe therapeutic efficacy of Omoconazole can be increased when used in combination with Loperamide.Experimental
OsimertinibThe serum concentration of Loperamide can be increased when it is combined with Osimertinib.Approved
OxiconazoleThe therapeutic efficacy of Oxiconazole can be increased when used in combination with Loperamide.Approved
PafuramidineThe therapeutic efficacy of Pafuramidine can be increased when used in combination with Loperamide.Investigational
PalbociclibThe serum concentration of Loperamide can be increased when it is combined with Palbociclib.Approved, Investigational
PaliperidoneThe risk or severity of hypotension can be increased when Paliperidone is combined with Loperamide.Approved
PanobinostatThe serum concentration of Loperamide can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Loperamide can be decreased when combined with Paroxetine.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Loperamide.Approved
Peginterferon alfa-2bThe serum concentration of Loperamide can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentamidineThe therapeutic efficacy of Pentamidine can be increased when used in combination with Loperamide.Approved, Investigational
PentobarbitalThe metabolism of Loperamide can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PhenobarbitalThe metabolism of Loperamide can be increased when combined with Phenobarbital.Approved, Investigational
PhenoxybenzamineThe risk or severity of hypotension can be increased when Phenoxybenzamine is combined with Loperamide.Approved
PhentolamineThe risk or severity of hypotension can be increased when Phentolamine is combined with Loperamide.Approved
PhenytoinThe metabolism of Loperamide can be increased when combined with Phenytoin.Approved, Vet Approved
PioglitazoneThe metabolism of Loperamide can be decreased when combined with Pioglitazone.Approved, Investigational
PitolisantThe serum concentration of Loperamide can be decreased when it is combined with Pitolisant.Approved, Investigational
PizotifenThe risk or severity of hypotension can be increased when Pizotifen is combined with Loperamide.Approved
PosaconazoleThe metabolism of Loperamide can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrazosinThe risk or severity of hypotension can be increased when Prazosin is combined with Loperamide.Approved
PrimidoneThe metabolism of Loperamide can be increased when combined with Primidone.Approved, Vet Approved
PromazineThe metabolism of Loperamide can be decreased when combined with Promazine.Approved, Vet Approved
PropericiazineThe risk or severity of hypotension can be increased when Propericiazine is combined with Loperamide.Approved, Investigational
PropiomazineThe risk or severity of hypotension can be increased when Propiomazine is combined with Loperamide.Approved
PropiverineThe risk or severity of hypotension can be increased when Propiverine is combined with Loperamide.Approved, Investigational
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Loperamide.Approved
PyrrolnitrinThe therapeutic efficacy of Pyrrolnitrin can be increased when used in combination with Loperamide.Experimental
QuazepamThe serum concentration of Loperamide can be increased when it is combined with Quazepam.Approved, Illicit
QuetiapineThe risk or severity of hypotension can be increased when Quetiapine is combined with Loperamide.Approved
QuinidineThe metabolism of Loperamide can be decreased when combined with Quinidine.Approved, Investigational
QuinineThe metabolism of Loperamide can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Loperamide can be decreased when combined with Rabeprazole.Approved, Investigational
RacepinephrineThe risk or severity of hypotension can be increased when Racepinephrine is combined with Loperamide.Approved
RadicicolThe therapeutic efficacy of Radicicol can be increased when used in combination with Loperamide.Experimental
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Loperamide.Approved, Investigational
