File:Loperamide.svg · Wikimedia Commons · See Wikimedia Commons
loperamide
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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.
OverviewAI-generated
Loperamide is a chemical compound with the formula C₂₉H₃₃ClN₂O₂. Its IUPAC name is 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide. The substance has a mass of 476.223056 and a weight of 477.0. It carries an MCN code of 2933.39.24.
Chemical properties include an xlogp of 5 and a tpsa of 43.8. The molecule contains one hydrogen bond donor and three hydrogen bond acceptors, with a charge of 0. The defined daily dose is 10.
Loperamide is referenced by 1,399 other encyclopedia articles. A PubMed query for the term yields a count of 2778.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
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
~12 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “loperamide” article, available under the CC BY-SA 4.0 licence.