Loperamide

Loperamide
Clinical data
Pronunciation/loʊˈpɛrəmaɪd/
Trade namesImodium, others[1]
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[4]
ExcretionFeces (30–40%), urine (1%)
Identifiers
IUPAC name
  • 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)
SMILES
  • ClC1=CC=C(C2(CCN(CC2)CCC(C3=CC=CC=C3)(C(N(C)C)=O)C4=CC=CC=C4)O)C=C1
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 Y
  • Key:RDOIQAHITMMDAJ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Loperamide, sold under the brand name Imodium, among others,[1] is a medication of the opioid receptor agonist class used to decrease the frequency of diarrhea.[5][4] It is often used for this purpose in irritable bowel syndrome, inflammatory bowel disease, short bowel syndrome,[4] Crohn's disease, and ulcerative colitis.[5] It is not recommended for those with blood in the stool, mucus in the stool, or fevers.[4] The medication is taken by mouth.[4]

Common side effects include abdominal pain, constipation, sleepiness, vomiting, and dry mouth.[4] It may increase the risk of toxic megacolon.[4] Loperamide's safety in pregnancy is unclear, but no evidence of harm has been found.[6] It appears to be safe in breastfeeding.[7] It is an opioid with no significant absorption from the gut and does not cross the blood–brain barrier when used at normal doses.[8] It works by slowing the contractions of the intestines.[4]

Loperamide was first made in 1969 and used medically in 1976.[9] It is on the World Health Organization's List of Essential Medicines.[10] Loperamide is available as a generic medication.[4][11] In 2022, it was the 297th most commonly prescribed medication in the United States, with more than 400,000 prescriptions.[12][13]

  1. ^ a b Drugs.com International brands for loperamide Archived 23 September 2015 at the Wayback Machine Page accessed 4 September 2015
  2. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  3. ^ "Loperamide hydrochloride capsule". DailyMed. 30 September 2022. Archived from the original on 14 September 2023. Retrieved 8 January 2024.
  4. ^ a b c d e f g h i "Loperamide Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 7 September 2015. Retrieved 25 August 2015.
  5. ^ a b "About loperamide". nhs.uk. 11 April 2024.
  6. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  7. ^ "Loperamide use while Breastfeeding". Archived from the original on 8 September 2015. Retrieved 26 August 2015.
  8. ^ "loperamide hydrochloride". NCI Drug Dictionary. 2 February 2011. Archived from the original on 7 September 2015. Retrieved 26 August 2015.
  9. ^ Patrick GL (2013). An introduction to medicinal chemistry (Fifth ed.). Oxford: Oxford University Press. p. 644. ISBN 9780199697397. Archived from the original on 14 January 2023. Retrieved 17 December 2020.
  10. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  11. ^ Hamilton RJ (2013). Tarascon pocket pharmacopoeia (14 ed.). [Sudbury, Mass.]: Jones & Bartlett Learning. p. 217. ISBN 9781449673611. Archived from the original on 5 March 2016.
  12. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  13. ^ "Loperamide Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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