RifabutinThe metabolism of Loperamide can be increased when combined with Rifabutin.Approved, Investigational
RifampicinThe metabolism of Loperamide can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Loperamide can be increased when combined with Rifapentine.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Loperamide.Approved, Investigational
RisperidoneThe risk or severity of hypotension can be increased when Risperidone is combined with Loperamide.Approved, Investigational
RitonavirThe metabolism of Loperamide can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Loperamide can be decreased when combined with Rolapitant.Approved, Investigational
RopiniroleThe metabolism of Loperamide can be decreased when combined with Ropinirole.Approved, Investigational
RosiglitazoneThe metabolism of Loperamide can be decreased when combined with Rosiglitazone.Approved, Investigational
RucaparibThe metabolism of Loperamide can be decreased when combined with Rucaparib.Approved, Investigational
Salicylhydroxamic AcidThe therapeutic efficacy of Salicylhydroxamic Acid can be increased when used in combination with Loperamide.Experimental
Salicylic acidThe therapeutic efficacy of Salicylic acid can be increased when used in combination with Loperamide.Approved, Investigational, Vet Approved
SaquinavirThe metabolism of Loperamide can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Loperamide can be decreased when used in combination with Sarilumab.Approved, Investigational
SecobarbitalThe metabolism of Loperamide can be increased when combined with Secobarbital.Approved, Vet Approved
SertaconazoleThe therapeutic efficacy of Sertaconazole can be increased when used in combination with Loperamide.Approved, Investigational
SertralineThe metabolism of Loperamide can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Loperamide can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Loperamide.Approved
SiltuximabThe serum concentration of Loperamide can be decreased when it is combined with Siltuximab.Approved, Investigational
SimeprevirThe serum concentration of Loperamide can be increased when it is combined with Simeprevir.Approved
SinefunginThe therapeutic efficacy of Sinefungin can be increased when used in combination with Loperamide.Experimental
SirolimusThe therapeutic efficacy of Sirolimus can be increased when used in combination with Loperamide.Approved, Investigational
SorafenibThe metabolism of Loperamide can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Loperamide can be decreased when it is combined with St. John's Wort.Approved, Investigational, Nutraceutical
StiripentolThe serum concentration of Loperamide can be increased when it is combined with Stiripentol.Approved
SulconazoleThe therapeutic efficacy of Sulconazole can be increased when used in combination with Loperamide.Approved
SulfamethoxazoleThe metabolism of Loperamide can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Loperamide can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TamoxifenThe metabolism of Loperamide can be decreased when combined with Tamoxifen.Approved
TamsulosinThe risk or severity of hypotension can be increased when Tamsulosin is combined with Loperamide.Approved, Investigational
TavaboroleThe therapeutic efficacy of Tavaborole can be increased when used in combination with Loperamide.Approved, Investigational
TelaprevirThe metabolism of Loperamide can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Loperamide can be decreased when combined with Telithromycin.Approved
TerazosinThe risk or severity of hypotension can be increased when Terazosin is combined with Loperamide.Approved
TerbinafineThe metabolism of Loperamide can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TerconazoleThe therapeutic efficacy of Terconazole can be increased when used in combination with Loperamide.Approved
TeriflunomideThe metabolism of Loperamide can be decreased when combined with Teriflunomide.Approved
ThiamylalThe metabolism of Loperamide can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Loperamide can be increased when combined with Thiopental.Approved, Vet Approved
