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Encyclopedia > Loperamide
Loperamide
Systematic (IUPAC) name
4-[4-(4-chlorophenyl)- 4-hydroxy-1-piperidyl]- N,N-dimethyl- 2,2-diphenyl-butanamide
Identifiers
CAS number 53179-11-6
34552-83-5 (with HCl)
ATC code A07DA03 A07DA05
PubChem 3955
DrugBank APRD00275
Chemical data
Formula C29H33ClN2O2 
Mol. mass 477.037 g/mol (513.506 with HCl)
Pharmacokinetic data
Bioavailability Not significantly absorbed from the gut
Protein binding 97%
Metabolism hepatic
Half life 9.1 to 14.4 hours (average 10.8 hours)
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Loperamide, drawn by User:Jfdwolff in OpenOffice. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A division of the Anatomical Therapeutic Chemical Classification System A Alimentary tract and metabolism A07A Intestinal anti-infectives A07AA Antibiotics A07AA01 Neomycin A07AA02 Nystatin A07AA03 Natamycin A07AA04 Streptomycin A07AA05 Polymyxin B A07AA06 Paromomycin A07AA07 Amphotericin B A07AA08 Kanamycin A07AA09 Vancomycin A07AA10 Colistin A07AA11 Rifaximin A07AA51 Neomycin, combinations A07AA54 Streptomycin, combinations... A division of the Anatomical Therapeutic Chemical Classification System A Alimentary tract and metabolism A07A Intestinal anti-infectives A07AA Antibiotics A07AA01 Neomycin A07AA02 Nystatin A07AA03 Natamycin A07AA04 Streptomycin A07AA05 Polymyxin B A07AA06 Paromomycin A07AA07 Amphotericin B A07AA08 Kanamycin A07AA09 Vancomycin A07AA10 Colistin A07AA11 Rifaximin A07AA51 Neomycin, combinations A07AA54 Streptomycin, combinations... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

GSL(UK) OTC(US) Over the counter (OTC) in Canada The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... Over-the-counter (OTC) drugs are medicines that may be sold without a prescription, in contrast to prescription drugs. ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...

Routes oral, possible insufflation

Loperamide, a synthetic piperidine derivative[1], is a drug effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease. In most countries it is available generically under brand names such as Lopex, Imodium, Dimor and Pepto Diarrhea Control. It was discovered at Janssen Pharmaceutica in 1969. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... This article is about the American grunge band. ... Breed is a song by American grunge band Nirvana, and the fourth track from the bands 1991 breakthrough album Nevermind. ... R-phrases , , Related Compounds Related compounds pyridine pyrrolidine piperazine Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Piperidine is an organic compound with the molecular formula C5H11N. It is a heterocyclic amine with a six-membered... This article does not cite any references or sources. ... Diarrhea, also spelled diarrhoea (see spelling differences), is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause of death in developing countries (particularly among infants), accounting for 5 to 8 million deaths... See also Bacterial gastroenteritis and Diarrhea Gastroenteritis is a general term referring to inflammation or infection of the gastrointestinal tract, primarily the stomach and intestines. ... In medicine, inflammatory bowel disease (IBD) is a group of inflammatory conditions of the large intestine and, in some cases, the small intestine. ... Johnson & Johnson NYSE: JNJ is an international pharmaceutical, medical devices and consumer packaged goods manufacturer founded in 1885. ... Also: 1969 (Stargate SG-1) episode. ...

Contents

Mode of action

Loperamide is an opioid receptor agonist and acts on the μ-opioid receptors in the myenteric plexus large intestines; it does not affect the central nervous system like other opioids. An opioid is a chemical substance that has a morphine-like action in the body. ... The μ opioid receptors (MOR) are a class of opioid receptors with high affinity for enkephalins and beta-endorphin but low affinity for dynorphins. ... Part of the enteric nervous system, Auerbachs plexus (or myenteric plexus) exists between the longitudinal and circular layers of muscularis externa in the gastrointestinal tract and provides motor innervation to both layers and secretomotor innervation to the mucosa. ... A diagram showing the CNS: 1. ...


It works 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.[2] Part of the enteric nervous system, Auerbachs plexus (or myenteric plexus) exists between the longitudinal and circular layers of muscularis externa in the gastrointestinal tract and provides motor innervation to both layers and secretomotor innervation to the mucosa. ... Smooth muscle Layers of Esophageal Wall: 1. ... The gastrocolic reflex or gastrocolic response is one of a number of physiological reflexes controlling the motility, or peristalsis, of the gastrointestinal tract. ...


