Loperamide

Loperamide, sold under the brand name Imodium, among others, is a medication of the opioid receptor agonist class used to decrease the frequency of diarrhea. It is often used for this purpose in irritable bowel syndrome, inflammatory bowel disease and short bowel syndrome. It is not recommended for those with blood in the stool, mucus in the stool, or fevers. The medication is taken by mouth.

Loperamide
Clinical data
Pronunciation/loʊˈpɛrəmaɪd/
Trade namesImodium, others
Other namesR-18553, Loperamide hydrochloride (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa682280
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability0.3%
Protein binding97%
MetabolismLiver (extensive)
Elimination half-life9–14 hours
ExcretionFeces (30–40%), urine (1%)
Identifiers
  • 4-[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.053.088
Chemical and physical data
FormulaC29H33ClN2O2
Molar mass477.05 g·mol−1
3D model (JSmol)
  • ClC1=CC=C(C2(CCN(CC2)CCC(C3=CC=CC=C3)(C(N(C)C)=O)C4=CC=CC=C4)O)C=C1
  • 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 Y
  • Key:RDOIQAHITMMDAJ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Common side effects include abdominal pain, constipation, sleepiness, vomiting, and a dry mouth. It may increase the risk of toxic megacolon. Loperamide's safety in pregnancy is unclear, but no evidence of harm has been found. It appears to be safe in breastfeeding. It is an opioid with no significant absorption from the gut and does not cross the blood–brain barrier when used at normal doses. It works by slowing the contractions of the intestines.

Loperamide was first made in 1969 and used medically in 1976. It is on the World Health Organization's List of Essential Medicines. Loperamide is available as a generic medication. In 2021, it was the 287th most commonly prescribed medication in the United States, with more than 700,000 prescriptions.

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