ThioproperazineThe risk or severity of hypotension can be increased when Thioproperazine is combined with Loperamide.Approved
ThioridazineThe metabolism of Loperamide can be decreased when combined with Thioridazine.Approved, Withdrawn
ThiotepaThe metabolism of Loperamide can be decreased when combined with Thiotepa.Approved, Investigational
ThymolThe therapeutic efficacy of Thymol can be increased when used in combination with Loperamide.Approved
TiclopidineThe metabolism of Loperamide can be decreased when combined with Ticlopidine.Approved
TioconazoleThe therapeutic efficacy of Tioconazole can be increased when used in combination with Loperamide.Approved
TipranavirThe metabolism of Loperamide can be decreased when combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Loperamide can be decreased when it is combined with Tocilizumab.Approved
TolazolineThe risk or severity of hypotension can be increased when Tolazoline is combined with Loperamide.Approved, Vet Approved
TolciclateThe therapeutic efficacy of Tolciclate can be increased when used in combination with Loperamide.Experimental
TolnaftateThe therapeutic efficacy of Tolnaftate can be increased when used in combination with Loperamide.Approved, Investigational, Vet Approved
TopiroxostatThe metabolism of Loperamide can be decreased when combined with Topiroxostat.Approved, Investigational
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Loperamide.Approved, Investigational
TranylcypromineThe metabolism of Loperamide can be decreased when combined with Tranylcypromine.Approved, Investigational
TrazodoneThe risk or severity of hypotension can be increased when Trazodone is combined with Loperamide.Approved, Investigational
TrifluoperazineThe risk or severity of hypotension can be increased when Trifluoperazine is combined with Loperamide.Approved, Investigational
TrimazosinThe risk or severity of hypotension can be increased when Trimazosin is combined with Loperamide.Experimental
TrimethoprimThe metabolism of Loperamide can be decreased when combined with Trimethoprim.Approved, Vet Approved
TrimetrexateThe therapeutic efficacy of Trimetrexate can be increased when used in combination with Loperamide.Approved, Investigational
TrimipramineThe risk or severity of hypotension can be increased when Trimipramine is combined with Loperamide.Approved
UrapidilThe risk or severity of hypotension can be increased when Urapidil is combined with Loperamide.Investigational
VemurafenibThe serum concentration of Loperamide can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Loperamide can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Loperamide can be decreased when combined with Verapamil.Approved
VincristineThe excretion of Vincristine can be decreased when combined with Loperamide.Approved, Investigational
VoriconazoleThe metabolism of Loperamide can be decreased when combined with Voriconazole.Approved, Investigational
WortmanninThe therapeutic efficacy of Wortmannin can be increased when used in combination with Loperamide.Experimental
ZiprasidoneThe metabolism of Loperamide can be decreased when combined with Ziprasidone.Approved
ZuclopenthixolThe risk or severity of hypotension can be increased when Zuclopenthixol is combined with Loperamide.Approved, Investigational
Food Interactions
  • Take without regard to meals. Increase liquid intake.

References

Synthesis Reference

Tsutomu Awamura, Hisanobu Nishikawa, Toshio Inagi, "FILM PREPARATION CONTAINING LOPERAMIDE HYDROCHLORIDE." U.S. Patent US20110159058, issued June 30, 2011.

US20110159058
General References
Not Available
External Links
Human Metabolome Database
HMDB0004999
KEGG Drug
D08144
KEGG Compound
C07080
PubChem Compound
3955
PubChem Substance
46504591
ChemSpider
3818
BindingDB
50017698
ChEBI
6532
ChEMBL
CHEMBL841
Therapeutic Targets Database
DAP000425
PharmGKB
PA450262
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Loperamide
ATC Codes