Loperamide does not cross the blood-brain barrier in significant amounts, and thus has no analgesic properties. Loperamide molecules that do cross the BBB are quickly exported from the brain by P-glycoprotein (PGP), also known as multidrug resistance protein (MDR1). Tolerance in response to long-term use has not been reported. The blood-brain barrier (BBB) is a membranic structure that acts primarily to protect the brain from chemicals in the blood, while still allowing essential metabolic function. ... For other uses of painkiller, see painkiller (disambiguation) An analgesic (colloquially known as painkiller) is any member of the diverse group of drugs used to relieve pain. ... The blood-brain barrier (BBB) is a membranic structure that acts primarily to protect the brain from chemicals in the blood, while still allowing essential metabolic function. ...


However, loperamide can cause physical dependence. Symptoms of opiate withdrawal have been observed in patients abruptly discontinuing long-term therapy with loperamide. For this reason, the drug was briefly classified as a Schedule V controlled substance upon its introduction.[citation needed] Wikipedia does not yet have an article with this exact name. ...


Contraindications

Treatment should be avoided in the presence of fever or if the stool is bloody. Treatment is not recommended for patients who could suffer detrimental effects from rebound constipation. If there is a suspicion of diarrhea associated with organisms that can penetrate the intestinal walls, such as E. coli O157:H7 or salmonella, loperamide is contraindicated. In medicine, a contraindication is a condition or factor that increases the risk involved in using a particular drug, carrying out a medical procedure or engaging in a particular activity. ... An analogue medical thermometer showing the temperature of 38. ... Constipation or irregularity, is a condition of the digestive system where a person (or animal) experiences hard feces that are difficult to egest; it may be extremely painful, and in severe cases (fecal impaction) lead to symptoms of bowel obstruction. ... Escherichia coli O157:H7 is an emerging cause of foodborne illness. ... Species S. enterica This article is about the bacteria. ...


Crossing the blood-brain barrier

When loperamide is taken by itself, it cannot readily cross the blood-brain barrier; however, when loperamide-containing nanoparticles are coated with polysorbate 80 and injected, the results were the same as typical opiates and opioids -- long, effective analgesia. A solution prepared using loperamide coated with polysorbate 80 resulted in a very short duration of action and less effective analgesic effect. The same study concluded that loperamide does not cause any analgesic effects when taken by itself.[3] The blood-brain barrier (BBB) is a membranic structure that acts primarily to protect the brain from chemicals in the blood, while still allowing essential metabolic function. ... Polysorbate 80 is a nonionic detergent [1] which is often used in foods. ... For other uses of painkiller, see painkiller (disambiguation) An analgesic (colloquially known as painkiller) is any member of the diverse group of drugs used to relieve pain. ...


Concurrent administration of P-glycoprotein inhibitors such as quinidine with loperamide has been found to produce respiratory depression, indicative of central opioid action. [4] Quinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent in the heart. ...


Side-effects

Side effects can include drowsiness, constipation, abdominal pain or discomfort, dry mouth, fatigue, and in rare cases toxic megacolon, mild euphoria (at high doses). Toxic megacolon (megacolon toxicum) is a life-threatening complication of other intestinal conditions. ...


See also

See also Bacterial gastroenteritis and Diarrhea Gastroenteritis is a general term referring to inflammation or infection of the gastrointestinal tract, primarily the stomach and intestines. ... Travelers diarrhea (TD) is the most common illness affecting travelers. ...

References

  1. ^ US National Cancer Institute, Drug Dictionary
  2. ^ Katzung, Bertram G. Basic and Clinical Pharmacology, 9th ed. (2004). ISBN 0-07-141092-9
  3. ^ That's Poppycock! - Loperamide : From controlled substance to over-the-counter wonder
  4. ^ http://www.nature.com/clpt/journal/v68/n3/abs/clpt2000101a.html;jsessionid=DF4E10E08776A89B889FC05B3DB509CF

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External links


  Results from FactBites:
 
Loperamide (Imodium®) (688 words)
Loperamide is a synthetic piperidine derivative, a weak narcotic with antidiarrheal properties.
Loperamide should not be used in animals with known hypersensitivity or allergy to the drug.
Loperamide should be avoided in patients with diarrhea caused by toxin ingestion until the toxin is eliminated from the gastrointestinal tract.
loperamide Side Effects, Interactions and Information - Drugs.com (1425 words)
Loperamide slows the rhythm of digestion so that the small intestines have more time to absorb fluid and nutrients from the foods you eat.
Loperamide is also used to reduce the amount of stool in people who have an ileostomy (re-routing of the bowel through a surgical opening in the stomach).
Loperamide is available with a prescription and over-the-counter under several brand and generic names.
  More results at FactBites »

 
 

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