Details
Stereochemistry | ACHIRAL |
Molecular Formula | C29H33ClN2O2 |
Molecular Weight | 477.038 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C(=O)C(CCN1CCC(O)(CC1)C2=CC=C(Cl)C=C2)(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=RDOIQAHITMMDAJ-UHFFFAOYSA-N
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
Loperamide is a commonly used over-the-counter (OTC) and prescription medicine that is approved to help control symptoms of diarrhea, including Travelers’ Diarrhea. The maximum approved daily dose for adults is 8 mg per day for OTC use and 16 mg per day for prescription use. It is sold under the OTC brand name Imodium A-D, as store brands, and as generics. In vitro and animal studies show that IMODIUM® (loperamide hydrochloride) acts by slowing
intestinal motility and by affecting water and electrolyte movement through the bowel.
Loperamide binds to the opiate receptor in the gut wall. Consequently, it inhibits the release of
acetylcholine and prostaglandins, thereby reducing propulsive peristalsis, and increasing
intestinal transit time. Loperamide increases the tone of the anal sphincter, thereby reducing incontinence and urgency. 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.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27918873
Curator's Comment: Loperamide was first synthesized by Paul Janssen of Janssen Pharmaceutica in 1969
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.24 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/438356 |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOPERAMIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
26.1 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/438356 |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOPERAMIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/438356 |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOPERAMIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.8 h |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOPERAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% |
4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered: |
LOPERAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
400 mg 2 times / day multiple, oral Overdose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 26 Sex: M Population Size: 1 Sources: |
Disc. AE: Cardiac arrest... AEs leading to discontinuation/dose reduction: Cardiac arrest (grade 5) Sources: |
792 mg 1 times / day multiple, oral (total daily dose) Overdose Dose: 792 mg, 1 times / day Route: oral Route: multiple Dose: 792 mg, 1 times / day Sources: Page: p.954 |
unhealthy, 28 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.954 |
Disc. AE: Syncope, Tachycardia... AEs leading to discontinuation/dose reduction: Syncope Sources: Page: p.954Tachycardia Electrocardiogram QTc interval prolonged Cardiac arrest |
400 mg 1 times / day multiple, oral Overdose Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 30 Sex: M Population Size: 1 Sources: |
Disc. AE: Syncope, Cardiac arrest... AEs leading to discontinuation/dose reduction: Syncope Sources: Cardiac arrest Torsades de pointes |
16 mg 8 times / day multiple, oral (total daily dose) Recommended Dose: 16 mg, 8 times / day Route: oral Route: multiple Dose: 16 mg, 8 times / day Sources: Page: p.1, 3 |
unhealthy Health Status: unhealthy Condition: Diarrhea Sources: Page: p.1, 3 |
Disc. AE: Torsades de pointes, Cardiac arrest... AEs leading to discontinuation/dose reduction: Torsades de pointes Sources: Page: p.1, 3Cardiac arrest |
16 mg 8 times / day multiple, oral (total daily dose) Recommended Dose: 16 mg, 8 times / day Route: oral Route: multiple Dose: 16 mg, 8 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Diarrhea Sources: Page: p.3 |
Disc. AE: Ventricular tachycardia, Syncope... AEs leading to discontinuation/dose reduction: Ventricular tachycardia Sources: Page: p.3Syncope |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Cardiac arrest | grade 5 Disc. AE |
400 mg 2 times / day multiple, oral Overdose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy, 26 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 26 Sex: M Population Size: 1 Sources: |
Cardiac arrest | Disc. AE | 792 mg 1 times / day multiple, oral (total daily dose) Overdose Dose: 792 mg, 1 times / day Route: oral Route: multiple Dose: 792 mg, 1 times / day Sources: Page: p.954 |
unhealthy, 28 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.954 |
Electrocardiogram QTc interval prolonged | Disc. AE | 792 mg 1 times / day multiple, oral (total daily dose) Overdose Dose: 792 mg, 1 times / day Route: oral Route: multiple Dose: 792 mg, 1 times / day Sources: Page: p.954 |
unhealthy, 28 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.954 |
Syncope | Disc. AE | 792 mg 1 times / day multiple, oral (total daily dose) Overdose Dose: 792 mg, 1 times / day Route: oral Route: multiple Dose: 792 mg, 1 times / day Sources: Page: p.954 |