A07DA53 — Loperamide, combinationsA07DA03 — LoperamideA07DA05 — Loperamide oxide
AHFS Codes
  • 56:08.00 — Antidiarrhea Agents
FDA label
Download (55.5 KB)
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentPain1
1CompletedBasic ScienceDrug Interactions1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceIntestinal Obstruction2
1CompletedTreatmentHealthy Volunteers2
1RecruitingTreatmentNeoplasms, Breast1
2CompletedTreatmentCancer, Breast / Early-Stage Breast Carcinoma / Hormone Receptor Positive Tumor1
2RecruitingTreatmentEarly Stage HER2+ Breast Cancer1
2RecruitingTreatmentHer2-Positive Breast Cancer1
2WithdrawnTreatmentCancers1
2, 3CompletedTreatmentDiarrhea-predominant Irritable Bowel Syndrome / Functional Diarrhea1
2, 3CompletedTreatmentFemale Genital Diseases1
2, 3CompletedTreatmentIncontinence, Fecal1
2, 3Not Yet RecruitingTreatmentClostridium Difficile Infection (CDI)1
3CompletedSupportive CareColorectal Cancers / Diarrhea1
3CompletedTreatmentDiarrhea1
3CompletedTreatmentIncontinence, Fecal1
3CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
3TerminatedPreventionDehydration, Diverting Ileostomy, Loperamide1
3TerminatedPreventionDiarrhea1
3TerminatedTreatmentCancers / Diarrhea / Enteritis1
3TerminatedTreatmentHigh Output Stoma1
3TerminatedTreatmentRectal Carcinoma / Short Bowel Syndrome (SBS) / Ulcerative Colitis (UC)1
4CompletedTreatmentDiarrhea3
4CompletedTreatmentTravelers' Diarrhea1
4RecruitingTreatmentOpiate withdrawal symptoms1
4SuspendedTreatmentAntibiotic Associated Diarrhea / Antibiotic-Associated Diarrhea / Clostridium Difficile1
4TerminatedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
4WithdrawnTreatmentIncontinence, Fecal1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedTreatmentIncontinence, Fecal1
Not AvailableNot Yet RecruitingBasic ScienceIntestinal Transit1
Not AvailableRecruitingTreatmentIncontinence, Fecal1
Not AvailableTerminatedTreatmentIncontinence, Fecal1

Pharmacoeconomics

Manufacturers
  • Mcneil consumer healthcare
  • Mcneil pediatrics
  • Janssen pharmaceutica products lp
Packagers
  • Advanced Pharmaceutical Services Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Cardinal Health
  • Chain Drug
  • Chattem Chemicals Inc.
  • Comprehensive Consultant Services Inc.
  • CVS Pharmacy
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Heartland Repack Services LLC
  • Janssen-Ortho Inc.
  • Lake Chemicals Pvt Ltd.
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • McNeil Laboratories
  • Medique Products
  • Medisca Inc.
  • Mylan
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Qualitest
  • Redpharm Drug
  • Remedy Repack
  • Rugby Laboratories
  • Sandhills Packaging Inc.
  • Teva Pharmaceutical Industries Ltd.
  • Tya Pharmaceuticals
  • UDL Laboratories
  • Vangard Labs Inc.
Dosage forms
FormRouteStrength
SolutionOral1 mg/5mL
Capsule, liquid filledOral2 mg/1
KitOral
SolutionOral.2 mg
LiquidOral1 mg/5mL
Tablet, film coatedOral2 mg/1
SolutionOral1 mg/7.5mL
Tablet, coatedOral2 mg/1
SolutionOral2 mg
TabletOral
Tablet, chewableOral
CapsuleOral2 mg
LiquidOral.2 mg
CapsuleOral2 mg/1
LiquidOral1 mg/7.5mL
SolutionOral2 mg/10mL
SuspensionOral1 mg/7.5mL
TabletOral2 mg
SolutionOral0.2 mg
TabletOral2 mg/1
Prices
Unit descriptionCostUnit
Loperamide hcl powder26.01USD g
Loperamide HCl 2 mg capsule0.64USD capsule
Imodium a-d 2 mg caplet0.49USD caplet
Imodium advanced caplet0.46USD caplet
Imodium ms relief caplet0.46USD caplet
Kaopectate 262 mg caplet0.37USD caplet
Loperamide 2 mg caplet0.37USD caplet
Qc anti-diarrheal adv caplet0.3USD caplet
Diamode 2 mg tablet0.28USD tablet
Kaopectate 240 mg softgel0.25USD softgel capsule
Anti-diarrheal 2 mg caplet0.18USD caplet
CVS Pharmacy anti-diarrheal 2 mg caplet0.14USD caplet
Kaopectate children's suspension0.02USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2134611No2002-12-242014-10-28Canada
US6814978Yes2002-02-262022-02-26Us
US6103260No1997-07-172017-07-17Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)222.1U.S. Patent 3,714,159; 3,884,916.
