File:Loperamide.svg · Wikimedia Commons · See Wikimedia Commons
loperamide
Sign in to saveAlso known as R-18553
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, short bowel syndrome, Crohn's disease, and ulcerative colitis. Loperamide is taken by mouth.
Key facts
- Drug.image
- Loperamide.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.image2
- Loperamide ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 235
- Drug.USAN
- Loperamide hydrochloride
- Drug.tradename
- Imodium, others
- Drug.MedlinePlus
- a682280
- Drug.DailyMedID
- Loperamide
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- A07
- Drug.ATC_suffix
- DA03
- Drug.ATC_supplemental
- (oxide)
- Drug.legal_AU
- S2
- Drug.legal_BR
- C1
- Drug.legal_CA
- OTC
via Wikipedia infobox
Chemical data
- Formula
- C29H33ClN2O2
- Molecular weight
- 477 g/mol
- IUPAC name
- 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
- SMILES
- CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4
- InChIKey
- RDOIQAHITMMDAJ-UHFFFAOYSA-N
- XLogP
- 5
- Polar surface area
- 43.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
2,778 papers- Loperamide.Journal of pain and symptom management · 2011
- Loperamide Cardiac Toxicity: Pathophysiology, Presentation, and Management.The Canadian journal of cardiology · 2022
- Loperamide: A Readily Available but Dangerous Opioid Substitute.Journal of clinical pharmacology · 2019
- Loperamide misuse and abuse.Journal of the American Pharmacists Association : JAPhA · 2017
- Loperamide toxicity: recommendations for patient monitoring and management.Clinical toxicology (Philadelphia, Pa.) · 2020
via PubMed
Wikidata facts
- Mass
- 476.223056
Show 7 more facts
- chemical formula
- C₂₉H₃₃ClN₂O₂
- MCN code
- 2933.39.24
- canonical SMILES
- CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4
- World Health Organisation international non-proprietary name
- loperamide
- Commons category
- Loperamide
- defined daily dose
- 2
- native label
- Loperamide
via Wikidata · CC0
~12 min read
Article
21 sectionsContents
- Medical uses
- Side effects
- Contraindications
- Children
- Pregnancy and breast feeding
- Drug interactions
- Mechanism of action
- Blood–brain barrier
- Chemistry
- Synthesis
- Physical properties
- History
- Society and culture
- Legal status
- United States
- UK
- Economics
- Brand names
- Off-label/unapproved use
- Research
- References
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, short bowel syndrome, Crohn's disease, and ulcerative colitis. Loperamide is taken by mouth.
Common side effects include abdominal pain, constipation, sleepiness, vomiting, and 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.