unhealthy, 28 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.954 |
Tachycardia | Disc. AE | 792 mg 1 times / day multiple, oral (total daily dose) Overdose Dose: 792 mg, 1 times / day Route: oral Route: multiple Dose: 792 mg, 1 times / day Sources: Page: p.954 |
unhealthy, 28 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.954 |
Cardiac arrest | Disc. AE | 400 mg 1 times / day multiple, oral Overdose Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 30 Sex: M Population Size: 1 Sources: |
Syncope | Disc. AE | 400 mg 1 times / day multiple, oral Overdose Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 30 Sex: M Population Size: 1 Sources: |
Torsades de pointes | Disc. AE | 400 mg 1 times / day multiple, oral Overdose Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, 30 n = 1 Health Status: unhealthy Condition: Opiate abuse Age Group: 30 Sex: M Population Size: 1 Sources: |
Cardiac arrest | Disc. AE | 16 mg 8 times / day multiple, oral (total daily dose) Recommended Dose: 16 mg, 8 times / day Route: oral Route: multiple Dose: 16 mg, 8 times / day Sources: Page: p.1, 3 |
unhealthy Health Status: unhealthy Condition: Diarrhea Sources: Page: p.1, 3 |
Torsades de pointes | Disc. AE | 16 mg 8 times / day multiple, oral (total daily dose) Recommended Dose: 16 mg, 8 times / day Route: oral Route: multiple Dose: 16 mg, 8 times / day Sources: Page: p.1, 3 |
unhealthy Health Status: unhealthy Condition: Diarrhea Sources: Page: p.1, 3 |
Syncope | Disc. AE | 16 mg 8 times / day multiple, oral (total daily dose) Recommended Dose: 16 mg, 8 times / day Route: oral Route: multiple Dose: 16 mg, 8 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Diarrhea Sources: Page: p.3 |
Ventricular tachycardia | Disc. AE | 16 mg 8 times / day multiple, oral (total daily dose) Recommended Dose: 16 mg, 8 times / day Route: oral Route: multiple Dose: 16 mg, 8 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Diarrhea Sources: Page: p.3 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16415122/ Page: 1.0 |
strong [IC50 0.05 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 2.0 |
minor | |||
Page: 2.0 |
minor | |||
yes | ||||
Page: 2.0 |
yes | yes (co-administration study) Comment: single 4-mg dose of loperamide hydrochloride was co-administered with 600 mg gemfibrozil, a strong inhibitor of CYP2C8, on day 3 of a 5-day treatment with gemfibrozil twice daily, the mean peak plasma concentration and the systemic exposure to loperamide was increased by 1.6-fold and 2.2-fold, respectively Page: 2.0 |
||
Page: 2.0 |
yes | yes (co-administration study) Comment: Concomitant administration of multiple doses of 100 mg itraconazole twice daily, an inhibitor of both CYP3A4, with a single 4-mg dose of loperamide hydrochloride increased the peak plasma concentration and the systemic exposure to loperamide by 2.9-fold and 3.8-fold, respectively Page: 2.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Recent concepts in fecal incontinence. | 2001 Aug |
|
Intestinal cryptosporidiosis as an initial manifestation in a previously healthy Japanese patient with AIDS. | 2002 |
|
[Effect of jianpi wenshen decoction on serum gastrin, plasma motilin and somatostatin in patients of diabetic diarrhea]. | 2002 Aug |
|
Irinotecan in relapsed or refractory non-Hodgkin's lymphomas. Indications of activity in a phase II trial. | 2002 Aug |
|
A 'modified de Gramont' regimen of fluorouracil, alone and with oxaliplatin, for advanced colorectal cancer. | 2002 Aug 12 |
|
Acute gastroenteritis in children. | 2002 Dec |
|
Effects of full-thickness burns on nociceptor sensitization in anesthetized rats. | 2002 Dec |
|
Determination of the active ingredient loperamide hydrochloride in pharmaceutical caplets by high performance thin layer chromatography with ultraviolet absorption densitometry of fluorescence quenched zones. | 2002 Jan-Feb |
|
Irritable bowel syndrome: update on pathogenesis and management. | 2002 Jan-Mar |
|
Irritable bowel syndrome neuropharmacology. A review of approved and investigational compounds. | 2002 Jul |
|
Acute gastroenteritis in children. | 2002 Jun |
|
A multinational comparison of racecadotril and loperamide in the treatment of acute watery diarrhoea in adults. | 2002 Jun |
|
Laxative and anti-diarrheal activity of polycarbophil in mice and rats. | 2002 Jun |
|
Fumagillin treatment of intestinal microsporidiosis. | 2002 Jun 20 |
|
Short bowel syndrome: a nutritional and medical approach. | 2002 May 14 |
|
Systematic review on the management of irritable bowel syndrome in North America. | 2002 Nov |
|
Evidence-based position statement on the management of irritable bowel syndrome in North America. | 2002 Nov |
|
Lymphocytic colitis: clinical features, treatment, and outcomes. | 2002 Nov |
|
Spreading depression: imaging and blockade in the rat neocortical brain slice. | 2002 Nov |
|
Management of irritable bowel syndrome. | 2002 Nov 15 |