water solubilitySlightNot Available
logP5.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00086 mg/mLALOGPS
logP4.44ALOGPS
logP4.77ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)13.96ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.78 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity139.32 m3·mol-1ChemAxon
Polarizability52.67 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9878
Blood Brain Barrier+0.7709
Caco-2 permeable+0.5875
P-glycoprotein substrateSubstrate0.7476
P-glycoprotein inhibitor IInhibitor0.8277
P-glycoprotein inhibitor IIInhibitor0.8387
Renal organic cation transporterInhibitor0.5059
CYP450 2C9 substrateNon-substrate0.8057
CYP450 2D6 substrateNon-substrate0.5315
CYP450 3A4 substrateSubstrate0.7918
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9154
CYP450 2D6 inhibitorInhibitor0.8933
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9207
Ames testNon AMES toxic0.768
CarcinogenicityNon-carcinogens0.8564
BiodegradationNot ready biodegradable0.9953
Rat acute toxicity3.6560 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9461
hERG inhibition (predictor II)Inhibitor0.7639
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-004i-0000900000-673950710672b433271c
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-014i-0090000000-4b7b347a8b8e9dca406c
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-02t9-0090000000-31f15df976e23e73330a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-004i-0000900000-d91d13c4e4665bd5fb5a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-004i-0020900000-f1be3181a6918c985ffd
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-014i-0090000000-e5e41346303f41f65688
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014i-0090000000-acd8b87c1338e5d0fe25
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-0090000000-81b85f788d14641430fd
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-014i-0090000000-3ce1a89454d777268799
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-03di-0090000000-f101d63ad0bf8e5d2178
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-0000900000-d91d13c4e4665bd5fb5a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-0020900000-f1be3181a6918c985ffd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0090000000-e5e41346303f41f65688
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0090000000-acd8b87c1338e5d0fe25
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0090000000-81b85f788d14641430fd
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-014i-0090000000-1a1a49f09397ad090e82
MS/MS Spectrum - , positiveLC-MS/MSsplash10-016r-0090600000-794ea6214c0cd97c73fa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-016r-0090300000-e11942e343a28799a5ab
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Phenylpiperidines / Phenylacetamides / Aralkylamines / Chlorobenzenes / Aryl chlorides / N-acyl amines / Tertiary carboxylic acid amides / Tertiary alcohols / Trialkylamines / Amino acids and derivatives
show 6 more
Substituents
Diphenylmethane / Phenylpiperidine / Phenylacetamide / Chlorobenzene / Aralkylamine / Halobenzene / Aryl chloride / Aryl halide / Piperidine / N-acyl-amine
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, tertiary alcohol, monocarboxylic acid amide, monochlorobenzenes (CHEBI:6532)

Targets

Details
1. Mu-type opioid receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. DeHaven-Hudkins DL, Burgos LC, Cassel JA, Daubert JD, DeHaven RN, Mansson E, Nagasaka H, Yu G, Yaksh T: Loperamide (ADL 2-1294), an opioid antihyperalgesic agent with peripheral selectivity. J Pharmacol Exp Ther. 1999 Apr;289(1):494-502. [PubMed:10087042]
  2. Tan-No K, Niijima F, Nakagawasai O, Sato T, Satoh S, Tadano T: Development of tolerance to the inhibitory effect of loperamide on gastrointestinal transit in mice. Eur J Pharm Sci. 2003 Nov;20(3):357-63. [PubMed:14592702]
  3. Roge J, Baumer P, Berard H, Schwartz JC, Lecomte JM: The enkephalinase inhibitor, acetorphan, in acute diarrhoea. A double-blind, controlled clinical trial versus loperamide. Scand J Gastroenterol. 1993 Apr;28(4):352-4. [PubMed:8488368]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  5. Giagnoni G, Casiraghi L, Senini R, Revel L, Parolaro D, Sala M, Gori E: Loperamide: evidence of interaction with mu and delta opioid receptors. Life Sci. 1983;33 Suppl 1:315-8. [PubMed:6319884]
  6. di Bosco AM, Grieco P, Diurno MV, Campiglia P, Novellino E, Mazzoni O: Binding site of loperamide: automated docking of loperamide in human mu- and delta-opioid receptors. Chem Biol Drug Des. 2008 Apr;71(4):328-35. doi: 10.1111/j.1747-0285.2008.00637.x. Epub 2008 Feb 12. [PubMed:18284554]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Giagnoni G, Casiraghi L, Senini R, Revel L, Parolaro D, Sala M, Gori E: Loperamide: evidence of interaction with mu and delta opioid receptors. Life Sci. 1983;33 Suppl 1:315-8. [PubMed:6319884]
  3. di Bosco AM, Grieco P, Diurno MV, Campiglia P, Novellino E, Mazzoni O: Binding site of loperamide: automated docking of loperamide in human mu- and delta-opioid receptors. Chem Biol Drug Des. 2008 Apr;71(4):328-35. doi: 10.1111/j.1747-0285.2008.00637.x. Epub 2008 Feb 12. [PubMed:18284554]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. DeHaven-Hudkins DL, Burgos LC, Cassel JA, Daubert JD, DeHaven RN, Mansson E, Nagasaka H, Yu G, Yaksh T: Loperamide (ADL 2-1294), an opioid antihyperalgesic agent with peripheral selectivity. J Pharmacol Exp Ther. 1999 Apr;289(1):494-502. [PubMed:10087042]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated calcium channel activity
Specific Function
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hor...
Gene Name
CACNA1A
Uniprot ID
O00555
Uniprot Name
Voltage-dependent P/Q-type calcium channel subunit alpha-1A
Molecular Weight
282362.39 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Church J, Fletcher EJ, Abdel-Hamid K, MacDonald JF: Loperamide blocks high-voltage-activated calcium channels and N-methyl-D-aspartate-evoked responses in rat and mouse cultured hippocampal pyramidal neurons. Mol Pharmacol. 1994 Apr;45(4):747-57. [PubMed:8183255]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Modulator
General Function
Type 4 melanocortin receptor binding
Specific Function
ACTH stimulates the adrenal glands to release cortisol.MSH (melanocyte-stimulating hormone) increases the pigmentation of skin by increasing melanin production in melanocytes.Beta-endorphin and Met...
Gene Name
POMC
Uniprot ID
P01189
Uniprot Name
Pro-opiomelanocortin
Molecular Weight
29423.72 Da
References
  1. Nomura A, Iwasaki Y, Aoki Y, Yamamori E, Mutsuga N, Yoshida M, Asai M, Oiso Y, Saito H: Effects of loperamide and other opioid-related substances on the transcriptional regulation of the rat pro-opiomelanocortin gene in AtT20 cells. Neuroendocrinology. 2001 Aug;74(2):87-94. [PubMed:11474216]
  2. Auernhammer CJ, Stalla GK, Lange M, Pfeiffer A, Muller OA: Effects of loperamide on the human hypothalamo-pituitary-adrenal axis in vivo and in vitro. J Clin Endocrinol Metab. 1992 Aug;75(2):552-7. [PubMed:1322429]
  3. Ambrosi B, Bochicchio D, Ferrario R, Colombo P, Faglia G: Effects of the opiate agonist loperamide on pituitary-adrenal function in patients with suspected hypercortisolism. J Endocrinol Invest. 1989 Jan;12(1):31-5. [PubMed:2545766]
  4. Ambrosi B, Bochicchio D, Colombo P, Ferrario R, Faglia G: Loperamide modifies but does not block the corticotropin-releasing hormone-induced ACTH response in patients with Addison's disease. Horm Metab Res Suppl. 1987;16:74-5. [PubMed:2832297]
  5. Bochicchio D, Ambrosi B, Faglia G: Loperamide, an opiate analog, differently modifies the adrenocorticotropin responses to corticotropin-releasing hormone and lysine vasopressin in patients with Addison's disease. Neuroendocrinology. 1988 Dec;48(6):611-4. [PubMed:2855105]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Titin binding
Specific Function
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number...