|
Phase I study of docetaxel in combination with cyclophosphamide as first-line chemotherapy for metastatic breast cancer. | 2002 Nov 4 |
|
Efficacy of prophylactic anti-diarrhoeal treatment in patients receiving Campto for advanced colorectal cancer. | 2002 Nov-Dec |
|
New developments in the diagnosis and treatment of irritable bowel syndrome. | 2002 Oct |
|
Antipruritic and antihyperalgesic actions of loperamide and analogs. | 2002 Oct 25 |
|
Irinotecan, cisplatin and mitomycin in inoperable gastro-oesophageal and pancreatic cancers - a new active regimen. | 2002 Oct 7 |
|
[Taking charge of adult's anal incontinence]. | 2002 Sep |
|
[Travellers' acute diarrhea]. | 2002 Sep |
|
Antidiarrhoeal activity of seed extract of Albizzia lebbeck Benth. | 2002 Sep |
|
Functional effects of systemically administered agonists and antagonists of mu, delta, and kappa opioid receptor subtypes on body temperature in mice. | 2002 Sep |
|
Dose-response relationship and mechanism of action of Saccharomyces boulardii in castor oil-induced diarrhea in rats. | 2003 Apr |
|
Effect of loperamide on gastro-oesophageal reflux. | 2003 Apr |
|
Pharmacologic therapy for the irritable bowel syndrome. | 2003 Apr |
|
Antidiarrhoeal activity of hot water extract of black tea (Camellia sinensis). | 2003 Apr |
|
Cost of illness in the 1993 waterborne Cryptosporidium outbreak, Milwaukee, Wisconsin. | 2003 Apr |
|
Irinotecan plus raltitrexed vs raltitrexed alone in patients with gemcitabine-pretreated advanced pancreatic adenocarcinoma. | 2003 Apr 22 |
|
[Ileus after the use of loperamide in a child with acute diarrhea]. | 2003 Apr 5 |
|
Morphine and d-amphetamine nullify each others' hypothermic effects in mice. | 2003 Feb |
|
Racecadotril versus loperamide: antidiarrheal research revisited. | 2003 Feb |
|
Lack of opioid or dopaminergic effects on unconditioned sexual incentive motivation in male rats. | 2003 Feb |
|
Travellers' diarrhoea. | 2003 Feb |
|
Evaluation of anti-diarrhoeal activity in seed extracts of Mangifera indica. | 2003 Jan |
|
Drug complexation, in vitro release and cellular entry of dendrimers and hyperbranched polymers. | 2003 Jun 18 |
|
Evaluation of different calorimetric methods to determine the glass transition temperature and molecular mobility below T(g) for amorphous drugs. | 2003 Jun 18 |
|
[Malaria--case report]. | 2003 Jun 6 |
|
EORTC Early Clinical Studies Group early phase II trial of S-1 in patients with advanced or metastatic colorectal cancer. | 2003 Mar 10 |
|
I get occasional diarrhea. Is there anything nonprescription that's particularly effective for that? | 2003 May |
|
Loperamide mobilizes intracellular Ca2+ stores in insulin-secreting HIT-T15 cells. | 2003 May |
|
Postinfectious irritable bowel syndrome. | 2003 May |
|
Suspicion of microscopic colitis raised by sonographic examination. | 2003 May |
|
Facilitation of drug entry into the CNS via transient permeation of blood brain barrier: laboratory and preliminary clinical evidence from bradykinin receptor agonist, Cereport. | 2003 May 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/loperamide.html
Usual Adult Dose for Diarrhea - Acute
Tablets, capsules, and liquid:
Initial: 4 mg orally after the first loose stool, then
Maintenance: 2 mg after each loose stool, not to exceed 16 mg in any 24-hour period. Clinical improvement is usually observed within 48 hours.
Chewable tablets:
Initial: 4 mg after the first loose stool, then
Maintenance: 2 mg after each subsequent loose stool, but not exceeding 8 mg in 24 hours.
Usual Adult Dose for Diarrhea - Chronic
Tablets, capsules, and liquid:
Initial: 4 mg orally once followed by 2 mg orally after each loose stool, not to exceed 16 mg in any 24-hour period.
Maintenance: The average daily maintenance dosage is 4 to 8 mg. Clinical improvement is usually observed within 10 days. If clinical improvement is not observed at a maximum dosage of 16 mg for duration of 10 days, symptoms are unlikely to be controlled by further administration.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11021978
Loperamide caused a concentration-dependent inhibition of the ascending contractile reflex response in the rat ileum with an IC(50) of 1.4x10(-7)M
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QA07DA03
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A07DA53
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A07DA03
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NCI_THESAURUS |
C1506
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NDF-RT |
N0000175690
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C266
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N0000000174
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NBK547935
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QA07DA53
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258-416-5
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)