Gene Name
CALM1
Uniprot ID
P0DP23
Uniprot Name
Calmodulin
Molecular Weight
16837.47 Da
References
  1. Daly JW, Harper J: Loperamide: novel effects on capacitative calcium influx. Cell Mol Life Sci. 2000 Jan 20;57(1):149-57. [PubMed:10949586]
  2. Suzuki T, Sakai H, Ikari A, Takeguchi N: Inhibition of thromboxane A(2)-induced Cl(-) secretion by antidiarrhea drug loperamide in isolated rat colon. J Pharmacol Exp Ther. 2000 Oct;295(1):233-8. [PubMed:10991984]
  3. Mellstrand T: Loperamide--an opiate receptor agonist with gastrointestinal motility effects. Scand J Gastroenterol Suppl. 1987;130:65-6. [PubMed:2820051]
  4. Stoll R, Ruppin H, Domschke W: Calmodulin-mediated effects of loperamide on chloride transport by brush border membrane vesicles from human ileum. Gastroenterology. 1988 Jul;95(1):69-76. [PubMed:2836258]
  5. Diener M, Knobloch SF, Rummel W: Action of loperamide on neuronally mediated and Ca2+- or cAMP-mediated secretion in rat colon. Eur J Pharmacol. 1988 Aug 2;152(3):217-25. [PubMed:2851449]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Curator comments
Inverse agonist at the canonical form of the receptor. Likely an antagonist at isoform 3 of the receptor.
General Function
Zinc ion binding
Specific Function
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
Gene Name
NR1I3
Uniprot ID
Q14994
Uniprot Name
Nuclear receptor subfamily 1 group I member 3
Molecular Weight
39942.145 Da
References
  1. Dring AM, Anderson LE, Qamar S, Stoner MA: Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. Chem Biol Interact. 2010 Dec 5;188(3):512-25. doi: 10.1016/j.cbi.2010.09.018. Epub 2010 Oct 20. [PubMed:20869355]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Baker DE: Loperamide: a pharmacological review. Rev Gastroenterol Disord. 2007;7 Suppl 3:S11-8. [PubMed:18192961]
  2. Kim KA, Chung J, Jung DH, Park JY: Identification of cytochrome P450 isoforms involved in the metabolism of loperamide in human liver microsomes. Eur J Clin Pharmacol. 2004 Oct;60(8):575-81. Epub 2004 Sep 8. [PubMed:15365656]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Kim KA, Chung J, Jung DH, Park JY: Identification of cytochrome P450 isoforms involved in the metabolism of loperamide in human liver microsomes. Eur J Clin Pharmacol. 2004 Oct;60(8):575-81. Epub 2004 Sep 8. [PubMed:15365656]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Kim KA, Chung J, Jung DH, Park JY: Identification of cytochrome P450 isoforms involved in the metabolism of loperamide in human liver microsomes. Eur J Clin Pharmacol. 2004 Oct;60(8):575-81. Epub 2004 Sep 8. [PubMed:15365656]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Kim KA, Chung J, Jung DH, Park JY: Identification of cytochrome P450 isoforms involved in the metabolism of loperamide in human liver microsomes. Eur J Clin Pharmacol. 2004 Oct;60(8):575-81. Epub 2004 Sep 8. [PubMed:15365656]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Wandel C, Kim R, Wood M, Wood A: Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein. Anesthesiology. 2002 Apr;96(4):913-20. [PubMed:11964599]
  2. Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [PubMed:11785684]
  3. Schinkel AH, Wagenaar E, Mol CA, van Deemter L: P-glycoprotein in the blood-brain barrier of mice influences the brain penetration and pharmacological activity of many drugs. J Clin Invest. 1996 Jun 1;97(11):2517-24. [PubMed:8647944]

Drug created on June 13, 2005 07:24 / Updated on July 19, 2018 17:50